Your Money, Your Wealth

Roth Conversions vs. RMDs: Which Tax Bill Hurts More? - 587 Jun 23, 2026

Financial Assessment (Meet with an experienced professional):

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11 rapid-fire spitballs today from Joe Anderson, CFP®, and Big Al Clopine, CPA, on Your Money, Your Wealth® podcast number 587, on everything from Roth conversions and RMDs to whether a guy named Wayne can finally treat himself to a seventy-five-thousand-dollar Audi. Aaron in Syracuse just hit a million bucks in his 401(k) and realizes he needs a spitball on keeping his RMDs low. Do new Roth conversions restart the 5-year clock? 72-year-old Mike in Texas wants to know. Marion inherited a not-yet-five-year-old Roth, and an IRMAA problem along with it. Lu and Stephen each argue that the fellas’ conversion and retirement spitball math might be misleading. Teachers Tony and his wife have pensions that cover everything, so should they even keep saving? John and Peggy need a retirement spitball, Rajesh wonders if he should pay off his mortgage or convert to Roth, and Mike in San Marcos asks about funding a Roth with pension money.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-587 (full show notes & episode transcript)

Retirement Accounts Guide - free download:

https://purefinancial.com/white-papers/retirement-accounts-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-accounts-guide&utm_content=ymyw-pod-ep587-description-whitepaper

401(k) vs. IRA vs. Equity Compensation: The Real Math - YMYW TV:

https://purefinancial.com/ymyw/episodes/recipe-for-retirement-retirement-plans-explained/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep587-description-tv-s10e12

Financial Blueprint (free, self-guided):

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep587-description-blueprint

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:32 - $1.1 Million in My 401(k) at 56: Should I Do Roth Conversions Before RMDs Hit? (Aaron, Syracuse, NY

04:51 - Can You Fund a Roth IRA With Pension Money? (Mike, San Marcos, CA)

06:14 - Can You Roll an UTMA Into a 529 for Tax-Free Education Savings? (Bob the Builder, Westchester, NY)

10:29 - I'm 72 With a 25-Year-Old Roth. Do New Conversions Trigger the 5-Year Clock for Roth Withdrawals? (Mike, TX)

11:43 - Inherited a Roth Less Than 5 Years Old: Are the Earnings Taxable? Can IRMAA Be Avoided? (Marion)

15:59 - You Ignore Future Income! How to Spitball Spending When a Pension and Social Security Are Coming (Stephen)

21:02 - Are Your Roth Conversion Calculations Misleading? Why Future RMDs Need an Inflation Check (Lu)

24:57 - We're Teachers With Pensions That Cover Everything. Should We Stop Saving and Fund the 529s? (Tony, NY

28:23 - $4 Million and Ready to Exit the Rat Race at 61. Do the Numbers Work? (John and Peggy, San Jose, CA

34:37 - $4 Million 401(k) and a 6.5% Rental Mortgage: Pay It Off or Convert to Roth? (Rajesh)

38:42 - We're 62 With $1 Million. Can I Finally Buy the $75K Audi, or Should I Lease? (Wayne, Long Beach, NY)

43:17 - Outro: Next Week on the YMYW Podcast

Roth Conversions: When to Pay Taxes NOW - 586 Jun 16, 2026

Schedule a free financial assessment with an experienced professional at Pure Financial Advsiors: https://purefinancial.com/lp/free-assessment/?utm_source=captivate&utm_medium=podcast&utm_campaign=free-assessment&utm_content=ymyw-pod-ep586-description-free-assessment

“Walter and Skyler” in Iowa ask if they’re on track to retire early, or if they’re just "cooking up overconfidence?" And how aggressively should they convert their retirement savings to tax-free Roth money before the pension and Social Security kick in? California Dreamin’ has it down to one decision: convert to the top of the 22 percent tax bracket, or push into the 24? “Mike and Carol” in Florida ask, when you're weighing a conversion, should you be looking at your tax bracket, or your actual effective tax rate? Finally, is it worth the cost for “Westley and Buttercup” to use the brand new option to turn a big employer contribution into Roth money? Joe Anderson, CFP® and Big Al Clopine, CPA from Pure Financial Advisors spitball on all of these questions, today on YMYW podcast 586.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-586 (full show notes & episode transcript)

10 Common Roth IRA Mistakes That Can Cost You $50,000 (or More!) - YMYW TV:

https://purefinancial.com/white-papers/roth-ira-white-paper/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-ultimate-guide-to-roth-iras&utm_content=ymyw-pod-ep586-description-whitepaper

The Ultimate Guide to Roth IRAs - free download:

https://purefinancial.com/ymyw/episodes/10-common-roth-ira-mistakes-that-can-cost-you-50000-or-more/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep586-description-tv-s12e04

Financial Blueprint (free, self-guided):

https://bit.ly/YMYWblueprintC

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:10 - Early Retirement Overconfidence? Aggressive Roth Conversions? (Walter & Skyler, Iowa)

13:25 - Roth Conversion Bracket Call: 22% or 24%? (CA Dreamin', Central Coast)

22:27 - Tax Bracket vs. Effective Rate: The Roth Math Most People Get Wrong (Mike & Carol, FL)

32:16 - Should the NEC Go to the Roth? The 401(k) Decision (Westley & Buttercup, TX)

42:28 - Outro: Next Week on the YMYW Podcast

Don't Overcomplicate Retirement: Margin Loans, Whole Life, Roth Mistakes - 585 Jun 08, 2026

Financial Assessment (Meet with an experienced professional):

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Free Financial Resources in This Episode: https://bit.ly/ymyw-585 (full show notes & episode transcript)

Today on Your Money, Your Wealth® podcast number 585, Joe and Big Al spitball for folks who are already winning and thinking about getting fancy with it. Reno in Oregon is 50, and his pension is so big he's not sure how to invest or why he would need to convert to Roth. Michael is considering taking out a half-million-dollar margin loan to juice investment returns. What do the fellas think? Tune in for the surprising debate. Husker Fans just pocketed two million from selling their business here come the product pitches: should they buy annuities, set up a charitable trust, or just swallow the tax? What do the fellas think of whole life insurance? And finally, John and Lib on Waltons Mountain - or rather, the Catskills - aren’t sure if they’ve saved too little or too much. Can they bridge the gap until their pension?

Emotionless Investing Guide - free download:

https://purefinancial.com/white-papers/emotionless-investing-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-emotionless-investing-guide&utm_content=ymyw-pod-ep585-description-whitepaper

Financial Blueprint - free, self-guided:

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep585-description-blueprint

Retirement Rebound: 5 Plays to Help You Score a Comeback - YMYW TV:

https://purefinancial.com/ymyw/episodes/retirement-rebound-5-plays-help-score-comeback/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep585-description-tv-s10e11

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:58 - How Should a Pension-Rich 50-Year-Old Invest? Should They Even Bother with Roth Conversions? (Reno, OR)

10:30 - Should I Borrow $500K in a Margin Loan to Invest? (Michael, VA)

23:01 - We're Getting $2M From Selling the Business. Annuity, Charitable Trust, or Bite the Tax? What About Whole Life Insurance? (Husker Fans, Nebraska)

34:14 - Can a Frugal Mountain Couple Bridge the Gap to a $60K Pension? (John & Lib, NY Catskills)

41:13 - Outro: Next Week on the YMYW Podcast

These Tax Strategies Let You Spend More in Retirement - 584 Jun 02, 2026

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

Heidi from the Space Coast of Florida found a money-saving tidbit in a past episode that completely changed how she thinks about her financial advisor's fee. Joe Anderson, CFP® and Big Al Clopine, CPA expand on the strategy, today on Your Money, Your Wealth® podcast number 584. Laverne and Shirley have four million bucks, Roth conversion questions, annuity questions, and a retirement plan so detailed it may require a diagram. Finally, Bess and George from Pure Michigan are already retired, already on Social Security, and already losing sleep over their investments. So why are they so stressed? Joe and Big Al’s a debate about a 1% advisory fee gets a little spicy in that one.

Retirement Accounts Guide - free download:

https://purefinancial.com/white-papers/retirement-accounts-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-accounts-guide&utm_content=ymyw-pod-ep584-description-whitepaper

Financial Blueprint - free, self-guided retirement plan check-in:

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep584-description-blueprint

Retirement Course: Can You Hit a Hole in One? With PGA Pro Chris Riley - YMYW TV:

https://purefinancial.com/ymyw/episodes/retirement-course-hole-in-one-pga-pro-chris-riley/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep584-description-tv-s11e02

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:02 - Can Financial Advisor AUM Fees Come Out of Pre-Tax Money? (Heidi, Space Coast, FL)

09:54 - Are We Converting Enough Before RMDs? What to Do With Annuities? (Laverne & Shirley, Cleveland, OH)

30:23 - Target Date Funds and a Sad Brokerage: Good Enough? Can't See Ever Paying an Advisor (Bess & George, MI)

45:37 - Outro: Next Week on the YMYW Podcast

$1.6M in One Stock? Here's How to Get Out Without Getting Crushed - 583 May 26, 2026

Schedule a Free Financial Assessment with an experienced professional:

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Joe Anderson, CFP® and Big Al Clopine, CPA spitball for people sitting on life-changing gains who are just one wrong move away from handing a third of it to the IRS. How should they diversify their concentrated stock positions? That’s today on Your Money, Your Wealth podcast number 583. First up, Walter's a software engineer who got lucky 15 years ago. Now he's got $1.6 million in company stock, and a retirement clock ticking down in six years. Richard from Staten Island listened to his son six years ago, went big on oil, saw a huge gain, and now 80% of his portfolio is in that one position. His custodian wants him to sell, but he’s not so sure. Finally, Doctors “Bones McCoy and Beverly Crusher” just discovered they’ll be inheriting millions still sitting in an old 401(k) loaded with company stock.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-583 (full show notes & episode transcript)

2026 Tax Planning Guide - free download:

https://purefinancial.com/white-papers/tax-planning-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-tax-planning-guide&utm_content=ymyw-pod-ep583-description-whitepaper

10 Steps to Improve Investing Success - free download:

https://purefinancial.com/white-papers/10-steps-to-improve-investing-success/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-10-steps-to-improve-investing-success&utm_content=ymyw-pod-ep583-description-whitepaper

Once Retirees See This Data, They Stop Worrying About Investing - YMYW TV:

https://purefinancial.com/ymyw/episodes/once-retirees-see-this-data-they-stop-worrying-about-investing/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep583-description-tv-s12e03

Strategies for Diversifying Concentrated Stock Positions - blog post:

https://purefinancial.com/ask-pure/strategies-for-diversifying-concentrated-stock-positions/?utm_source=captivate&utm_medium=podcast&utm_campaign=learning-center&utm_content=ymyw-pod-ep583-description-learning-center

Comic-Con 2014: https://www.youtube.com/watch?v=EQASw5viQPI

2016: https://www.youtube.com/watch?v=WcSRFo7W5ZQ

Financial Blueprint (free, self-guided):

https://bit.ly/YMYWblueprintC

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:09 - How Do You Sell $1.6M in Company Stock Without Writing the IRS a Giant Check? (Walter & Jesse, NM)

13:04 - One Oil Stock is 80% of My Portfolio. My Financial Advisors Want Me to Sell It. I Don't Trust Them. (Richard, Staten Island, NY)

30:10 - We're Two Doctors About to Inherit a $1.35M Tax Bomb. What Now? (Bones & Beverly, MI)

45:23 - Outro: Next Week on the YMYW Podcast

Safe Withdrawal Rate Debate: How Much Can You REALLY Spend in Early Retirement? - 582 May 19, 2026

Schedule a Free Financial Assessment with an experienced professional:

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Today on Your Money, Your Wealth® podcast number 582, Joe Anderson, CFP® and Big Al Clopine, CPA address something a not-insignificant portion of this audience has been complaining about for years: their so-called 'absurdly conservative' safe withdrawal rates for early retirement. Rand and Elayne from Ohio are here to gripe about it directly with a thought experiment: a million bucks at age 36 and a three-year sabbatical in France. When, if ever, would Joe and Big Al say they should cut it short and go back to work if the markets turned ugly? Mike2me17 piles on, with his own SWR take about AUM fees in his Apple Podcasts review. But first, a real world example: Ron and Harry from Florida are elite performers with a high-risk specialty job. Can they safely pull off moving to Portugal and living on $38,000 a year in their early 40s? If you’re one of the people yelling at your podcast app every time Joe or Al mentions a 2% withdrawal rate, today's your day, and we welcome you to leave more of your thoughts on the topic in Apple Podcasts, YouTube, on Reddit, in our inboxes - like everyone else has.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-582 (full show notes & episode transcript)

Withdrawal Strategy Guide - YMYW TV:

https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-withdrawal-strategy-guide&utm_content=ymyw-pod-ep582-description-whitepaper

Financial Blueprint (free, self-guided):

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep582-description-blueprint

Retirement Pop Quiz: 18 Questions to Get You Ready to Retire - YMYW TV

https://purefinancial.com/ymyw/episodes/retirement-pop-quiz-18-questions-ready-to-retire/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep582-description-tv-s10e10

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:14 - Elite Performers Semi-Retiring at 43 and Moving to Portugal. Can We Pull It Off? (Ron & Harry, FL)

16:16 - YMYW Safe Withdrawal Rate Assumptions Are Absurd. At What Point Do You Go Back to Work If Markets Crash? (Rand & Elayne, ID)

34:13 - YMW Safe Withdrawal Rates to Protect AUM Fee (Comment from mike2me17, Apple Podcasts)

41:46 - Outro: Next Week on the YMYW Podcast

Roth Conversions, Pension Lump Sums & Annuities: Is Bigger Always Better? - 581 May 12, 2026

Schedule a Free Financial Assessment with an experienced professional:

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June in Washington State is 62 with $2.5 million saved and a $350,000 pension on the table. Should she take the lump sum or the monthly check for life? Spoiler alert: there's a 3-to-1 vote in the studio, and Big Al is the one, today on Your Money, Your Wealth® podcast number 581 with Joe Anderson, CFP®, and Big Al Clopine, CPA. Plus, how aggressive should “Homer and Marge” get with Roth conversions, and is it smart to pay the conversion tax from an inherited IRA RMD? Pompous Assets drops his big, fat wallet on the YMYW table next: with millions in tax-deferred and taxable accounts, why is his financial advisor fighting him on a Roth conversion? Of course, Joe and Big Al have some thoughts on the subject. Finally, Johnny Mercer in Georgia is eyeing an immediate income annuity and a MYGA. The fellas break down why that 7.5% “rate of return” might not be what he thinks.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-581 (full show notes & episode transcript)

Ultimate Guide to Roth IRAs - free download:

https://purefinancial.com/white-papers/roth-ira-white-paper/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-ultimate-guide-to-roth-iras&utm_content=ymyw-pod-ep581-description-whitepaper

Financial Blueprint (free, self-guided):

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep581-description-blueprint

Your 11 Step Path to Financial Freedom - YMYW TV:

https://purefinancial.com/ymyw/episodes/your-11-step-path-to-financial-freedom/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep581-description-tv-s10e13

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:08 - Should I Take the Pension Lump Sum or Monthly Income? (June, WA State)

09:23 - How Much Should We Convert to Roth Each Year? (Homer & Marge)

16:26 - Should I Convert My Entire IRA to a Roth? (Pompous Assets, Arkansas)

23:00 - $5M All in Pre-Tax. Should I Buy an Annuity Before It's Too Late? (Johnny Mercer, GA)

36:00 - Outro: Next Week on the YMYW Podcast

You Have Enough to Retire Before 60. Why Are You Still Working? - 580 May 05, 2026

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Today on Your Money, Your Wealth® podcast number 580, Joe Anderson, CFP®, and Big Al Clopine, CPA, are spitballing for some folks who've done the work, hit the numbers, but aren’t sure if they can really walk away yet. Martha in DC is 44 and says her soul is being sucked out of her body by her employer. When can she stop working full-time and foster puppies instead? “Bandit” is bullish on his company stock in archeology instruments, but not so much on his work itself. “Kevin” is staring down a wall of deferred comp and needs a spitball on how aggressive his and “Winnie’s” Roth conversion strategy should be before RMDs hit. Can both “Bandit and Chilli” and “Kevin and Winnie” call it quits this year?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-580 (full show notes & episode transcript)

Tax-Free Retirement Guide - free download:

https://purefinancial.com/white-papers/tax-free-retirement-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-tax-free-retirement-guide&utm_content=ymyw-pod-ep580-description-whitepaper

Retirement Readiness Guide - free download:

https://purefinancial.com/white-papers/retirement-readiness-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-readiness-guide&utm_content=ymyw-pod-ep580-description-whitepaper

401(k) After Retirement? Here Are Your 4 Options (And The Costly Mistakes) - YMYW TV:

https://purefinancial.com/ymyw/episodes/what-happens-to-your-401k-ira-at-retirement/?utm_source=libsyn&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep580-description-tv-s10e06

Financial Blueprint (free, self-guided):

https://bit.ly/YMYWblueprintC

REQUEST your Retirement Spitball Analysis:

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DOWNLOAD more free guides:

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Connect With Us:

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:56 - Can We Exit the Rat Race in Our 40s With $6.5M? (Martha & George, DC)

16:07 - Can I Retire at 51 Without Using Rule of 55? (Bandit & Chilli, CA)

36:29 - Can I Retire Before My $3M Deferred Comp Pays Out? (Kevin & Winnie, Chicago)

44:28 - Outro: Next Week on the YMYW Podcast

Too Much 401k Money? The $3M Roth Conversion Problem - 579 Apr 28, 2026

Saving into Roth instead of traditional accounts to bring down required minimum distributions in retirement, and whether retiring early is in the cards: that's today on Your Money, Your Wealth® podcast 579 with Joe Anderson, CFP®, and Big Al Clopine, CPA. Brian in New York and "Todd and Margo" in Utah each have over $3 million in their pre-tax accounts. What should their Roth conversion strategies look like, and can Todd retire this year? But first up, should "Captain Morgan" go Roth to avoid RMDs and can he retire in a couple of years? Should "Klo Jopine" contribute to Roth instead of traditional if his income will always remain the same? Finally, Kyle and Katie have high incomes and need a spitball on how they can avoid future RMDs. Ya think Roth conversions might be in their future? We'll find out.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-579 (full show notes & episode transcript)

LIMITED TIME SPECIAL OFFER: THE DIY RETIREMENT GUIDE - download before the Special Offer changes on Friday, May 1, 2026!

https://purefinancial.com/ymyw/?utm_source=libsyn&utm_medium=podcast&utm_campaign=whitepaper-diy-retirement-guide&utm_content=ymyw-pod-ep579-description-whitepaper#specialoffer

Financial Advisors Expose Internet's Worst Retirement Strategies! - YMYW TV:

https://purefinancial.com/ymyw/episodes/financial-advisors-expose-internets-worst-retirement-strategies/?utm_source=libsyn&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep579-description-tv-s11e11

Financial Blueprint (self-guided):

https://bit.ly/PureFinancialBlueprint

Financial Assessment (Meet with an experienced professional):

https://bit.ly/PureFreeAssessment

REQUEST your Retirement Spitball Analysis:

https://bit.ly/AskJoeAndAl

DOWNLOAD more free guides:

https://bit.ly/PureGuides

READ financial blogs:

https://bit.ly/PureFinBlog

WATCH educational videos:

https://bit.ly/PureEdVideos

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWNewsletter

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

https://bit.ly/YMYW-YT

Subscribe or follow YMYW in your favorite podcast app:

https://lnk.to/ymyw

Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This Week on the YMYW Podcast 00:58 - Should I Go Roth to Avoid RMDs and Retire at 51? (Captain Morgan, CA) 11:33 - Roth vs Traditional for Flat Income Earners? (Klo Jopine, TN) 22:53 - Big Roth Conversions to Tame a $3.5M 403(b)? (Brian, NY) 27:36 - Can I Retire in 2026 and Spend $200K/yr? (Todd 54 & Margo, UT) 34:53 - How High Income Earners Can Reduce Future RMDs (Kyle & Katie, Midwest) 44:37 - Outro: Next Week on the YMYW Podcast

The Retirement Question Every Couple Asks: Can We Afford It? - 578 Apr 21, 2026

"Chase and Ryder" are 56 and 55 with $5 million saved and huge pensions the day they retire. So why are they so nervous about pulling the trigger? That's today on Your Money, Your Wealth® podcast number 578 with Joe Anderson, CFP® and Big Al Clopine, CPA. "Andy and April" are 46 with $2.4 million saved and 10 years until they want to retire. Can they get there, and do they need a trust? "Burt and Sally" are in their late forties with solid pensions and a retirement dream, but is the math close enough to make it work? Finally, does "Dolly" have any options for squeezing more out of Social Security when she and her spouse have identical benefits? She's inheriting a brokerage account too, and wonders about the asset mix.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-578 (full show notes & episode transcript)

Withdrawal Strategy Guide - free download:

https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=libsyn&utm_medium=podcast&utm_campaign=whitepaper-withdrawal-strategy-guide&utm_content=ymyw-pod-ep578-description-whitepaper

Retirement Spending: How Much is Too Much? - YMYW TV:

https://purefinancial.com/ymyw/episodes/retirement-spending-how-much-is-too-much/?utm_source=libsyn&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep578-description-tv-s12e02

Financial Blueprint (self-guided):

https://bit.ly/PureFinancialBlueprint

Financial Assessment (Meet with an experienced professional):

https://bit.ly/PureFreeAssessment

REQUEST your Retirement Spitball Analysis:

https://bit.ly/AskJoeAndAl

DOWNLOAD more free guides:

https://bit.ly/PureGuides

READ financial blogs:

https://bit.ly/PureFinBlog

WATCH educational videos:

https://bit.ly/PureEdVideos

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWNewsletter

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

https://bit.ly/YMYW-YT

Subscribe or follow YMYW in your favorite podcast app:

https://lnk.to/ymyw

Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:58 - $5.5M, Big Pensions: Safe to Retire at 57? (Chase & Ryder, San Diego)

10:39 - We're 46. Can We Retire in 10 Years? Do We Need a Trust? (Andy & April, CA)

21:28 - Can We Retire in 2027 With a Pension + $655K? (Burt & Sally, Nonesuch, KY)

34:19 - How to Max Social Security with No Spousal Benefit? (Dolly, TN)

41:41 - Outro: Next Week on the YMYW Podcast

This Early Retirement Strategy Could Be a Huge Mistake - 577 Apr 14, 2026

Joe Anderson, CFP® and Big Al Clopine, CPA spitball on whether a popular early retirement strategy could actually blow up your financial plan, today on Your Money, Your Wealth® podcast number 577. Red and Kitty from Wisconsin are burned out at 40 and wonder if retiring at 45 using the 72(t) tax election to take substantially equal periodic payments, or SEPP, is a smart bridge strategy. Jiminy Billy Bob in North Carolina is also considering a 72(t). How should he structure his withdrawal order, and does he need to shift into bonds before downshifting his career? Plus, Steve and Sharon in Minnesota have 8 million bucks. Steve is getting laid off at age 56. What should they do with their 401(k), stock options, incentives, and benefits before and after the layoff?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-577 (full show notes & episode transcript)

Recession Protection Guide - free download

Retirement Readiness Guide - free download

6 Ways Americans Accidentally Sabotage Their Retirement - YMYW TV

Financial Blueprint (self-guided):

https://bit.ly/PureFinancialBlueprint

Financial Assessment (Meet with an experienced professional):

https://bit.ly/PureFreeAssessment

REQUEST your Retirement Spitball Analysis:

https://bit.ly/AskJoeAndAl

DOWNLOAD more free guides:

https://bit.ly/PureGuides

READ financial blogs:

https://bit.ly/PureFinBlog

WATCH educational videos:

https://bit.ly/PureEdVideos

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWNewsletter

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

https://bit.ly/YMYW-YT

Subscribe or follow YMYW in your favorite podcast app:

https://lnk.to/ymyw

Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This week on the YMYW Podcast

01:06 - Why Retiring at 45 Using 72(t) SEPP Withdrawals is Risky (Red & Kitty, WI)

13:28 - Early Retirement Strategy: Withdrawal Order, Bonds, and 72(t) (Jiminy Billy Bob, NC)

22:49 - Laid Off at 56 With $7.9M: How to Handle Your Exit Strategy (Steve & Sharon, St. Paul, MN)

43:51 - Outro: Next Week on the YMYW Podcast

When Roth Conversions Don't Make Sense (And When They're a No-Brainer) - 576 Apr 07, 2026

Are Roth conversions worth it? We'll find out, today on Your Money, Your Wealth® podcast number 576. TJ in PA is gonna have huge capital gains. Joe and Big Al spitball on whether it's worth it for him to convert. Rebels Without a Gauze in New England are over 70. Is it too late for them to convert? How much should Biking Barnsey convert from his tax-deferred accounts to Roth each year, and are there any single ladies in the YMYW audience that would like to help him spend his retirement money? Finally, the fellas spitball on whether Zisi and his wife are being too aggressive with their conversion strategy.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-576 (full show notes & episode transcript)

Complete Roth Papers Package - free download:

https://purefinancial.com/white-papers/the-complete-roth-papers-package/?utm_source=libsyn&utm_medium=podcast&utm_campaign=whitepaper-the-complete-roth-papers-package&utm_content=ymyw-pod-ep576-description-whitepaper

Financial Assessment (Meet with an experienced professional):

https://bit.ly/PureFreeAssessment

Financial Blueprint (self-guided):

https://bit.ly/PureFinancialBlueprint

REQUEST your Retirement Spitball Analysis:

https://bit.ly/AskJoeAndAl

DOWNLOAD more free guides:

https://bit.ly/PureGuides

READ financial blogs:

https://bit.ly/PureFinBlog

WATCH educational videos:

https://bit.ly/PureEdVideos

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWNewsletter

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

https://bit.ly/YMYW-YT

Subscribe or follow YMYW in your favorite podcast app:

https://lnk.to/ymyw

Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This Week on the YMYW Podcast 00:55 - We Have Over $7M. Capital Gains are Huge. Are Roth Conversions Worth It? (TJ in PA) 12:37 - Too Late for Roth Conversions at Age 70+? (Rebels Without a Gauze, CT) 23:19 - Am I Spending Too Much or Not Enough in Retirement? How Much Should I Convert? (Biking Barnsey, Arkansas) 33:37 - We have $18M. Are We Doing Too Many Roth Conversions Before Age 75? (Zisi) 41:14 - Outro: Next Week on the YMYW Podcast 42:16 - The Derails: Big Al's New Jacket

Die With Zero: Are You Giving Your Kids Too Much? - 575 Mar 31, 2026

Joe Anderson, CFP® and Big Al Clopine, CPA spitball on how to build your own retirement AND support your kids financially, today on Your Money, Your Wealth® podcast number 575. "Lloyd and Diane" in Montgomery County are 50 with $8.4 million. Can they retire early and still be generous with their kids? E and T in Missouri are 34 and 31 with $255K, and hopefully some big inheritances in the future. Can they fund the kids' college, and help them buy their first homes, AND retire early? Kent in Kansas City is 73 with 12 million bucks and $2 million in life insurance. Do Joe and Big Al back up his plan to buy an annuity, gift money to his kids now, and still spend freely in retirement, Die With Zero style? Finally, should John in the San Francisco Bay Area sell the family home and move to Nevada, or hold the house for his autistic daughters to inherit later?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-575 (full show notes & episode transcript)

Estate Plan Organizer - free download:

https://purefinancial.com/white-papers/estate-plan-organizer/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-575

Retirement Readiness Guide - free download:

https://purefinancial.com/white-papers/retirement-readiness-guide/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-575

Four Hard Truths About Retirement You Need to Face - YMYW TV:

https://purefinancial.com/ymyw/episodes/4-hard-retirement-truths-about-retirement-you-need-to-face/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-575

Financial Blueprint (self-guided):

https://bit.ly/PureFinancialBlueprint

Financial Assessment (Meet with an experienced professional):

https://bit.ly/PureFreeAssessment

REQUEST your Retirement Spitball Analysis:

https://bit.ly/AskJoeAndAl

DOWNLOAD more free guides:

https://bit.ly/PureGuides

READ financial blogs:

https://bit.ly/PureFinBlog

WATCH educational videos:

https://bit.ly/PureEdVideos

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWNewsletter

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

https://bit.ly/YMYW-YT

Subscribe or follow YMYW in your favorite podcast app:

https://lnk.to/ymyw

Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:10 - 50 with $8.4M. Can We Retire Early and Still Give to Our Kids? (Lloyd Dobler and Diane, Montgomery County, MD)

11:41 - Die With Zero: Spend My $12M or Buy an Annuity? (Kent, 73 & 70, Kansas City)

25:08 - Can We Afford Kids' College AND Houses AND Our Own Early Retirement? (E & T, 34 & 31, Missouri)

34:17 - Should We Move to Save Money or Keep the House for Our Autistic Kids? (John, 68 & 66, San Francisco Bay Area)

42:29 - Outro: Next Week on the YMYW Podcast

When Should You Take Social Security? (Don't Screw This Up) - 574 Mar 24, 2026

Joe Anderson, CFP® and Big Al Clopine, CPA focus on Social Security claiming strategies as part of the retirement spitballs, today on Your Money, Your Wealth® podcast number 574. Bijou Plutus and her husband in Massachusetts are 62 and 64 with about a million dollars. Can she retire at 65, and should he claim Social Security early? Dr. Jekyll and Mrs. Hyde in the Twin Cities have about the same at 51 and 49, plus big pensions and high spending. Can they afford to retire early, and when should they claim Social Security? Diggler and Roller Girl in Tennessee are 57 and 58 with about $600K, and Diggler estimates his Social Security break-even is at age 77. Can he collect Social Security early and simply work recreationally?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-574 (full show notes & episode transcript)

Social Security Handbook - free download:

https://purefinancial.com/white-papers/social-security-handbook/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-574

Tax-Free Retirement Guide - free download:

https://purefinancial.com/white-papers/tax-free-retirement-guide/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-574

How To Retire Tax-Free With A Smart Income Plan - YMYW TV:

https://purefinancial.com/ymyw/episodes/how-to-retire-tax-free-smart-income-plan/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-574

Financial Blueprint (self-guided):

https://bit.ly/PureFinancialBlueprint

Financial Assessment (Meet with an experienced professional):

https://bit.ly/PureFreeAssessment

REQUEST your Retirement Spitball Analysis:

https://bit.ly/AskJoeAndAl

DOWNLOAD more free guides:

https://bit.ly/PureGuides

READ financial blogs:

https://bit.ly/PureFinBlog

WATCH educational videos:

https://bit.ly/PureEdVideos

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWNewsletter

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

https://bit.ly/YMYW-YT

Subscribe or follow YMYW in your favorite podcast app:

https://lnk.to/ymyw

Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This week on the YMYW Podcast

01:07 - 62 and 64 with About $1M. Can I Retire at 65? Should Hubby Claim Social Security Early? (Bijou Plutus, MA)

11:52 - Can We Retire in Our 50s With Pensions and High Spending? (Dr. Jekyll & Mrs. Hyde, Twin Cities, MN)

29:53 - Social Security Break-Even at 77. Claim Early and Work Recreationally? (Diggler & Rollergirl, 57 & 58, Tennessee)

42:52 - Outro: Next Week on the YMYY Podcast

Could You Retire Tomorrow If You Had To? - 573 Mar 17, 2026

Juan and Mary in Brooklyn are 49 and 48 with $2.2 million saved. Can Juan afford to retire early, or just walk away if he gets fired? And if they get divorced, yikes - but does the math still work? That's today on Your Money, Your Wealth® podcast number 573. But first, "Reuben Sailing Shoes" is 68, single, retired, and has $1.6 million saved, but he's never had a budget in his life. How much can he actually spend? "Leslie and Ben" are federal retirees in their seventies with great pensions and a mix of pre-tax and Roth savings, and "Mork and Mindy" in Delaware are retired with an annuity, a pension, Social Security, and $1.3 million in an IRA. Joe Anderson, CFP® and Big Al Clopine, CPA spitball on how Roth conversions and RMD timing can help both couples minimize taxes and make the most of what they've got.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-573 (full show notes & episode transcript)

Complete Roth Papers Package - free download:

https://purefinancial.com/white-papers/the-complete-roth-papers-package/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-573

Retirement Course: Can You Hit a Hole in One? With PGA Pro Chris Riley - YMYW TV:

https://purefinancial.com/ymyw/episodes/retirement-course-hole-in-one-pga-pro-chris-riley/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-573

Financial Blueprint (self-guided):

https://bit.ly/PureFinancialBlueprint

Financial Assessment (Meet with an experienced professional):

https://bit.ly/PureFreeAssessment

REQUEST your Retirement Spitball Analysis:

https://bit.ly/AskJoeAndAl

DOWNLOAD more free guides:

https://bit.ly/PureGuides

READ financial blogs:

https://bit.ly/PureFinBlog

WATCH educational videos:

https://bit.ly/PureEdVideos

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWNewsletter

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

https://bit.ly/YMYW-YT

Subscribe or follow YMYW in your favorite podcast app:

https://lnk.to/ymyw

Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This week on the YMYW Podcast

01:04 - How Much Can a Single 68-Year-Old Retiree With $1.6M(?) Spend Without Running Out of Money? (Reuben Sailing Shoes, Wyoming)

08:38 - 72 and 76 With $1.4M. Should We Keep Doing Roth Conversions After RMDs Start? (Leslie and Ben, Ohio)

17:12 - 71 and 73 With $1.73M. How to Balance Roth Conversions, RMDs, Widow Taxes, and Inheritance Goals? (Mork and Mindy, Delaware)

28:28 - 49 and 48 with $2.2M. If I Get Fired, Quit, or Get Divorced Tomorrow, Will We Be Fine? (Juan & Mary, Brooklyn, NY)

39:20 - Outro: Next Week on YMYW Podcast

Could You Lose Half Your Retirement Income to Taxes? - 572 Mar 10, 2026

"Carl and Jane" have eight million bucks, and their advisor is suggesting a 130/30 long-short investing strategy. Joe Anderson, CFP® and Big Al Clopine, CPA spitball on whether this is a smart tax move or unnecessary complexity - and whether they would do it themselves, today on Your Money, Your Wealth® podcast number 572. Plus, Tyrone and Tova think they may never even need their retirement accounts, so do they really need to bother with Roth conversions if the kids are going to inherit the money anyway, or could skipping the conversions mean losing half their retirement income to taxes? Mark in San Diego is juggling Roth conversions and Social Security timing without blowing up his tax bill, or the income-related monthly adjustment amount for Medicare, or net investment income tax. And "Boat Drinks" has a big non-qualified deferred compensation plan. How can he structure payouts before it turns into a tax nightmare - and before he potentially gets laid off?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-572 (full show notes & episode transcript)

The Emotionless Investing Guide - free download

https://purefinancial.com/white-papers/emotionless-investing-guide/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-572

The Ultimate Guide to Roth IRAs - free download

https://purefinancial.com/white-papers/roth-ira-white-paper/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-572

The Truth About Your Love/Hate Relationship with Money - YMYW TV

https://purefinancial.com/ymyw/episodes/truth-about-love-hate-relationship-with-money/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-572

Financial Blueprint (self-guided):

https://bit.ly/PureFinancialBlueprint

Financial Assessment (Meet with an experienced professional):

https://bit.ly/PureFreeAssessment

REQUEST your Retirement Spitball Analysis:

https://bit.ly/AskJoeAndAl

DOWNLOAD more free guides:

https://bit.ly/PureGuides

READ financial blogs:

https://bit.ly/PureFinBlog

WATCH educational videos:

https://bit.ly/PureEdVideos

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWNewsletter

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

https://bit.ly/YMYW-YT

Subscribe or follow YMYW in your favorite podcast app:

https://lnk.to/ymyw

Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:12 - Should Investors with $8M Use a 130/30 Long-Short Investing Strategy? (Carl Sandburg and Jane Addams, California)

12:42 - We'll Never Need Our Retirement Accounts. Should We Still Do Roth Conversions? (Tyrone and Tova)

27:18 - Roth Conversions vs. Social Security: Which Comes First? What About IRMAA and NIIT? (Mark, California)

38:16 - How to Structure Non-Qualified Deferred Compensation Payouts When a Layoff Might Be Coming? (Boat Drinks)

50:10 - Outro: Next Week on the YMYW Podcast

Retire Early in Your 40s or 50s: Green Light or Reality Check? - 571 Mar 03, 2026

If you plan to punch the clock for the final time decades before "standard" retirement age, you need a financial strategy that goes beyond just saving. Joe Anderson, CFP® and Big Al Clopine, CPA spitball five different early retirement plans to see whose numbers are tight and who is ready to go for it, today on Your Money, Your Wealth® podcast 571. George in South Carolina wants to retire in 8 years at 53. Does he have enough in his brokerage account to bridge the gap to Social Security? Joe in Massachusetts is saving a staggering $200,000 a year, but will his high-spending lifestyle make a multi-million dollar nest egg look small? The fellas help 26-year-old Jonathan in Florida map out a path to retire in his 40s using his 457 plan, and they spitball on whether early exit strategies for both Kris and Rojo in California are a "green light" or a reality check. Plus, Joe explains why the "Rule of 55" and Roth conversions might be some of the most important tools in your early retirement toolbox.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-571 (full show notes & episode transcript)

Withdrawal Strategy Guide - free download:

https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-571

Long-Term Care Planning Guide - free download:

https://purefinancial.com/white-papers/long-term-care-planning-options/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-571

The #1 Spending Mistake Ruining Retirements - YMYW TV:

https://purefinancial.com/ymyw/episodes/number-one-spending-mistake-ruining-retirements/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-571

Financial Blueprint (self-guided):

https://bit.ly/PureFinancialBlueprint

Financial Assessment (Meet with an experienced professional):

https://bit.ly/PureFreeAssessment

REQUEST your Retirement Spitball Analysis:

https://bit.ly/AskJoeAndAl

DOWNLOAD more free guides:

https://bit.ly/PureGuides

READ financial blogs:

https://bit.ly/PureFinBlog

WATCH educational videos:

https://bit.ly/PureEdVideos

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWNewsletter

Connect With Us:

Subscribe on YouTube and join the conversation in the comments:

https://bit.ly/YMYW-YT

Subscribe or follow YMYW in your favorite podcast app:

https://lnk.to/ymyw

Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:06 - Is Retiring at 53 With No Pension a Smart Move or a Risky Bet? (George, South Carolina)

11:59 - High Income, High Spend, Early Retirement: Does the Math Still Work? (Joe, MA)

18:39 - At 26, Should I Go All In on a 457 to Retire Way Early? (Jonathan, Florida)

26:41 - Can I Retire Early and Still Cover Health Care and Long Term Care Costs? (Kris, California)

33:33 - I'm a Widowed Parent. Can I Retire at 57 and Still Fund College and Legacy Goals? (Rojo, California)

43:08 - Outro: Next Week on the YMYW Podcast

Retirement Planning for Aging Parents - and Can You Retire Early? - 570 Feb 24, 2026

Joe and Big Al spitball two sides of the retirement equation, today on Your Money, Your Wealth® podcast number 570. Daniel in Texas is 40 and worrying about how to support Mom and Dad if their money runs out. Can he build some kind of financial safety net for them without ruining his own retirement? Jemma's 82-year-old mom is drawing down her portfolio. Is locking in guaranteed income with an annuity a smart move, or could that create new problems down the road? Plus, "Cookie and Gerry" want to walk away from work before 50 with a big brokerage account and a pension. Are they positioned correctly? How can they avoid pulling the wrong levers at the wrong time? And "Fred and Wilma" are staring at a potential multi-million-dollar ESOP payout. What levers do they need to pull so they can retire at 46 and shout "Yabba Dabba Doo"?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-570 (full show notes & episode transcript)

10 Steps to Improve Investing Success - free download

What to Do When the Stock Market Gets Crazy - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Connect With Us:

YouTube: Subscribe and join the conversation in the comments

Podcast apps: subscribe or follow YMYW in your favorite

Apple Podcasts: leave your honest reviews and ratings

Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:57 - Can I Afford to Be My Parents' Retirement Plan? (Daniel, Texas)

07:07 - Will an Annuity Really Save Mom From Running Out of Money? (Jemma)

15:07 - Can We Retire in Our Early 50s With a Pension and a $190K Spend? (Cookie and Gerry)

30:39 - Can We Retire Early at 46 With a $4M ESOP and a $210K Spend? (Fred and Wilma, CA)

44:23 - Outro: Next Week on the YMYW Podcast

Retirement Changes at These 5 Major Financial Crossroads - 569 Feb 17, 2026

When you're standing at a major financial crossroads, the timing of your decisions can mean the difference between success and failure. Joe Anderson, CFP® and Big Al Clopine, CPA spitball on the "when" of five retirement decisions, today on Your Money, Your Wealth podcast number 569. We'll kick things off with a whale of an email: "Fine and Dandy" is 42 years old with a multimillion dollar private equity offer on the table. Should he sell his business now or hold out for a second bite of the apple later? He also wonders if it's crazy to spend more on his vacation home than on his primary residence. David calls himself an "elderly orphan," flying solo at 66 and in need of a plan to protect his million-dollar portfolio as he ages. BB and Shell are trying to time their final year of retirement contributions to save as much as possible before moving to a lower-tax state. Should they go Roth IRA or traditional? Joel wonders when to take required minimum distributions from retirement accounts for the maximum tax benefit, and Brian in New York needs a spitball on when it makes sense to have an emergency fund as a retiree, and for how much.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-569 (full show notes & episode transcript)

Growing Your Wealth Guide - free download

Retirement Readiness Guide - free download

Retire at 62: Great Idea or Huge Mistake? - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:09 - Should I Sell My Business or Wait? Is It Crazy to Spend More on My Vacation Home Than My Primary Residence? (Fine and Dandy, IL)

20:48 - Saving to Roth IRA vs Traditional IRA in the Final Year Before Retirement (BB and Shell)

23:50 - When to Take Your First RMD for the Maximum Tax Benefit (Joel, CA)

27:33 - Aging Alone in Retirement: How to Protect Assets Before Cognitive Decline (David, 68, Logan, NM)

35:37 - Why Some CPAs Cap Roth Conversions at $500K AGI (Shweta, CA)

37:05 - When Does It Make Sense for Retirees to Have an Emergency Fund - and How Much? (Brian, Albany, NY)

42:03 - Outro - Next Week on the YMYW Podcast

Tax-Smart Investing at Every Age: Starting Young or Catching Up - 568 Feb 10, 2026

John Q. Taxpayer is in the home stretch of his career, looking for the best way to catch-up and build his tax-free bucket. Meanwhile, a pair of young financial nerds in Omaha are already strong savers, but they're wondering whether a simple "VOO for life" strategy is enough to help them reach multimillionaire status in retirement. Also, Janine retired unexpectedly. Can her remaining savings support a European retirement lifestyle? From Jonas Grumby's "glitch in the matrix" tax strategy to the potential tax nightmare of Dolly's literal sack of inherited gold coins, today on Your Money, Your Wealth® podcast 568, Joe Anderson, CFP® and Big Al Clopine, CPA. spitball on how folks from different generations with different situations can reach the same ultimate goal: positioning assets today to ensure the most tax-free wealth tomorrow. Plus, the fellas spitball on the "double taxation" trap of retirement plan loans for Pete in North Carolina, and the affordability of 50-year mortgages for Semper Fi in Michigan.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-568 (full show notes & episode transcript)

Why Asset Location Matters - free guide

All About Asset Location - more free resources

15 Maneuvers to Duck an Unplanned Early Retirement Knockout - YMYW TV

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:05 - After-Tax 401(k) Catch-Ups vs Taxable Investing (John Q Taxpayer)

06:16 - Forced Early Retirement: Social Security and Roth Conversion Timing? (Janine, Bothell, WA)

11:30 - Are 50-Year Mortgages Actually Affordable? (Semper Fi, Stevensville, MI)

17:59 - 401(k) Loan vs Mortgage Payoff (Pete, NC)

21:27 - Can You Manufacture a Step-Up in Basis? (Jonas Grumby, The Colony, TX)

25:03 - Inherited Gold Coins and Capital Gains Taxes (Dolly, 63, TN)

29:35 - Spitball for Young Investors Who Don't Have Millions (Young Financial Nerds, Omaha, NE)

42:13 - Outro: Next Week on the YMYW Podcast

Rising Costs and Retirement Unknowns? Here's What to Do - 567 Feb 03, 2026

Should Al and Peggy in Illinois keep hammering pre-tax retirement savings or should they pivot to post-tax Roth for better tax diversification? Which pension option is best for their early retirement plans? Long-term care insurance premiums are going up endlessly for Eloise in Connecticut. Is she walking into an insurance industry trap? How do Eric and Tami in Baton Rouge help their kids with college without blowing up their own retirement, and when do student loans make sense? Finally, should Lana and Sterling harvest capital gains or prioritize Roth conversions before moving to a much higher-tax state? The basic question in all of these is the same: how do you protect your future from rising costs and unknowns that are out of your control? We'll find out what it takes, today on Your Money, Your Wealth podcast number 567.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-567 (full show notes & episode transcript)

Key Financial Data Guide - free download

Retirement Panic Button: 7 Ways to Avoid Hitting It - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:55 - Pre-Tax vs. Late Roth Savings? Pension Lump Sum vs. Lifetime Income in Early Retirement? (Al & Peggy, Illinois)

14:14 - Should I Drop Long-Term Care Insurance Now at Age 70? (Eloise, Connecticut)

20:41 - College Costs vs Retirement Security for Parents (Tami & Eric, Baton Rouge, LA)

35:59 - Roth Conversions or Capital Gains Before Moving to a High Tax State? (Lana & Sterling, Nebraska)

48:14 - Next Week on the YMYW Podcast

High Net Worth Pre-Retirees Share Their Biggest Fear (Here's How to Calm It) - 566 Jan 27, 2026

"Mr and Mrs Smith" have nearly $850,000 saved at age 43, but they're very concerned about retirement. "Lucy and Desi" are 58 and 64 with nearly $7 million saved, but they still lie awake wondering if it's enough for their high-expense life. "Tony and Carmela" are in a similar boat with millions saved at 61 and 59, but they're worried their asset allocation won't get them through their retirement. No matter the numbers, the fears sound exactly the same: will you run out of money in retirement? Turns out overcoming that fear is not about hitting a magic number. We'll find out what it's all about today on Your Money, Your Wealth podcast number 566 with Joe Anderson, CFP®, and Big Al Clopine, CPA. The fellas also spitball Roth conversions, long/short direct indexing capital gains tax strategies for "Juicy Squeeze", working after retirement for Wendi, and how one confusing word can completely change a retirement timing decision for "Jacques and Johana."

Free Financial Resources in This Episode:

https://bit.ly/ymyw-566 (full show notes & episode transcript)

Withdrawal Strategy Guide - free download

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

WATCH 6 Signs You Truly Have "Enough" For Retirement on YMYW TV

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:01 - 43 With $850K. Am I Too Late to Build Enough Roth Money? (Mr & Mrs Smith, Dallas, TX)

11:29 - Nearly $7M Saved at 58 and 64. Do We Have Enough for a High-Spend Retirement? (Lucy & Desi, Jersey Shore, NJ)

23:38 - 61 and 59 With $4.5M Saved. Can I Retire Now With a 50/50 Portfolio? (Tony & Carmela, San Ramon, CA)

32:09 - Mid-50s with $685K Saved. Can One Spouse Retire While the Other Works? (Jacques & Johana, Florida)

38:53 - Are Long-Short Direct Indexing Tax Strategies Worth the Fees? (Juicy Squeeze)

47:04 - Should I Work as an Employee or Contractor After 70 on Social Security? (Wendi)

52:04 - Outro: Next Week on the YMYW Podcast

48 and Worried About Early Retirement? This Changes the Math - 565 Jan 20, 2026

Lucky Lou is 48, burned out and wants to punch at 50. How should he bridge the gap before pensions and Social Security? Joe Anderson, CFP®, and Big Al Clopine, CPA walk through the Rule of 55, 72(t)s, and the psychological reality of spending down a taxable account, today on Your Money, Your Wealth® podcast number 565. Alexei and Anna are high earners in their mid-20s who want to save aggressively and keep taxes low. Which retirement accounts should they prioritize, and can they afford a downpayment on a house? Jay and Gloria are wrestling with the classic question of whether to save to Roth or traditional 401(k), especially since their state doesn't tax retirement income. Is taking the deduction now and backdooring Roths the smarter move? Plus, Sleepless in Seattle wants to know, can her 28-year-old daughter afford to buy a condo in a high-cost housing market? Finally, Jennifer in Texas wonders how to invest and withdraw an inherited IRA over the 10-year rule with the least tax damage.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-565 (full show notes & episode transcript)

The Last 5 Years Before Retirement Will Decide Your Lifestyle - Here's How - YMYW TV

Guides:

Blogs:

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:04 - Can I Retire at 50 with $5M and Bridge the Gap to Pensions and Social Security? (Lucky Lou)

10:51 - Which Retirement Accounts Should Young High Earners Max First? Can We Afford a House Downpayment? (Alexei & Anna, Cincinnati)

17:57 - Save to Roth 401(k) or Traditional If Our State Doesn't Tax Retirement Income? (Jay & Gloria, People's Republic of IL)

28:21 - Should a 28-Year-Old Buy a Home in an Expensive Market? (Sleepless in Seattle)

37:15 - How to Invest for Most Growth and Least Tax on an Inherited IRA? (Jennifer, TX)

41:04 - Outro: Next Week on the YMYW Podcast

Social Security Timing and When Family Wrecks Retirement - 564 Jan 13, 2026

Hana's mom is 92. Mom's husband is 74, and after years of trying to help a family member, nearly a million dollars is gone. How do they stop the bleeding before it's too late, and how much can they spend each year from what's left? That's today on Your Money, Your Wealth® podcast number 564 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, "Peter and Gwen" from Virginia have a pension, Roths, and a shrinking IRA. With the new tax law, IRMAA, and Social Security decisions all colliding, should they keep converting to Roth, and when should they actually collect Social Security? Also, does it make sense for "Mr. and Mrs. Scarecrow" to claim Social Security early and invest it? Finally, "Rosie and Astro" from Pennsylvania ask if they can retire in just three years with $1.3 million, and whether it's time to hire an advisor to help them get there.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-564 (full show notes & episode transcript)

Social Security Handbook

Retirement Readiness Guide

6 Biggest Financial Pitfalls in America (Avoid These Traps!) - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

02:21 - Family Wrecking Retirement: How Much Can Benevolent Retirees Afford to Spend? (Hana)

10:30 - We Have a Pension. Should We Do Roth Conversions After the OBBBA? When to Claim Social Security? (Peter Parker & Gwen Stacy)

23:29 - Should We Claim Social Security Early and Invest It? (Mr & Mrs Scarecrow)

29:56 - We're 60 and 57 with $1.3M. Can We Retire in 3 Years? Should We Hire an Advisor? (Rosie & Astro, PA)

41:04 - Outro: Next Week on the YMYW Podcast

How to Beat the "Fire Hydrant" of Future Taxes: YMYW Best of 2025 - 563 Jan 06, 2026

YMYW friends, welcome to 2026. What actually mattered most to you in 2025? It turns out to be tax-free gains on investments, retirement timing, and claiming Social Security. Today on Your Money, Your Wealth® podcast number 563, Joe Anderson, CFP® and Big Al Clopine, CPA break down the smartest tax moves, the biggest Roth mistakes to avoid, and how real people solve real retirement problems - with the help of special guests Susan Brandeis CFP® and the IRA guru, Ed Slott, CPA. Find out when Roth conversions help or hurt, how to lower lifetime taxes for you and your heirs, what it really takes to retire confidently, even without a massive portfolio, and more. Watch or listen and steal the financial strategies that made YMYW's most popular episodes of the year.

Free Financial Tools & Resources in This Episode:

https://bit.ly/ymyw-563 (full show notes & episode transcript)

The Complete Roth Papers Package - 3 free downloads in one!

Don't Let These 10 Risks Break Your Retirement - YMYW TV

Financial Blueprint (self-guided)

EASIRetirement (self-guided)

Financial Assessment (Meet with an experienced professional)

LISTEN to the Best of the YMYW Podcast 2021, 2022, 2023, 2024

LISTEN to the Top Funniest Moments from the YMYW Podcast Vol. 1, Vol. 2

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast
00:54 - Roth IRA is "The Greatest Account Ever" Per Ed Slott. But Why?

from ep. 526: YMYW most listeners and plays in 2025 on Apple Podcasts, YMYW most downloaded in 2025 across all podcast platforms

20:46 - Is There a Point Where Roth Conversions No Longer Make Sense? (Jerry, Phoenix, AZ)

from ep. 535: YMYW most views, watch time, and new subscribers in 2025 on YouTube, most engaged listeners in 2025 on Apple Podcasts

32:13 - Roth Conversions vs. Taking Advantage of Zero Percent Cap Gains (Skipper, CA)

from ep. 517: YMYW most consumed episode in 2025 on Apple Podcasts

43:06 - We're in Our Early 40s with $795K Saved. Can We Retire at 55? (Mr Buckeye, OH)

from ep. 546: YMYW longest average view duration in 2025 on YouTube

55:12 - Is My Husband Eligible for Spousal Social Security Benefits Now that WEP and GPO Are Gone? (Cherilyn, El Cajon, CA)

from ep. 536: YMYW most plays, most listeners, and most viewers in 2025 on Spotify

59:53 - Outro: 2025 Stats and Next Week on the YMYW Podcast

I'm 42 and Burned Out with $2.25M. Can I Retire Early from My Toxic Job? - 562 Dec 30, 2025

Today on Your Money, Your Wealth podcast 562 (an encore of episode 513), Joe Anderson, CFP® and Big Al Clopine, CPA spitball for YMYW listeners in their 40s who are ready to call it quits at work, become financially independent, and retire early. Can they afford to do it? Peter and Joanna want to retire in the next two years. Burned Out and Ready to Retire wants out of his toxic office. If Maryland Chicken Man never earns another dollar, how much can he afford to withdraw from his retirement accounts each year? And Suzanne in Massachusetts is 69 and needs $60K a year for the next 30 years. Is she all right?

(While Joe and Big Al enjoy a little seasonal downtime and Andi recovers from surgery, enjoy this encore presentation of these questions from an early 2025 episode.)

Free Financial Resources in This Episode:

https://bit.ly/ymyw-562 (full show notes & episode transcript)

2025 Key Financial Data Guide - free download

10 Big Retirement Regrets to Avoid (Before It's Too Late) - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast 01:30 - We're 45 and 44. Can We Retire in the Next 2 Years? (Peter & Joanna, NJ) 10:45 - Watch 10 Big Retirement Regrets to Avoid (Before It's Too Late) on YMYW TV, Calculate your Free Financial Blueprint 11:44 - I'm 42 and I Work in a Toxic Office. Can I Afford to Retire? (Burned Out and Ready to Retire, NJ) 21:53 - Download the 2025 Key Financial Data Guide for free 22:53 - I'm 69 and Need $60k/Year for the Next 30 Years. Am I All Right? (Suzanne, MA) 25:40 - I'm 45. If I Never Earn Another Dollar How Much Can I Withdraw Every Year? (Maryland Chicken Man) 35:15 - Outro: Next Week on the YMYW Podcast

Retirement Finances Whether You're Married, Separated, or Single - 561 Dec 23, 2025

Financially speaking, should Old Bear in Northern Kentucky marry his Honey? How should Sebastian in Virginia navigate the financial aspects of his separation? Plus, Famous Missourians want to know, how much is enough for retirement and when can you take your foot off the gas? Can Paul with the Big Wallet Bridge the long gap between retiring and claiming Social Security benefits? And can Aspiring Adventurer in Oregon retire single at age 58?

(While Joe and Big Al enjoy a little seasonal downtime and Andi recovers from surgery, enjoy this encore presentation of these questions from an early 2025 episode.)

Free Financial Resources in This Episode:

https://bit.ly/ymyw-561 (full show notes & episode transcript)

DOWNLOAD The Going Solo Guide for free

WATCH: Going Solo: Navigating Your Financial Future Single on YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:01 - Financially Speaking, Should Old Bear Marry His Honey? (Northern Kentucky, near Cincinnati, OH)

08:41 - Navigating Finances When Separating from Your Spouse (Sebastian, VA)

15:13 - Watch Going Solo: Navigating Your Financial Future Single on YMYW TV, Download the Going Solo Guide for free

15:42 - How Much is Enough for Retirement? When Can We Take Our Foot Off the Gas? (JC Penney & Laura Ingalls Wilder, Kansas City, MO)

28:31 - How to Bridge the Long Gap Between Retirement and Social Security (Paul with the Big Wallet)

38:50 - Calculate your free Financial Blueprint

39:20 - Can I Retire at Age 58? Where to Save? Should I Do a Roth Conversion Ladder in Retirement? (Aspiring Adventurer, OR)

51:00 - YMYW Podcast Outro

The Truth About High Income Investments and Retirement Safety - 560 Dec 16, 2025

Today on Your Money, Your Wealth® podcast 560, Joe Anderson, CFP® and Big Al Clopine, CPA spitball business development company (BDC) funds for Edward in Illinois before diving into buckets of cash, T-bills, decumulation, and Roth conversion timing for Pebbles and Bam Bam. Plus, the fellas help 34 year old Keith in Connecticut figure out if he's actually on track, whether he's taking too much risk, or just worrying too much. They also spitball on the six-figure annuity gain that Gus in Philly's 95 year old dad has amassed. Finally, why yelling "never pay an advisor" on the internet doesn't necessarily magically turn MYGAs into the perfect investment for everyone.

(While Joe and Big Al enjoy a little seasonal downtime and Andi recovers from surgery, enjoy this encore presentation of these questions from a January 2025 episode.)

Free Financial Resources in This Episode:

https://bit.ly/ymyw-560 (full show notes & episode transcript)

10 Steps to Improve Investing Success - free download

Tax-Smart Charitable Giving Guide

6 Secrets to Bigger Tax Deductions from Your Non-Profit Donations - YMYW TV

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Chapters:

00:00 - Intro: This week on the YMYW Podcast

01:03 - What's the Risk With Business Company Development (BDC) Funds? (Edward, IL)

03:58 - T-Bills, Decumulation, IRAs, and Investing Strategies (Pebbles & Bam Bam, Kentuckystone)

12:02 - I'm 34. Are My Investments Appropriate for My Time Horizon? (Keith, CT)

17:59 - MYGA Retirement Withdrawal Strategy for Dad (Gus in Philly)

23:00 - Just Buy Multi-Year Guaranteed Annuities (MYGAs) and Bonds (comment from Ken, YouTube)

28:04 - YouTube comments: State Taxes, Pro-Rated Sale of Primary Residence, Bonds vs. Pension, and PERMA

35:27 - YMYW Podcast Outro

Will Buying Your Dream Home Ruin Early Retirement? - 559 Dec 09, 2025

Today on Your Money, Your Wealth® podcast 559 with Joe Anderson, CFP®, and Big Al Clopine, CPA, David wants to know if he and his wife (ages 47 and 53) are actually on track for retirement - without realizing they're creeping toward that .01% crowd that David swears he is not part of. Mia and Jessie from Seattle want to retire and still pick up a dream lake house with a combined ten million dollars saved. Can they pull it off? Yosemite Sam from Allen, Texas, wonders if he should wipe out the lake house mortgage or keep that low-rate loan to hang on to more flexibility as he approaches retirement. Joe and Big Al also spitball on whether Todd and Margo should shift more into pre-tax accounts to leave their corporate jobs at age 50, and whether early retirement at 55 plus a $500,000 beach home is in the cards for Birdie and Bogey from Williamsburg.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-559 (full show notes & episode transcript)

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:53 - Middle Class Retirement Spitball For Those Not in the .01%: Are We On Track at Age 47? (David)

06:37 - $5 Million Roth, $5 Million Brokerage: Can We Retire and Buy a Dream Lake House? (Mia & Jessie, Seattle)

17:26 - Pay Off the Lake House or Keep the Low Rate Mortgage? (Yosemite Sam, Allen, TX)

25:23 - Should We Shift More Funds into Pre-Tax Retirement to Retire Early at 50? (Todd & Margo, TX)

38:45 - Can We Afford Early Retirement at 55 and a $500K Beach Home? (Birdie & Bogie, Williamsburg, VA)

46:27 - Outro: Next Week on the YMYW Podcast

Roth IRA vs. Traditional IRA: Which is Better for Retirement Savings? - 558 Dec 02, 2025

McDreamy Dempsey wants to know if converting to Roth in the 37% tax bracket ever makes sense, and Gary in La Crosse warns Joe Anderson, CFP® and Big Al Clopine, CPA about Roth conversion "lag" and when it DOESN'T make sense to convert, today on Your Money, Your Wealth® podcast 558. Plus, Wine Guy and Gal in Northern California want a spitball on whether they should protect their ACA subsidies or keep converting to Roth before Medicare kicks in. Then it's the classic question for Robert in Napa, Luke and Lorelai in Indiana, and Phil and Claire in California: should they save for retirement in their traditional, pre-tax, tax-deferred accounts, or their post-tax, tax-free Roth accounts? Different needs and situations, same big question: which strategy gives you the smarter tax outcome?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-558 (full show notes & episode transcript)

Top 10 Tax Tips Guide - limited time special offer, download yours before Friday, Dec 5, 2025!

Ultimate Guide to Roth IRAs - free download

2025 Key Financial Data Guide - free download

10 Tax-Cutting Moves to Make Now - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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Chapters:

00:00 - Intro: This week on the YMYW Podcast

00:57 - Should High Earners Do Roth Conversions in the 37 Percent Bracket? (McDreamy Dempsey)

06:50 - The Hidden Roth Conversion Lag: When Conversions Don't Actually Pay Off (Gary, LaCrosse, WI)

18:03 - Should You Prioritize the ACA Subsidy Cliff or Roth Conversions Before Medicare? (Wine Guy & Gal, No CA)

26:27 - Traditional vs Roth Contributions: What's Better When You Make $400K? (Robert, Napa)

33:09 - Roth or Traditional Contributions? Save More or Coast After Debt Payoff? (Luke & Lorelai, Indiana)

42:13 - Roth or Traditional at Age 48: Which Strategy Makes More Sense? (Phil & Claire, CA)

49:19 - Outro: Next Week on the YMYW Podcast

UGMA, 529, HSA, RMD, and Inherited IRA Tax Bombs Defused - 557 Nov 25, 2025

Joe Anderson, CFP® and Big Al Clopine, CPA are defusing some confusing tax time bombs today on Your Money, Your Wealth® podcast number 557. George in Torrance wants to know the smartest way to deal with the giant UGMA account set up by his kids' grandparents. Suzanne in Detroit has a twist on the new 529 plan to Roth rollover rule. Homer and Marge need a spitball on whether they can build huge 529 plans for college savings and still retire early. Plus, Bill in Chicago just inherited a $950K IRA and needs a withdrawal plan before he triggers a tax explosion. Aaron in Cincinnati wonders whether maxing out his health savings account every year as part of his overall pre-tax contributions is a good idea. Carl in Western Maryland has questions about the required minimum distribution age and HSA rules, and wonders whether those who make the tax code are on drugs. And finally, Marc wants to know how to avoid the tax kaboom from $the 4M sitting in his traditional IRAs at age 73.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-557 (full show notes & episode transcript)

DIY Retirement Guide - limited time Special Offer, download yours by Friday November 28, 2025!

Financial Advisors Expose the Internet's Worst Retirement Strategies! - YMYW TV

Financial Blueprint (self-guided)

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Chapters:

00:00 - Intro: This week on the YMYW Podcast

01:07 - Best Tax Moves When Your Kid Has a Huge UGMA Account (George, Torrance, CA)

06:23 - 529 to Roth Rollover or Save for Grad School: What's the Smarter Play? (Suzanne, Detroit)

14:47 - Can $650K High Earners Afford to Build Huge 529 Plans and Still Retire Early? (Homer and Marge, No CA)

24:01 - Inherited IRA Withdrawal Plan: How Much Should You Take Out Annually? (Bill, Chicago)

31:23 - Should You Really Max Out Your HSA Every Year? (Aaron, Cincinnati, OH)

33:07 - Do You Take RMDs at 73 or 75? Was the Government on Drugs When They Came Up with HSA Rules? (Carl, Western MD)

38:07 - 73 With $4 Million in IRAs: What's the Best Tax Strategy? (Marc, 92024 - Encinitas, CA)

39:31 - Outro: Next Week on the YMYW Podcast

Roth Conversions vs. 0% Capital Gains Rate: a Retirement Tax Trap? - 556 Nov 18, 2025

Joe Anderson, CFP® and Big Al Clopine, CPA spitball Roth conversions, capital gains, and retirement readiness from every angle, today on Your Money, Your Wealth® podcast number 556. Joe Momma from Virginia wants to know if his zero percent capital-gains strategy is too good to be true, if he can trust his advisor, and if it's finally time to start converting to Roth. David in Poway is already converting his IRA to Roth, but should they convert his wife Shannon's too? Thomas wonders when in retirement to finally start using the Roth money he's saved, instead of just admiring it. And Lizzy and Billy from Texas want to know if $3.5 million is enough for them to retire in 7 years at ages 62 and 65.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-556 (full show notes & episode transcript)

2025 Tax Planning Guide - free download

Escape These 11 Tax Traps and You'll Save in Retirement - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:46 - Keep 0% Capital Gains or Convert to Roth? Should I Trust My Advisor? (Joe Momma, VA)

12:03 - I'm Converting My IRA to Roth. Should We Convert My Wife's IRA Too? (David & Shannon, Poway, CA)

17:39 - How to Use Roth IRA Money in Retirement (Thomas)

25:34 - Can We Retire at in 7 Years at 62 and 65 on $3.5M? (Lizzy and Billy, TX)

29:33 - Outro: Next Week on the YMYYW Podcast

Retiring Before Social Security? Consider These Portfolio Changes - 555 Nov 11, 2025

Joe Anderson, CFP® and Big Al Clopine, CPA spitball withdrawal strategies, Roth conversion timing, and saving priorities for every stage of life, today on Your Money, Your Wealth® podcast number 555. Christine just retired at 59 and wants the smartest way to draw income before Social Security, without letting taxes take a third of it. Prickly Richard and Margarita Maggie have a plan to "pull ahead" some Roth conversions now to dodge an RMD avalanche later. Will it work? And the Michigan Queen and Mississippi Boy are wondering whether to save harder for retirement or college for three kids currently under the age of 5.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-555 (full show notes & episode transcript)

Tax-Free Retirement Guide - NEW! Free download

How To Retire Tax-Free With A Smart Income Plan on YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

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Connect With Us:

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Apple Podcasts: leave your honest reviews and ratings

Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:53 - I Retired at 59. What's My Best Retirement Withdrawal Strategy Before Social Security at 62? (Christine)

13:50 - Should We Do Roth Conversions Before Being Hit With the RMD Avalanche? (Prickly Richard & Margarita Maggie, Tucson, AZ)

26:20 - Saving for Early Retirement at 55 vs. Saving for Kids' Future (Michigan Queen & Mississippi Boy, TN)

39:53 - Outro: Next Week on the YMYW Podcast

Change of Roth Plans for the New Senior Tax Bonus? Tax-Loss Wins? - 554 Nov 04, 2025

Should the new temporary senior tax deduction change your Roth conversion strategy? Joe and Big Al spitball for Chris in Maple Grove, Minnesota, who wonders whether to keep converting to Roth now that the $6,000 Senior Bonus deduction phases out with higher income, today on Your Money, Your Wealth® podcast 554 with Joe Anderson, CFP®, and Big Al Clopine, CPA. Teri from Salt Lake City's broker has amassed $60,000 of losses in Teri's $1.1 million account due to tax-loss harvesting. When is enough… enough? Windy Chicago in Chino Hills, California, wonders what to do about their cost basis vanishing after transferring mutual funds to Vanguard, and Larry and Sally from Michigan are planning for retirement while facing significant health challenges. Can they afford to bridge the healthcare gap and still retire safely?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-554 (full show notes & episode transcript)

One Big Beautiful Bill Act Guide

Retirement Income Strategies Guide

Retirement Rebound: 5 Plays to Help You Score a Comeback - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

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Connect With Us:

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Apple Podcasts: leave your honest reviews and ratings

Chapters:

00:00:00 - Intro

00:00:56 - Should We Stop Roth Conversions for the New $6,000 Senior Bonus Tax Deduction? (Chris, Maple Grove, MN)

00:07:44 - Lost Cost Basis After Moving Funds to Vanguard. Now What? (Windy Chicago, Chino Hills, CA)

00:10:21 - Tax Loss Harvesting: When Is It Too Much? (Teri, Salt Lake City)

00:18:49 - Can We Retire with Rising Health Costs and Care Needs? (Larry & Sally Morgan, voice)

00:33:34 - Outro: Next Week on the YMYW Podcast

Should You Convert to Roth Before or After You Retire? - 553 Oct 28, 2025

Joe Anderson, CFP® and Big Al Clopine, CPA tackle one of the trickiest timing questions in retirement planning, today on Your Money, Your Wealth podcast number 553: when should you convert to Roth, while you're still earning, or after retirement? First, James from Texas wonders if it's worth maxing out his high-fee 457 plan, or if he's better off investing in a low-cost brokerage account. Full-time travelers "Lois and Clark" want to know how much they should keep converting to Roth now that they're on Medicare. Ray Charles in Chicago is burned out on corporate life and plans to quit at 55. Is that the perfect time for him to start Roth conversions? And finally, Gun and Rose from Louisiana ask if borrowing again from their 401(k) is a smart move.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-553 (full show notes & episode transcript)

Retirement Lifestyles Guide - free download

Ultimate Guide to Roth IRAs - free download

Will Your Money Last Through Retirement? - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

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Connect With Us:

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Podcast apps: subscribe or follow YMYW in your favorite

Apple Podcasts: leave your honest reviews and ratings

Chapters:

00:00:00 - Intro: This Week on the YMYW Podcast

00:00:56 - 457(b) vs. Brokerage: Are High Fees Worth the Tax Break? (James, TX)

00:06:43 - Roth Conversions in Retirement: Hitting the Road and the 12% Bracket ("Lois & Clark", FL)

00:19:54 - Early Retirement Pivot: Quit at 55 and Convert to Roth? ("Ray Charles", Chicago, IL)

00:33:28 - Should We Borrow From 401(k) For Home Repairs? (Gun & Rose, LA)

00:38:54 - Outro: Next Week on the YMYW Podcast

Don't Let Money Anxiety Ruin Your Retirement - 552 Oct 21, 2025

Joe Anderson, CFP® and Big Al Clopine, CPA tackle the fears that mess with even the best-laid financial plans, today on Your Money, Your Wealth® podcast 552. Big Wallet Barbie and Ken from the Midwest have saved millions, but Barbie's still worried about retiring early, buying a new house, and converting to Roth. Is she second-guessing her plans? The fellas spitball for Dan from Florida, who's flying high in the 35% tax bracket and trying to decide between Roth 401(k) contributions and future Roth conversions. They also float a surprising idea - one that's rare on YMYW - for a listener from Chicago who is FIRE'd Up about Roth vs. pre-tax and making a tax-smart wealth transfer. We'll wrap up with a couple of your comments.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-552 (full show notes & episode transcript)

Emotionless Investing Guide

The Truth About Your Love/Hate Relationship With Money - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

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Connect With Us:

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Apple Podcasts: leave your honest reviews and ratings

Chapters:

00:00:00 - Intro: This Week on the YMYW Podcast

00:00:49 - Big Wallet Barbie and Ken's Roth Conversion, Retirement, and Home Purchase Strategy (Barbie Mattel, Midwest)

00:08:58 - Roth 401(k) Contributions or Roth Conversions? Flying High in the 35% Tax Bracket (Dan, FL)

00:17:23 - High-Earners Planning FIRE and Wealth Transfer: Roth, Pre-Tax… Life Insurance? (FIRE'd Up, Chicago)

00:29:56 - Correction on Spousal Social Security Benefits After the Fairness Act (Cindy)

00:33:37 - Follow Up: The Kids Are Pretty Alright (Lucas, MN)

00:34:44 - Outro: Next Week on the YMYW Podcast

Where Should You Take Retirement Money First If You've Saved $2M? - 551 Oct 14, 2025

We're playing "which comes first" today on Your Money, Your Wealth® podcast number 551 with Joe Anderson, CFP® and Big Al Clopine, CPA. "Retired G-Man and Nurse Ratched" from Pennsylvania have saved $2 million. Should they withdraw money first from their IRA or their taxable accounts in retirement? "Mike and Carol in Florida" want to know when and how much to convert to Roth, but they're also sitting on a mountain of company stock. Should they deal with that first? Mackey in Florida is 55 and wonders if he can retire now with $2.6 million and some lingering debt - but there's an important first he's missing too! Plus, Mike in Utah asks Joe and Big Al to spitball on a plan for his 90-year-old mom's $1.9 million annuity, and Doc McMuffin in Minnesota asks for the fellas' take on her plan to gift appreciated assets to her parents.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-551 (full show notes & episode transcript)

YourMoneyYourWealth.com - all our financial resources! Ask Joe and Big Al, blogs, workshops, financial guides, and 11 seasons of YMYW TV!

10 Big Retirement Regrets to Avoid (Before It's Too Late) - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

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READ financial blogs

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Connect With Us:

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Apple Podcasts: leave your honest reviews and ratings

Chapters:

00:00:00 - Intro: This Week on the YMYW Podcast

00:00:53 - How to Retire at 55 With $2.6M and Debt? First, How to Write a Good Spitball Request (Mackey, FL)

00:03:46 - Sequence of Retirement Withdrawals: IRA First or Taxable First? (G-Man and Nurse Ratched, PA)

00:12:10 - Roth Conversions vs Concentrated Stock: Which Comes First? (Mike & Carol, FL)

00:29:27 - What to Do With 90-Year-Old Mom's $1.9M Annuity? (Mike, UT)

00:40:59 - Is Gifting Appreciated Assets to Parents Tax-Smart or Risky? (Doc McMuffin, MN)

00:48:27 - Outro: Next Week on the YMYW Podcast

Is Your Roth Conversion Timing All Wrong? (Financial Blunders) - 550 Oct 07, 2025

Joe and Big Al spitball on how to avoid screwing up the timing of your Roth conversions, today on Your Money, Your Wealth® podcast number 550. Barrie from New York is 62 and single, and she's been diligently converting pre-tax money each year for lifetime tax-free Roth growth. Should she continue after she retires next year? "Jerry and Elaine" want to retire in the next six years and still leave the kids an inheritance. When should they start Roth conversions? Alex in Pennsylvania is a 31-year-old software engineer. Should he convert his IRA to Roth all at once? Plus, how can he transition into a career as a financial planner? A clarification on the age plus 20 rule of thumb for retirement contributions from one of our YouTube viewers is very un-clarified for Joe, and the fellas let Lisa in San Diego know whether she can use her rental real estate income to fund a Roth 401(k).

Free Financial Resources in This Episode:

https://bit.ly/ymyw-550 (full show notes & episode transcript)

Ultimate Guide to Roth IRAs

6 Signs You Truly Have "Enough" for Retirement - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

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Connect With Us:

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Podcast apps: subscribe or follow YMYW in your favorite

Apple Podcasts: leave your honest reviews and ratings

Chapters:

00:00:00 - Intro: This Week on the YMYW Podcast

00:00:55 - Should I Keep Converting $20K a Year in Retirement? (Barrie, NY)

00:07:17 - Can We Retire at 62 and Still Leave an Inheritance? Roth Conversion Strategies for Big Accounts (Jerry & Elaine, KS)

00:17:05 - I'm 31. Should I Convert $57K Now or Spread It Out? (Alex, PA)

00:29:12 - Roth Conversion Timing Before Retirement (Mike, Philly Suburbs)

00:36:49 - Confused About Roth Withdrawal Rules at 60 (Lisa, Omaha NE)

00:40:05 - Clarification on the Age + 20 Rule of Thumb for Contributions (Matt, YouTube)

00:45:40 - Can Rental Property Income Fund a Roth 401(k)? (Lisa, San Diego)

00:47:24 - Outro: Next Week on the YMYW Podcast

Can You Retire on $6 Million? Here's What It Looks Like - 549 Sep 30, 2025

Today on Your Money, Your Wealth® podcast number 549 with Joe Anderson, CFP® and Big Al Clopine, CPA, a comment on one of our YouTube videos sparks a dialogue between Joe and Big Al on the 4% rule vs. the "guardrails" withdrawal strategy. Joe at the Beach is managing his ~$6M portfolio on his own, but wants the fellas' take on his upper limit for yearly spending, so he can keep drinking his old-fashioneds. Can Joe Ko in Virginia afford to bridge the gap between retiring at 67 and taking Social Security at 70? Plus, "Harold and Maude" have nearly $7M saved. Should they accelerate Roth conversions into high-tax brackets before moving from low-tax Colorado to high-tax California? And how much more than their current annual spend can they afford for family vacations and travel?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-549 (full show notes & episode transcript)

Withdrawal Strategy Guide

Cruising Into Retirement Checklist and Guide (limited time offer, download by this Friday!)

How to Cruise Into Your Retirement - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

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Connect With Us:

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Podcast apps: subscribe or follow YMYW in your favorite

Apple Podcasts: leave your honest reviews and ratings

Chapters:

00:00:00 - Intro: This Week on the YMYW Podcast

00:00:50 - What About the Guardrails Withdrawal Strategy? (Bill, YouTube)

00:04:13 - I'm 69 with $5.7 Million Saved. What's the Max I Can Spend in Retirement? (Joe at the Beach)

00:15:12 - 63 and 58 With $1.85M Saved. How Much Can We Spend from 67 Until Social Security at 70? (Joe Ko, VA)

00:21:30 - We're 61 and 69 with $7.6 million. Can We Increase Our Retirement Spending? How Should We Do Roth Conversions? ("Harold and Maude", Durango, CO)

00:33:49 - Outro: Next Week on the YMYW Podcast

Is Financial Software Giving You False Retirement Confidence? - 548 Sep 23, 2025

Wendy and Joe in Colorado ran the numbers, and their financial planning software says they'll have over $10 million when they pass. Wendy's wondering if they should continue converting to Roth while working, despite their high tax bracket. But has the software lulled them into a false sense of security? That's today on Your Money, Your Wealth® podcast number 548 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, which is smarter for "Kurt and Courtney" in New York: aggressively paying down their mortgage, or putting their extra money to work in the market before Kurt retires early in 20 years? Finally, when does it stop making sense for high-earners "Tim and Faith" in Boston to contribute to their Roth? The fellas duke it out on this one (and we figure out, based on our earliest musical interests, which era we're each children of.)

Free Financial Resources in This Episode: https://bit.ly/ymyw-548 (full show notes & episode transcript)

Pay Off the Mortgage?

- YouTube playlist

- Spotify playlist

DOWNLOAD The Retirement Readiness Guide

WATCH 4 Hard Truths About Retirement You Need to Face on YMYW TV

Financial Blueprint (free, self-guided)

Financial Assessment (free, meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

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Connect With Us:

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Podcast apps: subscribe or follow YMYW in your favorite

Apple Podcasts: leave your honest reviews and ratings

Chapters:

00:00 - Intro: This Week on the YMYW Podcast 01:11 - Financial Software Says We'll Have $10M. Should We Continue Converting to Roth While Working, Despite Our High Tax Bracket? (Wendy, Loveland, CO) 16:35 - Watch 4 Hard Truths About Retirement You Need to Face on YMYW TV, Download the Retirement Readiness Guide 17:37 - What Are the Pros and Cons of Paying Off Our Home Before I Retire Early? (Kurt & Courtney, NY) 31:54 - Pay Off the Mortgage: YMYW Podcast Playlists on YouTube and Spotify, Calculate your free Financial Blueprint 32:51 - We're Late 40s With $3M + $2M RSUs. Continue Contributing to Tax-Deferred? Are We On Track for Retirement at 55 or 60? (Tim & Faith, MA) 46:15 - Next Week on the YMYW Podcast 46:37 - YMYW Podcast Outro

Roth Conversions: When to Make 'Em, When to Take 'Em - 547 Sep 16, 2025

A YMYW listener from Missouri and his wife are retired at 69 and 67, with less than $2 million dollars. Should they continue converting retirement savings to Roth for the tax-free growth? What should they do about long term care insurance? More importantly, is our listener's name (Cousy) pronounced "Cuzzy" or "Koozy"? Speaking of Roth conversions, must "Peggy Hill" wait five years to withdraw her conversion money, or only its earnings? That's today on Your Money, Your Wealth® podcast number 547 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, is Skipper's retirement payout plan the killer deal he thinks it is? How can Jeff in Dallas pay less capital gains tax on his 3 million dollar single stock, million dollar 401(k), and potential eBay income? Is selling on eBay still a thing? Does Dolly in Tennessee need to empty her inherited IRA within the next 10 years due to the SECURE Act? And finally, HSA vs. HRA: how should Larry in Rhode Island navigate switching from his current employer's health savings account to his future employer's health reimbursement arrangement?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-547 (full show notes & episode transcript)

5 Year Rules for Roth IRA Withdrawals

2025 Key Financial Data Guide (newly updated with One Big Beautiful Bill changes)

10 Steps to Improve Investing Success

What to Do When the Stock Market Gets Crazy - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Connect With Us:

YouTube: Subscribe and join the conversation in the comments

Podcast apps: subscribe or follow YMYW in your favorite

Apple Podcasts: leave your honest reviews and ratings

Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:11 - Should We Continue Roth Conversions in Retirement? What About Long-Term Care? (Cousy, MO)

13:03 - Must I Wait 5 Years to Withdraw My Roth Conversion, Or Only Its Earnings? ("Peggy Hill", MN)

21:50 - Is My Retirement Plan Payout the Killer Deal I Think It Is? (Skipper)

28:07 - How to Minimize My Capital Gains Tax? (Jeff, Dallas, TX)

33:37 - Must I Empty My Inherited IRA Within 10 Years With The SECURE Act? (Dolly, Bristol, TN)

37:50 - HSA and HRA: Health Savings Account vs. Health Reimbursement Arrangement (Larry, RI)

40:48 - Outro: Next Week on the YMYW Podcast

How to Accomplish Your Retirement Goals - Even Without a Fat Wallet - 546 Sep 09, 2025

We heard your feedback, and today on Your Money, Your Wealth® podcast number 546, Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing retirement for the not-so-fat wallets: Joe and Masako in Washington state and Reid in Indiana have less than a million saved. Can they still accomplish their retirement goals in their 60s? Mr Buckeye in Ohio and Old Macdonald in Maine have less than a million saved, and Curt in Pennsylvania has less than $1.5 million saved. Can they retire early - in their 40s and 50s?

Free financial resources & episode transcript: https://bit.ly/ymyw-546

DOWNLOAD The Going Solo Guide

WATCH Going Solo: Navigating Your Financial Future Single on YMYW TV

CALCULATE your free Financial Blueprint

SCHEDULE your Free Financial Assessment

ASK Joe & Big Al for your Retirement Spitball Analysis

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

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JOIN THE CONVERSATION on YouTube

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast 00:36 - We're 59 and 65 with Less than $1M. Can We Still Accomplish Our Retirement Goals? (Joe and Masako, WA state) 08:18 - We're 33 with $200K. Can We Retire at 65 and Spend $159K/Year? (Reid, IN) 15:58 - Calculate your Free Financial Blueprint 16:32 - We're Early 40s With $795K. Can We Retire at 55? (Mr Buckeye, OH) 28:38 - Watch Going Solo: Navigating Your Financial Future Single YMYW TV, Download the Going Solo Guide 29:25 - I'm 43 With $50K and a Paid Off House. Can I Retire ASAP? (Old MacDonald, Limington, Maine) 37:35 - I'm 35 With $1.4M. Can I Retire at 45 and Spend $75K/year? (Conshohocken Curt, PA) 49:04 - Next Week on the YMYW Podcast 49:23 - YMYW Podcast Outro

Your Roth Conversion Strategy Needs This Update - 545 Sep 02, 2025

One Big Beautiful Bill is now law. How does it impact your Roth conversion strategies and other financial decisions? Plus, you may have seen or heard other advisors talking about their strategies for getting your retirement savings into tax-free Roth accounts. How are these different from a good ol' Roth conversion, and what do Joe and Big Al think of them? Find out today on Your Money, Your Wealth® podcast number 545 with Joe Anderson, CFP® and Big Al Clopine, CPA. Also, why is Ed Slott, CPA, the man known to many as "the IRA guru," such a fan of permanent cash value life insurance? Finally, an attempted correction from a YMYW YouTube viewer turns into a rousing game of death trivia, and we'll share some of your opinions from the 8th Annual YMYW Podcast Survey, which just closed. (Congratulations Larry, for being the randomly-chosen winner of the $100 Amazon e-gift card, just for completing the survey!)

Free financial resources & episode transcript: https://bit.ly/ymyw-545

DOWNLOAD The Ultimate Guide to Roth IRAs

WATCH Your 11 Step Path to Financial Freedom on YMYW TV

CALCULATE your free Financial Blueprint

SCHEDULE your Free Financial Assessment

ASK Joe & Big Al for your Retirement Spitball Analysis

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

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JOIN THE CONVERSATION on YouTube

DOWNLOAD more free guides

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Your Retirement Tax Strategy is Probably Unbalanced - 544 Aug 26, 2025

You've heard Joe and Big Al talk about the benefits of tax diversification in retirement. That is, having money in tax-deferred, tax-free, and taxable accounts. But what should you do if this tax triangle of yours is lopsided? Joe and our special guest co-host, Marc Horner, CFP®, spitball on this quandary for Rae and Roy in Central California, today on Your Money, Your Wealth® podcast number 544. Plus, do Rae or Roy need to get a part-time job? Also, "Elwood Blues" in Illinois would like to retire in two years, but is willing to go for 3 more to make his retirement plan work. Joe and Marc spitball on when "Elwood" can really put down that harmonica.

Free financial resources & episode transcript: https://bit.ly/ymyw-544

Complete the 8th Annual YMYW Podcast Survey by 5pm Pacific on August 31, 2025, for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

WATCH 15 Maneuvers to Duck an Unplanned Early Retirement Knockout on YMYW TV

CALCULATE your free Financial Blueprint

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

SUBSCRIBE or FOLLOW on your favorite podcast app

JOIN THE CONVERSATION on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast with Joe Anderson, CFP® and Marc Horner, CFP®

00:49 - Our Tax Triangle is Lopsided. Should One of Us Get a Part-Time Job? (Rae and Roy, Central CA)

12:03 - Watch 15 Maneuvers to Duck an Unplanned Early Retirement Knockout, Calculate your Financial Blueprint, Schedule a Financial Assessment

13:11 - I'd Like to Retire in 2 Years. Willing to Work 3 More to Make it Work (Elwood Blues, IL)

27:10 - Next Week on YMYW Podcast: The One Big Beautiful Bill + More

27:40 - YMYW Podcast Outro

Can You Retire at Age 57 and Spend Big? - 543 Aug 19, 2025

Is it possible, common even, to spend a lot early in retirement to celebrate your financial freedom? How do Roth conversions and withdrawals work if you do plan to call it quits around age 57, and spend big early on? Should you convert retirement funds to tax-free Roth after you stop working? Joe Anderson CFP® and our special guest co-host, Marc Horner, CFP® spitball on these topics for "Beavis and Daria" in Texas and "Clark Kent" in Pennsylvania, today on Your Money, Your Wealth® podcast number 543. Plus, the sooner 56-year-old "Tony Soprano" in New Jersey can retire, the better. What tips do Joe and Marc have for him? By the way, Marc is one of the newest principals here at Pure Financial Advisors. He's the founder of Fairhaven Wealth Management, which has just become the newest Pure Financial Advisors Chicagoland office in Wheaton, Illinois - so help us welcome him for his YMYW debut.

Free financial resources & episode transcript: https://bit.ly/ymyw-543

Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

DOWNLOAD the Withdrawal Strategy Guide for free

WATCH Withdrawal Trap Doors on YMYW TV

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts

SUBSCRIBE or FOLLOW on your favorite podcast app

JOIN THE CONVERSATION on YouTube

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:00 - Spending Higher Earlier in Retirement to Celebrate? How to Convert? Where to Withdraw? (Beavis & Daria, TX)

12:30 - Watch Withdrawal Trap Doors on YMYW TV and Download the Withdrawal Strategy Guide for free

13:36 - Can I Retire at 57 Even With a High Draw Down Rate? Should I Convert After Retirement? Should I Consider an Annuity? (Clark Kent, PA)

28:23 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

29:09 - When Can I Retire? The Sooner the Better. (Tony Soprano, NJ)

37:43 - Next Week on the YMYW Podcast

38:01 - YMYW Podcast Outro

Are You Cutting Retirement Too Close? - 542 Aug 12, 2025

"Rubble and Skye" in Minnesota want to spend $65,000 a year in retirement, and they'll have $67K in annual fixed income. Are they cutting it too close? "Atouk and Tala" in New Jersey will have retirement money, Social Security, and "Lumpy," their lump sum pension - will they be okay? We'll find out today on Your Money, Your Wealth® podcast number 542 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, should David in Redondo Beach California use his Roth money to buy a home? And what do the fellas think about "Charlie Pepper" in Colorado using a home equity line of credit (HELOC) for retirement spending, instead of living off of pre-tax money?

Free financial resources & episode transcript: https://bit.ly/ymyw-542

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:43 - $250K Saved, $67K Fixed Income, $65K Spending. Are We Cutting Retirement Too Close? (Rubble & Sky, MN)

05:20 - We Have a $700K Pension, $335K Retirement, Plus Social Security. Will We Be OK? (Atouk and Tala, NJ)

13:14 - Watch Financial Boot Camp on YMYW TV, Download the Investing Basics Guide

14:03 - Should I Use My Roth Money for a Home Purchase? (David, Redondo Beach, CA)

21:03 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

22:01 - HELOC vs. Pre-Tax Account for Retirement Spending (Charlie Pepper, CO)

34:23 - Next Week on YMYW Podcast: Guest Co-Host Marc Horner, CFP®

34:53 - YMYW Podcast Outro

Are These Millennials Saving Enough to Retire Before 60? - 541 Aug 05, 2025

Pam and Jim in Phoenix are 38 and 41 and want to retire at 59 and 62. Matt and his wife in Pennsylvania are both 39 and want to retire at 57. Are these millennials on the right financial path, or have they brunched and YOLO'd away their retirement dreams? That's today on Your Money, Your Wealth® podcast number 541 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, do Roth conversions make sense for Will and Jane in New York, given their high income and high tax bracket? Which pension option is best for their circumstances? Finally, the fellas spitball for Juan's mother in Florida on how long-term capital gains on the installment sale of her company will be taxed.

Free financial resources & episode transcript: https://bit.ly/ymyw-541

Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw)

LIMITED TIME OFFER: Download The Money Makeover Guide before this Friday, August 8, 2025!

WATCH Complete Money Makeover on YMYW TV

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:44 - We're Millennials. Have We Brunched and YOLO'd Away Our Retirement Dreams? (Pam & Jim, Phoenix, AZ)

12:10 - We're 39 With $840K. Can We Retire at Age 57? (Matt, PA)

22:57 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card!

23:53 - Do Roth Conversions Make Sense Given Our High Income and Tax Bracket? What Pension Option is Best? (Will and Jane, NY - voice)

37:04 - Watch Complete Money Makeover on YMYW TV, Download the Complete Money Makeover Guide before Friday, August 8, 2025!

37:46 - How Will Long Term Capital Gains on the Installment Sale of My Company Be Taxed? (Juan's Mother, FL)

47:50 - YMYW Podcast Outro

Retire Early and Spend More Without Running Out of Money - 540 Jul 29, 2025

Can Beth and Rip retire early, spend more, and Die with Zero? When should they claim Social Security? Forrest and Jenny have 10 rental properties at age 31. Can they retire at age 50? (And what makes you a real estate professional from a tax perspective?) Plus, what are the rules for spousal IRA contributions and required minimum distributions? Memphis wants to know. Joe Anderson, CFP® and Big Al Clopine, CPA spitball for YMYW audience members who are definitely not fictional characters, today on Your Money, Your Wealth® podcast number 540.

Free financial resources & episode transcript: https://bit.ly/ymyw-540

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Timestamps:

00:00 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card!

00:35 - Intro: This Week on the YMYW Podcast

01:13 - Can We Retire Early, Spend More, and Die With Zero? When Should We Collect Social Security? (Beth and Rip, FL - voice)

12:06 - Watch Retirement Panic Button: 7 Ways to Avoid Hitting It on YMYW TV

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13:41 - We Have 10 Rental Properties at Age 31. Are We on Track to Retire at Age 50? (Forrest and Jenny, Cherry Hill, NJ - voice)

20:04 - Spousal IRA Contributions and RMD Rules (Memphis)

32:23 - YMYW Podcast Outro

Where to Invest for Pre-Retirement and a GO-GO Lifestyle? - 539 Jul 22, 2025

Roger in Canton, Ohio, is burnt out. Can he and his wife Jane pre-retire next year in their mid-50s with $2.8 million? Joe and Big Al spitball on whether they'll still have enough money for their Go-Go years, Joe's favorite, today on Your Money, Your Wealth® podcast number 539. Roger also has an employee stock purchase plan. For the best asset location strategy, should he max out the ESPP at a 15% discount, convert to Roth IRA, build his brokerage account, or a little of all the above? Speaking of asset location, some of our YouTube viewers object to the idea of putting higher performing assets in your Roth account. They say you can't write off the losses and you'll be exposed to sequence of returns risk. Stick around for Joe and Al's response.

Free financial resources & episode transcript: https://bit.ly/ymyw-539

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

02:03 - I'm Burned Out. Can I Pre-Retire Next Year? (Roger & Jane, Canton, OH)

11:46 - Watch Recipe for Retirement | Retirement Plans Explained on YMYW TV and Calculate Your Free Financial Blueprint

12:50 - Would You Rather for Asset Location: Roth vs. Brokerage? Roth vs. ESPP with 15% Discount? (Roger & Jane, Canton, OH, cont'd)

21:08 - Higher Performing Assets in Roth Exposes You To Sequence of Returns Risk and You Can't Write Off The Losses (YouTube comment)

24:54 - Next Week on the YMYYW Podcast

25:27 - Download Why Asset Location Matters for Free

How Much Money Do You Need to Retire in 2026? - 538 Jul 15, 2025

George and Weezy in the land of Lincoln will have deferred compensation and wonder if they can retire in mid-2026, or even earlier. Will they have enough? Should Jenn in Ohio move with work, take a break, or just retire? She asks Joe Anderson, CFP® and Big Al Clopine, CPA for a brutally honest spitball, today on Your Money, Your Wealth® podcast 538. Plus, Seth isn't sure if he can afford to stay retired at age 52, and whether he should convert his retirement savings to Roth, so he uses an AI voice to ask the fellas for his spitball. And Leon uses his real voice to ask whether REIT ETFs are a good way to get into real estate investing.

Free financial resources & episode transcript: https://bit.ly/ymyw-538

Test your knowledge: take our Retirement Pop Quiz

Watch Retirement Pop Quiz: 18 Questions To Get You Ready to Retire on YMYW TV

Download the Retirement Readiness Guide for free

Email Us and Request a Free Copy of The Best of Jonathan Clements: Classic Columns on Money and Life on Kindle!

Watch or Listen to "The Payoff is Huge": Jonathan Clements' Final Initiative to Empower Lifelong Savers

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:03 - Can "George and Weezy" Retire in 2026 or Earlier With Deferred Compensation? (IL)

12:17 - Pop Quiz, Retirement Readines Guide

13:02 - Should I Move With Work, Take a Break, or Retire Now? Be Brutally Honest (Jenn, OH)

17:43 - Can I Stay Retired at Age 52? Should I Convert Retirement Savings to Tax-Free Roth? (Seth, Montana, AI voice)

24:34 - Ask Joe & Big Al for your Retirement Spitball Analysis, Schedule a Free Financial Assessment

25:30 - Are REIT ETFs a Good Way to Get Into Real Estate Investing? (Leon, Chicago - voice)

33:56 - Request a Free Kindle Copy of The Best of Jonathan Clements, Watch or Listen to "The Payoff is Huge": Jonathan Clements' Final Initiative to Empower Lifelong Savers

Late Start on Roth Savings? Here's What to Prioritize - 537 Jul 08, 2025

You've got your tax-free Roth accounts and your tax-deferred retirement accounts. Should you invest the same way in each? Kevin in Denver wants to know. Jim and Pam in Orange County are eligible for combat zone tax exclusions (CZTE). How else can they maximize their tax-free retirement strategy? Susan Brandeis, CFP® spitballs with Big Al Clopine, CPA, today on Your Money, Your Wealth® podcast number 537. Plus, should Ned in Tokyo sell his Bay Area rental property and invest the proceeds? And Bob and Brigette in Wisconsin got a late start on Roth IRA savings. Should they prioritize saving into a Roth, brokerage account, or 401(k)?

Free financial resources & episode transcript: https://bit.ly/ymyw-537

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:46 - Should the Asset Location of Our Accounts Be Independent of Each Other? (Kevin, Denver)

08:54 - CTZE - Any Other Ways to Maximize Our Tax-Free Retirement Strategy? (Jim & Pam, Orange County)

17:19 - Watch How to Build a Recession-Proof Portfolio on YMYW TV, Download the Recession Protection Guide

18:00 - Should We Sell a Rental Property and Invest the Proceeds? (Ned, Tokyo, Japan)

25:37 - Got a Late Start on Roth IRA Savings. Should I Prioritize Roth, Brokerage, or 401(k)? (Bob & Bridgette, WI)

34:49 - Next Week on YMYW Podcast

Social Security Rules Changed: Your Pension Doesn't Matter Anymore - 536 Jul 01, 2025

If your pension impacted your ability to collect Social Security benefits, 2025 is a very good year for you and your spouse. The Windfall Elimination Provision and the Government Pension Offset are no more, and you're now eligible for your full Social Security benefits AND your pension! Today on a quick Your Money, Your Wealth® podcast number 536, while Joe hangs in the North Star State, Big Al Clopine explains what the Social Security Fairness Act means for Cherilyn and her husband, and "Nuke La Loosh" and his wife, with the help of our special guest co-host, Susan Brandeis, CFP®.

Free financial resources & episode transcript: https://bit.ly/ymyw-536

DOWNLOAD The Social Security Handbook (newly updated!) for free

YMYW ranked among the "14 Best Retirement Podcasts and Blogs to Follow" by Due.com, featured on NASDAQ.com

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:47 - Can I Qualify for Half of My Wife's Social Security Now That WEP and GPO Are Gone? (Nuke La Loosh, Northern CA - voice)

08:16 - Is My Husband Eligible for Spousal Social Security Benefits Now that WEP and GPO Are Gone? (Cherilyn, El Cajon, CA)

12:58 - Comment: Your TV Show and Guide on Social Security Are Out of Date (Helen, San Diego)

14:11 - Comment: Even If the TV Show Doesn't Pertain to You Directly, You Can Inform Someone Else (Catherine)

14:39 - Social Security Handbook (newly updated!) - download for free

15:00 - YMYW ranked among the "14 Best Retirement Podcasts and Blogs to Follow" by Due.com, featured on NASDAQ.com

15:21 - Next Week on the YMYW Podcast

When Do Roth Conversions STOP Making Sense? - 535 Jun 24, 2025

Ryan in Texas is in the 32% tax bracket. Where should he save for retirement so he'll be in a lower bracket? Should Weronika in Texas pay the taxes now to convert to Roth for lifetime tax-free growth in the future, even though she's in the 37% tax bracket? And Jerry in Phoenix wonders if there is a point where Joe would come to the conclusion that Roth conversions no longer make sense? Stay tuned for the 7 reasons to consider NOT converting to Roth, today on Your Money, Your Wealth podcast number 535 with Joe Anderson, CFP® and Big Al Clopine, CPA. First up, a word of Roth conversion thanks from Al in Florida.

Free financial resources & episode transcript: https://bit.ly/ymyw-535

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RETIREMENT CALCULATION TOOLS:

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Insult to a Nose (Scene from Steve Martin movie "Roxanne" - warning, language!)

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:44 - Thanks for Suggesting a Roth Conversion During the Market Drop (comment from Al, FL)

03:38 - In the 32% Tax Bracket. Where Should I Save for Retirement to Be in a Lower Bracket? (Ryan, TX)

07:57 - In the 37% Bracket: Backdoor Roth or Non-Roth Investments for Retirement Savings? (Weronika, TX)

12:25 - Watch The Last 5 Years Before Retirement Will Decide Your Lifestyle - Here's How on YMYW TV. Calculate your free Financial Blueprint

13:23 - Is There a Point Where Roth Conversions No Longer Make Sense? (Jerry, Phoenix, AZ)

25:26 - YMYW Podcast Outro

Roth Conversions vs. IRMAA, Using Retirement Funds to Pay the Mortgage, Retirement Spending Plan - 534 Jun 17, 2025

Ralph and Alice in Monument, Colorado have $4.6 million dollars saved at ages 63 and 58. Should they do Roth conversions? How do they avoid IRMAA? Mary Jo in Escondido, California wonders if she should use her 403(b) money to pay off her mortgage. And Lucas plans to spend from his brokerage, then his 401(k), then his Social Security and pension when he retires in 20 years. What do Joe and Big Al think of his strategy? Find out today on Your Money, Your Wealth® podcast 534.

Free financial resources & episode transcript: https://bit.ly/ymyw-534

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DOWNLOAD The Retirement Readiness Guide

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:55 - We're 63 and 58 With $4.6M Saved. Should We Do Roth Conversions? Can We Avoid IRMAA? (Ralph & Alice, Monument, CO - voice)

11:51 - Watch Is There a Formula for Retirement? on YMYW TV, Download The Retirement Readiness Guide for free

12:59 - Should I Use My 403(b) Pay Off My Mortgage? (Mary Jo, Escondido)

16:48 - Brokerage to 401(k) to Social Security and Pension: Good Income Strategy for Retirement in 20 Years? (Lucas)

26:33 - YMYW Podcast Outro

Early Withdrawals, Tech Stocks vs. International, Annuities, ESOP and NUA - 533 Jun 10, 2025

Before she retires next month at age 52, Rowan in Georgia wonders how to maximize growth in her IRA, which will be funded with 72(t) early retirement withdrawals. What do Joe Anderson, CFP® and Big Al Clopine, CPA think of her substantially equal periodic payment plan? And how should she allocate it? Michael in Virginia isn't interested in any international investments and is instead invested in stocks like Google, Amazon, Microsoft, Meta, and Berkshire. What adjustments would the fellas make to his portfolio for long term growth? That's today on Your Money, Your Wealth® podcast 533. Plus, our friend Will, who is not a gas siphoner, wants Joe and Big Al's opinion on "backdoor Rothing" his solo 401(k) instead of having an emergency fund, and on what he should do with his annuity. Also, the fellas explain ESOP and NUA - that is, employee stock ownership plans and net unrealized appreciation - for Tess and Finn in Texas.

Free financial resources & episode transcript: https://bit.ly/ymyw-533

WATCH 10 Big Retirement Regrets to Avoid (Before It's Too Late) on YMYW TV

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The origins of Will the Gas Siphoner (audio only)

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:05 - How Do I Maximize My 72(t) Early Retirement Withdrawals? (Rowan, GA - voice)

10:24 - Watch 10 Big Retirement Regrets to Avoid (Before It's Too Late) on YMYW TV, Calculate your free Financial Blueprint

11:23 - I'm Not Interested in International Investments. Does My Asset Allocation of Tech Stocks Make Long-Term Sense? (Michael, VA)

14:18 - Should I Backdoor Roth My Solo 401(k) Income Instead of Having an Emergency Fund? What Should I Do With My Annuity? (Will the Gas Siphoner)

24:44 - Schedule a Free Financial Assessment With Pure Financial Advisors

25:53 - ESOP and NUA Explained (Tess & Finn, TX)

31:53 - Tribute to Betsey Clopine, 1933 - 2025

33:17 - YMYW Podcast Outro

"The Payoff is Huge": Jonathan Clements' Final Initiative to Empower Lifelong Savers - 532 Jun 03, 2025

Imagine being told you only have 12 months to live. What would you do with your time? Today on Your Money, Your Wealth podcast number 532, Big Al Clopine, CPA and Executive Producer Andi Last are thrilled to welcome Jonathan Clements back for his fourth appearance. For thirty years, Jonathan has been known for his personal finance writing: in his column "Getting Going," which appeared in the Wall Street Journal over 1,000 times starting in 1994, on his website HumbleDollar.com, and in his many acclaimed books. About a year ago, Jonathan Clements was diagnosed with a rare form of lung cancer and was told he had about a year to live. Today we're celebrating the fact that he is still here with us, and we're inspired by his decision to use his precious time to launch The Jonathan Clements Getting Going on Savings Initiative. Watch or listen to find out how you can get a free Kindle copy of Jonathan's new book, and how you can help Jonathan pay it forward for the next generation.

Free financial resources & episode transcript: https://bit.ly/ymyw-532

The first 100 people to email us will receive a free Kindle copy of The Best of Jonathan Clements: Classic Columns on Money and Life

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

02:53 - Jonathan Clements' Getting Going on Savings Initiative

05:23 - $1,000 Roth IRA Contributions and Personal Finance Education for Young Adults

07:55 - Exponential Growth: The Sooner You Save, The Better

09:44 - Research Study Will Measure Impact on Young Savers

11:56 - Financial Education is Important

14:05 - The John C. Bogle Center for Financial Literacy

14:38 - The First 100 People to Email Us Receive a Free Copy of The Best of Jonathan Clements: Classic Columns on Money and Life

15:45 - How Does a Healthy 62-Year-Old Non-Smoker End Up Living With Stage IV Lung Cancer? The EGFR Exon 20 Insertion Mutation

18:52 - HumbleDollar.com, The Jonathan Clements Getting Going on Savings Initiative, and The Best of Jonathan Clements Book

Tariffs Killed My Portfolio. Should I Claim Social Security Early? - 531 May 27, 2025

Tariffs killed Carl's investment portfolio and left him wondering if he should claim Social Security early. Joe Anderson, CFP® and Big Al Clopine, CPA spitball for him today on Your Money, Your Wealth® podcast number 531. Kelly and Steve in Pennsylvania ask for a three-fer spitball - when to claim their Social Security, whether they should contribute to Roth or convert to Roth for that lifetime tax-free growth on their investments, and if they're on track for Kelly to retire in three years.

Free financial resources & episode transcript: https://bit.ly/ymyw-531

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:21 - Tariffs Killed My Portfolio. Should I Claim Social Security Early? (Carl)

10:14 - Watch The Retirement Course: Can You Hit a Hole in One? on YMYW TV, Calculate your free Financial Blueprint

11:13 - When Should We Claim Social Security? Roth Contributions or Conversions? Are We On Track for Retirement? (Kelly & Steve)

25:00 - Download the Key Financial Data Guide, YMYW Podcast Outro

Portfolio Drift, Avoiding Capital Gains, and a $6M Retirement - 530 May 20, 2025

What should you do when the asset allocation of your retirement portfolio drifts? Joe Anderson, CFP® and Big Al Clopine, CPA spitball on rebalancing for DJ in St. Louis, today on Your Money, Your Wealth® podcast number 530. Plus, Coach Dobber in Minnesota is curious about municipal bonds in a brokerage account, and Daniel in Stevensville, Michigan needs details on emergency funds. Also, can Tim the Enchanter do a Roth conversion and avoid the nasty big pointy teeth of capital gains tax? And, Duke in upstate New York told his wife they need 6 million dollars in retirement, and she said he was silly. What say Joe and Al? We'll find out.

Free financial resources & episode transcript: https://bit.ly/ymyw-530

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast 00:47 - Rebalancing Asset Allocation of US Stocks, International Stocks, and Bonds (DJ in St Louis) 07:21 - Can I Do a Roth Conversion and Have No Cap Gains Tax? (Tim the Enchanter, FL) 15:44 - Watch Financial Planning at Every Age on YMYW TV, Download the Retirement Readiness Guide for free 16:41 - Municipal Bonds in a Brokerage Account: Good Idea? (Coach Dobber, MN) 22:48 - Told My Wife We Need $6M to Retire in 20 Years. She Say's I'm Silly. (Duke, upstate NY) 27:09 - Calculate your Free Financial Blueprint, Schedule your Free Financial Assessment 28:54 - What Is an Emergency Fund and How Much Should I Have in It? (Daniel, Stevensville, MI) 36:00 - YMYW Podcast Outro

When to HOLD OFF on Doing Roth Conversions - 529 May 13, 2025

John in Boston is in the 32% tax bracket. Should he do Roth conversions? Flight Deck Dad and Irish Girl in Pensacola have a lot of tax-free pension income. Should they do Roth conversions? Bert and Ernie in New Jersey wonder if they should convert to Roth or take advantage of zero percent capital gains tax rates. Joe Anderson, CFP® and Big Al Clopine, CPA spitball for all of them today on Your Money, Your Wealth® podcast number 529. Plus, Michael and his wife in Bellevue are 34, in the 24% tax bracket and wonder if they should contribute to tax-free or tax-deferred accounts, and if they should slow down on retirement savings and start a bridging account for the years between when they want to punch the clock in their early to mid-50s, and when they can access their retirement savings. Then, for something completely different, Frenchie from Maine writes back in: What are the disadvantages to paying off her mortgage ASAP, and what's the tax efficiency of a money market compared to bond funds?

Free financial resources & episode transcript: https://bit.ly/ymyw-529

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:00 - We're in the 32% Tax Bracket. Should We Do Roth Conversions? (John, Boston, MA)

06:19 - We Have Large Tax-Free Pension Income. Should We Do Roth Conversions? (Flight Deck Dad & Irish Girl, Pensacola, FL)

16:03 - Watch How to Break Through Retirement Barriers on YMYW TV, Calculate your free Financial Blueprint

16:52 - Should We Do Roth Conversions or Take Advantage of 0% Capital Gains Tax? (Bert & Ernie, NJ)

25:53 - In the 24% Bracket. Should We Contribute to Tax-Free or Tax Deferred Accounts? (Michael, Bellevue, WA)

29:49 - Schedule a Free Financial Assessment at any of Pure Financial Advisors' 12 nationwide locations or online

31:04 - Disadvantages to Paying Off the Mortgage ASAP? Tax Efficiency of Money Market vs. Bond Funds? (Frenchie, ME)

36:23 - Outro: Next Week on the YMYW Podcast

Retirement Savings: When to Take Your Foot Off the Gas - 528 May 06, 2025

You've been jamming money into your retirement accounts for years now. When is it okay to slow down? Joe Anderson, CFP®® and Big Al Clopine, CPA spitball for Ron and Veronica in Indiana today on Your Money, Your Wealth® podcast 528. Plus, how can Scott in Illinois bridge the gap from age 55 to retirement income at 57? How should Big Juan in Texas pay for college? Should he convert his TSP to Roth? Can he retire at 55 And finally, Frank and Jane Drebin in Wisconsin are 46 and 47 and wondering if their plan for retirement in 5 years is just a pipe dream.

Free financial resources & episode transcript: https://bit.ly/ymyw-528

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:13 - Can I Take My Foot Off the Gas on Saving for Retirement? (Ron and Veronica, IN)

09:48 - Watch What Happens to Your 401(k) & IRA at Retirement? On YMYW TV and Download The Retirement Readiness Guide

10:43 - How to Bridge the Gap from Age 55 to Retirement Income at 57? (Scott, IL)

20:04 - How to Fund College? TSP to Roth Conversions? Retirement at 55? (Big Juan, TX)

24:45 - Calculate Your Free Financial Blueprint

25:45 - We're 46 and 47, Is Our Retirement Plan a Pipe Dream? (Frank and Jane Drebin, WI)

32:26 - Next Week on the YMYW Podcast

Taxable Income, Dividends, Roth & SMA: What's Missing in Your Early Retirement? - 527 Apr 29, 2025

What are the pros and cons if Chip uses the money in his taxable brokerage account for early retirement income? Jack and Sally ask Joe and Big Al to spitball on whether they can retire around age 55 or 60, and whether they should max out their Roth or convert to Roth, today on Your Money, Your Wealth® podcast 527 with Joe Anderson, CFP®, and Big Al Clopine, CPA. Plus, April and Andy ask the fellas to spitball on their dividend investing strategy, and Don wonders if a separately managed account (SMA) makes sense for his taxable account. (We'll also find out what an SMA is.)

Free financial resources & episode transcript: https://bit.ly/ymyw-527

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:52 - Pros and Cons of Using a Taxable Brokerage Account for Early Retirement Income? (Chip Skylark, Dimsdale)

13:24 - Watch Your 11-Step Path to Financial Freedom on YMYW TV, Calculate Your Free Financial Blueprint

14:27 - Is My Dividend Investing Strategy Missing Anything? (Andy & April, Knoxville, TN)

25:02 - Can I Retire Between Ages 55-60? Should I Max Out Roth Contributions, or Convert to Roth? (Jack & Sally, NC)

31:18 - Download the Withdrawal Strategy Guide and 10 Steps to Improve Investing Success for Free

32:03 - Does a Separately Managed Account (SMA) Make Sense for My Taxable Account? (Don, IA)

40:46 - Next Week on the YMYW Podcast

Roth IRA is "The Greatest Account Ever" Per Ed Slott. But Why? - 526 Apr 22, 2025

Just about every week here on YMYW, Joe and Big Al talk about converting your retirement savings to Roth accounts. But why? What's the big deal? Today the "IRA guru" Ed Slott, CPA returns to Your Money, Your Wealth® in podcast number 526 with Joe Anderson, CFP® and Big Al Clopine, CPA to tell us why he calls the Roth IRA "the greatest account ever created." (Here's a hint: it's all about having tax-free income in retirement - and beyond.) Plus, where to prioritize saving for retirement? Jerry Tom in St. Louis wants to know. Are Christian and Tiffany in Montana on track for retirement, and should they rebalance their ETFs? Should Frank in Lake Wobegon's wife take her teachers' salary over 9 months or 12 months? And finally, Jon thinks the target retirement withdrawal rates Joe and Big Al use to spitball are too low - we'll see what they think.

Free financial resources & episode transcript: https://bit.ly/ymyw-526

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Timestamps:

00:00 - Intro

00:59 - Ed Slott, CPA on the Roth IRA, the Future of Taxes, the Death of the Stretch IRA, and Naming a Trust as Your Retirement Account Beneficiary

19:44 - Download The Complete Roth Papers Package for free

20:37 - Where to Prioritize Saving for Retirement? (Jerry Tom, St. Louis)

28:57 - Are We on Track for Retirement? Should We Rebalance Our ETFs? (Christian & Tiffany, Montana)

40:43 - Watch Don't Let These 10 Risks Break Your Retirement on YMYW TV, Calculate Your Free Financial Blueprint

41:44 - Is It Better to Take Teachers' Salary Over 9 Months or 12? (Frank, Lake Wobegon - voice)

45:32 - Withdrawal Rates Are Very Low on YMYW (Jon, Twitter & Apple Podcasts)

49:46 - YMYW Podcast Outro

Risks Threaten Retirement. Rewire Your Plans - 525 Apr 15, 2025

Tariffs, inflation, healthcare costs... how do you shift from saving to spending in retirement while managing risks like these? Jamie Hopkins is a CERTIFIED FINANCIAL PLANNER® professional, an attorney, and best-selling author of Find Your Freedom and Rewirement: Rewiring the Way You Think About Retirement. He returns to the show today on Your Money, Your Wealth® podcast 525 with Joe Anderson, CFP® and Big Al Clopine, CPA, to share insights on how to rewire your retirement plans. Plus, how should Fred and Ginger in Huntington Beach, California, pay for repairs on their rental properties? How can Peter Lemonjello manage taxes in his early retirement with 72(t) elections, rental income, and an installment sale? Can Calvin and Susie in Lancaster, Pennsylvania, buy an $800,000 beach house - and should they?

Free financial resources & episode transcript: https://bit.ly/ymyw-525

DOWNLOAD The Recession Protection Guide

WATCH the Market Volatility webinar with Joe Anderson, CFP® and Brian Perry, CFP®, CFA from Pure Financial Advisors on demand

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Thanks to Million Podcasts for ranking YMYW in several of their "Best of" lists! Read more.

Timestamps:

00:00 - Intro

00:59 - Rewiring Spending and Managing Risk in Retirement with Jamie Hopkins Esq., LLM, CFP®, ChFC®, CLU®, RICP®

24:07 - Watch the Market Volatility Webinar On Demand, Download the Recession Protection Guide

24:52 - How Should We Pay for Repairs on Rental Properties? (Fred & Ginger, Huntington Beach, CA)

33:06 - Early Retirement Taxes: 72(t) Timing, Installment Sale, and Rental Income (Peter LemonJello, FL)

44:02 - Watch How Your Home Can Create Retirement Income on YMYW TV, Download 10 Tips for Real Estate Investors

44:33 - Can and Should We Buy an $800K Beach House? (Calvin and Susie, Lancaster, PA)

53:33 - YMYW Podcast Outro

Will the Tax Cuts and Jobs Act Be Extended? - 524 Apr 08, 2025

Will your taxes go up? Stay the same? Go down, even? Jeffrey Levine is Chief Planning Officer at Focus Partners, Professor of Practice in Taxation at the American College of Financial Services, and the Lead Financial Planning Nerd at Kitces.com. In other words, he's one of the savviest tax minds in the country. Jeff returns to the show today on Your Money, Your Wealth® podcast number 524 with Joe Anderson, CFP® and Big Al Clopine, CPA, with his thoughts on what will happen to taxes under the new administration, saving for retirement in a Roth IRA vs. a traditional IRA, managing inherited retirement accounts, and the future viability of Social Security. Plus, what should you do with required minimum distributions when you don't need the money to live on? How do you calculate the maximum amount you should convert from your retirement account to a tax-free Roth account, and how much should you convert - or not - to keep RMDs under control? Finally, how can minor beneficiaries avoid probate?

Free financial resources & episode transcript: https://bit.ly/ymyw-524

LIMITED TIME SPECIAL OFFER: DOWNLOAD The DIY Retirement Guide by Friday April 11, 2025!

WATCH Take Control of Your Retirement Plan on YMYW TV

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:05 - Will These Historic Low Tax Rates Be Extended? Insight from Jeff Levine, CFP®, CPA/PFS, ChFC®, RICP®, CWS, AIF, BFA™, MSA

19:54 - Make These 3 Investments for a Happy Retirement and Watch Take Control of Your Retirement Plan on YMYW TV

21:06 - What to Do With Required Minimum Distributions When You Don't Need the Money to Live On? (Judi, San Diego)

24:40 - How Much NOT to Convert to Roth to Keep RMDs Under Control? (DH from SoCal)

32:26 - LIMITED TIME SPECIAL OFFER: Download the DIY Retirement Guide by Friday, April 11, 2025!

33:39 - How to Calculate How Much Roth Conversion I Should Do? (Joe, voice)

38:42 - How Can I Reduce My Required Minimum Distributions? (Joel, CA)

40:18 - How Can Minor Beneficiaries Avoid Probate? (Esther, San Francisco)

46:04 - YMYW Podcast Outro

These Three Investments Make for a Happier Retirement - 523 Apr 01, 2025

What are the three predictors of retirement happiness? Dr. Michael Finke, CFP® from the American College of Financial Services tells us what his research shows. He also shares his insights on the four percent rule for retirement withdrawals and whether there is anything we can do to stave off the effects of aging on our cognitive abilities. That's today on Your Money, Your Wealth podcast number 523 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Joe and Big Al do some retirement spitballing: can Jon in Pennsylvania retire early at age 56, and would it be better for him to take his pension monthly or as a lump sum? Steve and his wife in Colorado are 48 and 54 and have $3 million saved. When can they retire? Eager Eagle and his wife in Washington state have $2 million saved at ages 61 and 63. Can they retire next year?

Free financial resources & episode transcript: https://bit.ly/ymyw-523

DOWNLOAD The Retirement Lifestyles Guide

DOWNLOAD The Social Security Handbook

WATCH: Social Security Basics You Need to Know: Common Social Security Questions Answered on YMYW TV

WATCH/LISTEN: What's Your Retirement Income Style?

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Choosing Your Retirement Income Style and Top 5 Ways to Manage Market Volatility - 522 Mar 25, 2025

What is your retirement income style? Dr. Wade Pfau, CFA, RICP®, is the co-founder of RISAprofile.com, providing investors with retirement income style awareness. He returns to Your Money, Your Wealth® today on podcast number 522 to talk about four different styles of retirement income, distribution planning and the four percent rule. Plus, what does Dr. Pfau think will happen with President Trump's 2017 tax cuts, scheduled to sunset at the end of this year? What are Dr. Pfau's thoughts on annuities as part of your retirement plan? Next, "Joe Anderson's Top 5 Things" to help you manage the impact of all this market volatility on your portfolio. Also, Joe Anderson CFP® and Big Al Clopine, CPA spitball for "Al Bundy" in St. Louis: what withdrawal strategy makes sense for him, and what he should do with his IRA and 401(k) money?

Free financial resources & episode transcript: https://bit.ly/ymyw-522

DOWNLOAD the Recession Protection Guide

DOWNLOAD The Tax Planning Guide

WATCH Escape These 11 Tax Traps and You'll Save in Retirement on YMYW TV

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:00 - Retirement Income Style, Tax Laws, and Annuities with Dr. Wade Pfau

16:39 - What's the Future of Your Social Security? Watch Last Week's YMYW Podcast & Subscribe on YouTube

17:08 - Joe Anderson's Top 5 Things: How to Manage Market Volatility

26:27 - Learn to Escape These 11 Tax Traps and You'll Save in Retirement on YMYW TV, Download the Tax Planning Guide

27:13 - What Should I Do With My IRA and 401(k)? I'm 61 and Have $10M. (Al Bundy, St. Louis)

00:00 - YMYW Podcast Outro

What's the Future of Social Security Under the New Administration? - 521 Mar 18, 2025

What does the future hold for your Social Security under the new Trump administration and Elon Musk's DOGE, the Department of Government Efficiency? Nationally-renowned financial thought leaders Jamie Hopkins, Jeff Levine, Eric Ludwig, and Steve Parrish share their insights with Big Al Clopine, CPA at the American College of Financial Services' Horizons Conference in San Diego, CA on Your Money, Your Wealth® podcast 521. First, the College's President, George Nichols, gives a brief overview of the institution and their inaugural conference.

Plus, Joe Anderson, CFP® and Big Al spitball on whether Ricky and Lucy in Wisconsin even bother saving for retirement - they're expecting to inherit about 20 million dollars. When should Tybob in Arizona collect Social Security? Are Roth conversions right for him? Should he go for Medicare or Medicare Advantage? Speedy Racer in Georgia needs a retirement spitball, and Gilligan in New York shares insight for other Gilligans trying to avoid a retirement shipwreck.

Free financial resources & episode transcript: https://bit.ly/ymyw-521

DOWNLOAD the Social Security Handbook

WATCH Are You Ready for Retirement? On YMYW TV

DOWNLOAD the Retirement Readiness Guide

DOWNLOAD the Key Financial Data Guide

READ about all of today's guests

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:10 - The American College of Financial Services and The Horizons Conference with George Nichols III, CAP®

03:59 - What is the Future of Your Social Security Under the New Administration?

13:11 - Watch Are You Ready to Retire? on YMYW TV and Download the Retirement Readiness Guide

14:05 - Should We Bother Saving for Retirement? We're Inheriting $20M. (Lucy & Ricky, WI)

19:05 - When to Claim Social Security? Should I Do Roth Conversions? Medicare vs. Advantage? (Tybob, AZ)

23:28 - I'm 50 With $2.4M Saved. Should I do 72(t) Tax Elections and Retire Right Now? (Speedy Racer, North GA)

33:12 - Download the Key Financial Data Guide for free

34:30 - Comment: Your Podcast Is Impactful for the "Gilligans" (Gilligan, NY)

40:48 - Next Week on the YMYW Podcast

Haven't Yet Saved a Million. Can We Still Retire Early? - 520 Mar 11, 2025

Martin and Caterina in Green Bay are in their 40s and haven't yet saved a million bucks. Are they on track to retire at age 58? Can Piggie and Kermit in California retire today at ages 50 and 57 and still build wealth for their children? Can Galahad and Zoot in Chicago retire early in their 50s, or do they need to keep working? Do Bo and Daisy have enough saved to retire now at 61 and 56? Plus, Chuck in South Carolina asks, if you can retire early, why wouldn't you? Spitballing early retirement, today on Your Money, Your Wealth® podcast 520 with Joe Anderson, CFP® and Big Al Clopine, CPA.

Free financial resources & episode transcript: https://bit.ly/ymyw-520

WATCH this episode on YouTube

WATCH Don't Make These 10 Will and Trust Mistakes on YMYW TV

DOWNLOAD the Estate Planning Organizer

CALCULATE your Financial Blueprint

ASK Joe & Big Al for your Retirement Spitball Analysis

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:48 - In Our 40s and Haven't Hit a Million Yet. Are We On Track for Retirement? (Martin & Caterina, Green Bay - voice)

10:29 - We Have Over $5M. Can We Retire Today at 50 and 57 and Still Build Wealth for Our Kids? (Piggy & Kermit, CA)

18:24 - Watch 10 Will and Trust Mistakes to Avoid on YMYW TV and Download the Estate Planning Organizer

19:08 - We're 56 and 52 With $500K. Can I Retire Early at 62? (Galahad and Zoot, Chicago)

25:36 - We're 61 and 56 With $600K. Have We Saved Enough for Retirement? (Bo & Daisy, upstate NY)

33:49 - Calculate Your Financial Blueprint

34:12 - We're 61 and 58 With $1.5M. How Much Can We Spend in Retirement, When Should We Claim Social Security? (Hefwannabe and Jane, OK)

42:19 - If You Can Retire Early, Why Wouldn't You? (Chuck, SC)

48:11 - YMYW Podcast Outro

What's a Safe Withdrawal Rate in Retirement? (So You Won't Run Out of Money) - 519 Mar 04, 2025

How much do Nick and Nora in Pittsburgh, and Doc Mc Muffin and her Mr. in Minnesota, need to have saved, and how much can they afford to spend in retirement? What are the disadvantages to Fred and Ethel in Virginia if Ethel collects her Social Security early? Are the Moonshiner and the City Girl in Florida so obsessed with avoiding RMDs and IRMAA that they're wasting too much savings on Roth conversions? That's today on Your Money, Your Wealth® podcast 519 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, will the tax benefits on a rental property offset the negative cash flow for Lily's 29-year-old son, who has started his professional career with a $750K salary?

Free financial resources & episode transcript: https://bit.ly/ymyw-519

DOWNLOAD the Withdrawal Strategy Guide for free

LIMITED TIME OFFER: Download the Money Makeover Guide by this Friday, March 7! Watch Complete Money Makeover: How to Do a Financial Facelift on YMYW TV

YMYW Accolades on Feedspot and Goodpods

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

SUBSCRIBE to YMYW on YouTube

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:51 - How Much Should We Have Saved Before Retirement? (Nick & Nora, Pittsburgh, PA)

12:01 - Download the Withdrawal Strategy Guide for free

12:38 - We're 40 with $2.7M Saved. Spitball on What We're Missing. (Doc McMuffin, MN)

18:40 - Any Disadvantages to Claiming Social Security Early? (Fred & Ethel, VA)

26:11 - Am I Overly Obsessed with Reducing RMDs and IRMAA, Wasting too Much on Roth Conversions? (The Moonshiner and the City Girl, Orange Park, FL)

34:52 - LIMITED TIME OFFER: Download the Money Makeover Guide by this Friday, March 7! Watch Complete Money Makeover: How to Do a Financial Facelift on YMYW TV

35:36 - Son Makes $750K. Will Rental Property Tax Benefits Offset Negative Cash Flow? (Lily, CA)

40:32 - Joe and Big Al's Very First Jobs

44:18 - YMYW Accolades on Feedspot and Goodpods

Should You Switch Retirement Contributions to Roth? - 518 Feb 25, 2025

Is it better to save for retirement in traditional 401(k)s and IRAs, or in Roth accounts? That's today on Your Money, Your Wealth® podcast 518 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, what are the rules around contributing to two different types of Roth accounts? If required minimum distributions will be staggered because of a couple's age difference, should they convert their retirement savings to Roth, or leave it alone? But first, Joe and Big Al have a backdoor Roth conversion withdrawal debate to settle.

Access free financial resources and the episode transcript: https://bit.ly/ymyw-518

DOWNLOAD The Ultimate Guide to Roth IRAs for free

WATCH Will Your Money Last Through Retirement? on YMYW TV

DOWNLOAD The Retirement Lifestyles Guide for free

WATCH Is a Market Correction Coming in 2025? Q&A and Feedback (YouTube Exclusive)

ASK Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE your Free Financial Assessment

SUBSCRIBE to YMYW on YouTube

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:02 - Can Backdoor Roth Conversions Be Withdrawn at Any Time? (Tyler, Arlington, VA)

06:11 - Am I Allowed to Have Two Roth Accounts? Should I Use My Roth 403(b)? (Kimberly, NY)

07:06 - Should I Switch Contributions from Traditional TSP to Roth? (Kate, Cleveland, OH)

11:47 - Download the Ultimate Guide to Roth IRAs for free

12:43 - Self-Insuring Long-Term Care: Traditional IRA or Roth? (Neo, San Clemente, CA)

18:05 - Our RMDs Will Be Staggered. Should We Convert $4M to Roth or Leave It Alone? (Mike, Western PA)

22:00 - Should I Switch Traditional IRA Contributions to Roth? (Joe, NC)

25:39 - Watch Will Your Money Last Through Retirement? on YMYW TV, Download the Retirement Lifestyles Guide for free

26:31 - Should We Dial Back Pre-Tax Savings and Put More in Brokerage? (Herc & Angel, MA)

31:44 - We Can Mega-Save. What's Our Plan of Attack? Ricky Bobby, Charlotte, NC)

38:42 - Watch "Is a Market Correction Coming in 2025? YMYW Podcast Q&A and Feedback" (YouTube Exclusive)

0% Capital Gains Tax vs. Roth Conversion vs.... a Cruise? - 517 Feb 18, 2025

Should Nancy in Washington take out a 401(k) loan and invest it in her brokerage account to catch up on saving for her retirement? When Joe and Big Al talk about having a balanced portfolio of various asset classes like stocks and bonds, Brian in Naperville, Illinois wonders whether that asset allocation strategy takes into account the stabilizing effect of monthly Social Security payments? That's today on Your Money, Your Wealth® podcast 517 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Joy and her brother are each inheriting $400,000. How should they each invest it for their very different financial situations? Mike in Colorado has a good guaranteed income stream, so what should he do with the money he's drawing from his taxable IRA every year - convert to Roth, put it in a brokerage account, go on a cruise? And finally, Skipper asks the fellas to spitball on whether he should do Roth conversions or take advantage of zero percent capital gains tax rates. Access free financial resources and the episode transcript: https://bit.ly/ymyw-517

DOWNLOAD the free Retirement Income Strategies Guide

REGISTER for the free Risk Management and Retirement Planning webinar, Wednesday, February 26, 12pm Pacific / 3pm Eastern

WATCH Retirement Rebound: 5 Plays to Help You Score a Comeback on YMYW TV

ASK Joe & Big Al for your Retirement Spitball Analysis

CALCULATE your free Financial Blueprint

SCHEDULE your Free Financial Assessment

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Mutual Funds vs. ETFs, Bonds to Bourbon - 516 Feb 11, 2025

What are the benefits and differences between exchange-traded funds and mutual funds? Mike in Colorado wants to know. How should Lauren in Florida approach the fixed-income portion of her investment portfolio? Would a balanced fund be good for asset allocation in the decumulation phase for DJ in Missouri? Plus, Karen wants to make a one-time roulette investment. Should she hire a broker or do it herself? Joe Anderson, CFP® and Big Al Clopine, CPA spitball on investing from the basics to the alternatives, today on Your Money, Your Wealth® podcast number 516. But first, something for YMYW's legion of Old-Fashioned drinkers: find out how you can put your money where your mouth is with our special guest Jeremy Kasler, the founder and CEO of CaskX, making investing in whiskey and bourbon more accessible and transparent for investors.

Access free financial resources and the episode transcript: https://bit.ly/ymyw-516

DOWNLOAD The Investing Basics Guide

WATCH Financial Facts vs. Fiction: The Truth May Shock You! on YMYW TV

DOWNLOAD The Retirement Readiness Guide

WATCH the full interview with Jeremy Kasler of CaskX

ASK Joe & Big Al for your Retirement Spitball Analysis

CALCULATE your free Financial Blueprint

SCHEDULE your Free Financial Assessment

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:55 - How to Invest in Bourbon and Whiskey with Jeremy Kasler, Founder and CEO of CaskX (watch the full interview exclusively on YouTube)

12:17 - Watch Financial Fact vs. Fiction: The Truth May Shock You! On YMYW TV, Download the Retirement Readiness Guide

13:09 - Big Al and Joe's Favorite Bourbons or Whiskeys

15:17 - ETFs vs. Mutual Funds Explained (Mike, CO)

18:34 - Bonds, Bond Funds, TIPs, CDs: Where to Invest for Fixed Income? (Lauren, FL)

21:47 - Download the Investing Basics Guide, Calculate your Free Financial Blueprint

22:54 - Is a Balanced Fund Good for Asset Allocation in the Decumulation Phase? (DJ, Missouri)

27:33 - One-Time Roulette Investment: Should I Hire a Broker or Do It Myself? (Karen)

31:46 - Outro: Next Week on the YMYW Podcast

Financial Planning for Marriage, Separation, and Singlehood - 515 Feb 04, 2025

Financially speaking, should Old Bear in Northern Kentucky marry his Honey? How should Sebastian in Virginia navigate the financial aspects of his separation? That's today on Your Money, Your Wealth® podcast 515 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Famous Missourians want to know, how much is enough for retirement, and when can you take your foot off the gas? Can Paul with the Big Wallet Bridge the long gap between retiring and claiming Social Security benefits? And can Aspiring Adventurer in Oregon retire single at age 58?

Access free financial resources and the episode transcript: https://bit.ly/ymyw-515

DOWNLOAD The Going Solo Guide for free

WATCH: Going Solo: Navigating Your Financial Future Single on YMYW TV

ASK Joe & Big Al for your Retirement Spitball Analysis

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:44 - Financially Speaking, Should Old Bear Marry His Honey? (Northern Kentucky, near Cincinnati, OH)

08:20 - Navigating Finances When Separating from Your Spouse (Sebastian, VA)

14:52 - Watch Going Solo: Navigating Your Financial Future Single on YMYW TV, Download the Going Solo Guide for free

15:22 - How Much is Enough for Retirement? When Can We Take Our Foot Off the Gas? (JC Penney & Laura Ingalls Wilder, Kansas City, MO)

28:10 - How to Bridge the Long Gap Between Retirement and Social Security (Paul with the Big Wallet)

38:29 - Calculate your free Financial Blueprint

39:00 - Can I Retire at Age 58? Where to Save? Should I Do a Roth Conversion Ladder in Retirement? (Aspiring Adventurer, OR)

50:49 - YMYW Podcast Outro

Deferred Comp, Roth Strategies, Asset Protection (and Gold) - 514 Jan 28, 2025

Mike and his wife in Tampa are 39 and 36, they've got nearly a million bucks saved. Are they on track for retirement? Kate in California is 55 and hopes to retire in the next couple of years. How should she manage deferred compensation and retirement withdrawals? That's today on Your Money, Your Wealth® podcast number 514 with Joe Anderson, CFP®, and Big Al Clopine, CPA. Plus, Joe and Big Al answer questions from our YouTube viewers on considering IRMAA when making Roth conversions, paying Roth conversion taxes quarterly or in December or in January, protecting a gifted house from a child's ex, and the tax impact of rebuilding on an inherited property. Finally, 8 years ago, Joe and Big Al said you shouldn't have more than 2% of your portfolio in gold and one YouTube viewer said that did not age too well. What do the fellas think today? We'll find out.

Access free financial resources and the episode transcript: https://bit.ly/ymyw-514

DOWNLOAD the Cruising Into Retirement Checklist and Guide

WATCH How to Cruise Into Your Retirement on YMYW TV

DOWNLOAD the Withdrawal Strategy Guide for free

ASK Joe & Big Al for your Retirement Spitball Analysis

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:56 - 39 & 36 With Nearly $1M. How Are We Doing? (Mike, Tampa, FL)

07:30 - Watch How to Cruise Into Your Retirement on YMYW TV, Download the Cruising Into Retirement Checklist and Guide by Friday, Jan. 31, 2025!

08:14 - Hoping to Retire in the Next Couple of Years. How Should I Manage Deferred Comp and Withdrawals? (Kate, CA, 55)

16:23 - Download the Withdrawal Strategy Guide for free

16:56 - Roth Conversions Prior to IRMAA for Alex in podcast 510? (Thomas, YouTube)

18:54 - How to Pay Roth Conversion Taxes Before Filing 2024 Taxes? (PoolMileThirty, YouTube)

21:39 - Paying Roth Conversion Tax in December vs. January (TacticalTruth, YouTube)

22:53 - How To Avoid Child's Ex Taking Half of Gifted House? (Emjay, YouTube)

23:53 - Will Kids Keep Stepped Up Basis If They Build New House on the Property? (Thaigera, YouTube)

27:53 - Gold Doesn't Grow? That Didn't Age Well (Eldon, YouTube comment)

29:39 - Outro: Next Week on the YMYW Podcast

I Work in a Toxic Office. Can I Retire Early? - 513 Jan 21, 2025

Today on Your Money, Your Wealth® podcast 513 with Joe Anderson, CFP®, and Big Al Clopine, CPA, YMYW listeners in their 40s are ready to call it quits at work, become financially independent, and retire early. Can they afford to do it? Peter and Joanna want to retire in the next two years. "Burned Out and Ready to Retire" wants out of his toxic office. If Maryland Chicken Man never earns another dollar, how much can he withdraw from his retirement accounts each year? Plus, Suzanne in Massachusetts is 69 and needs $60K annually for 30 years. Is she all right?

Access free financial resources and the episode transcript: https://bit.ly/ymyw-513

DOWNLOAD the 2025 Key Financial Data Guide for free

WATCH 10 Big Retirement Regrets to Avoid (Before It's Too Late) on YMYW TV

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SCHEDULE your Free Financial Assessment

ASK Joe & Big Al for your Retirement Spitball Analysis

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:09 - We're 45 and 44. Can We Retire in the Next 2 Years? (Peter & Joanna, NJ)

10:24 - Watch 10 Big Retirement Regrets to Avoid (Before It's Too Late) on YMYW TV, Calculate your Free Financial Blueprint

11:23 - I'm 42 and I Work in a Toxic Office. Can I Afford to Retire? (Burned Out and Ready to Retire, NJ)

21:53 - Download the 2025 Key Financial Data Guide for free

22:32 - I'm 69 and Need $60k/Year for the Next 30 Years. Am I All Right? (Suzanne, MA)

25:19 - I'm 45. If I Never Earn Another Dollar How Much Can I Withdraw Every Year? (Maryland Chicken Man)

34:54 - Outro: Next Week on the YMYW Podcast

Choosing the Right Investments for You - 512 Jan 14, 2025

What is the risk with BDCs, or business development company funds? Edward in Illinois wants to know. Do Pebbles and Bam Bam in Kentuckystone have too much invested in T-bills? Are mutual funds or ETFs a better place for them to invest qualified money in the decumulation phase? Is there a difference between a traditional IRA and a rollover IRA? And Keith in Connecticut is 34 and wants a spitball on whether his investments are appropriate for his time horizon, today on Your Money, Your Wealth® podcast number 512 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Gus in Philly needs a withdrawal strategy for his dad's multi-year guaranteed annuities (MYGAs). Speaking of MYGAs, YouTube viewer Ken thinks everyone should invest in MYGAs and bonds, and nobody should ever pay a financial advisor. What do Joe and Big Al think? And finally, comments on your state of residence for tax purposes from Greg, the prorated sale of a primary residence, and bonds vs. pension from Keith, and 7SideWays tells the fellas to focus on PERMA already - but what is it?

Access free financial resources and the episode transcript: https://bit.ly/ymyw-512

LIMITED TIME OFFER: DOWNLOAD The DIY Retirement Guide before the Special Offer changes on Friday January 17, 2025!

SCHEDULE your Free Financial Assessment

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Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:09 - What's the Risk with Business Company Development (BDC) Funds? (Edward, IL)

04:04 - T-Bills, Decumulation, IRAs, and Investing Strategies (Pebbles & Bam Bam, Kentuckystone)

11:21 - LIMITED TIME OFFER: Download the DIY Retirement Guide by Friday, Jan 17, 2025!

12:24 - I'm 34. Are My Investments Appropriate for My Time Horizon? (Keith, CT)

18:22 - Multi-Year Guaranteed Annuity (MYGA) Retirement Withdrawal Strategy for Dad (Gus in Philly)

22:34 - Just Buy MYGAs and Bonds and Don't Pay an Advisor (comment from Ken, YouTube)

27:36 - Schedule a Free Financial Assessment with Pure Financial Advisors, Learn More about Pure's Fees and Services

28:47 - State Taxes vs. State of Residency (comment from Greg, Temecula)

30:17 - Favor Questions from People with Less than $6M Please (comment from Ed, YouTube)

31:08 - Prorated Sale of Primary Residence (comment from Keith, YouTube)

33:01 - $1M Bonds vs. $40K/yr Pension (comment from Keith, YouTube)

34:54 - Focus on PERMA Already (comment from 7SideWays, YouTube)

36:11 - YMYW Podcast Outro

Grow Your Wealth Tax-Free & Retire Sooner: YMYW Best of 2024 - 511 Jan 07, 2025

YMYW friends, welcome to 2025. Today on Your Money, Your Wealth® podcast number 511, we're revisiting your favorite topics of 2024 as Joe Anderson, CFP® and Big Al Clopine, CPA spitball on strategies for building up tax-free retirement income in Roth accounts, determining your appropriate mix of taxable, tax-deferred, and tax-free savings (also known as tax diversification), and whether YMYW viewers and listeners can retire as soon as possible.

Access free financial resources and the episode transcript: https://bit.ly/ymyw-511

DOWNLOAD the 2024 Key Financial Data Guide for free

CALCULATE your Free Financial Blueprint

SCHEDULE your Free Financial Assessment

ASK Joe & Big Al for your Retirement Spitball Analysis

SUBSCRIBE to YMYW on YouTube

DOWNLOAD more free guides

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WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

LISTEN to the Best of the YMYW Podcast 2021, 2022, 2023

LISTEN to the Top Funniest Moments from the YMYW Podcast Vol. 1, Vol. 2

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast
00:59 - Can We Afford to Spend $120k/Year Inflation Adjusted in Retirement? (Joe & Angelina Jolie, Strawberry Plains, TN)
- From ep. 503: YMYW Most Plays in 2024 on Apple Podcasts, YMYW Most Streamed in 2024 on Spotify
08:14 - Can I Contribute to My Wife's Roth IRA? Can I Max Out Multiple Roth Accounts? Should We Do Roth Conversions? (Theodore & Louise, Seattle, WA)
- From ep. 504: YMYW Most Consumed in 2024 on Apple Podcasts, YMYW Most New Subscribers in 2024 on YouTube
15:21 - Download the 2024 Key Financial Data Guide for free. Subscribe to the YMYW podcast, the YouTube channel, and the YMYW newsletter, and get the 2025 guide as soon as it's released!
16:46 - We Want to Retire As Soon as Humanly Possible. Brokerage vs. Solo 401(k) for Surplus Funds? (Ricochet J, CO)
- From ep. 505: YMYW Most Engaged Listeners in 2024 on Apple Podcasts, YMYW Most Listeners in 2024 on Spotify
31:05 - How Much Money Do We Need to Retire ASAP? (Barney and Betty, NE New Jersey)
- From ep. 493: YMYW Most Engaged Listeners in 2024 on Amazon Music
44:20 - Calculate your Financial Blueprint, Schedule a Financial Assessment
45:39 - Ed Slott: How Much Money Can You Save in Taxes With Good Tax Planning? What About People Who Don't Have the Money to Pay the Tax on a Roth Conversion?
- From ep. 489: YMYW Most Views & Watch Time in 2024 on YouTube
51:51 - Tax Diversification General Guidelines? (Brian, Naperville, IL)
- From ep. 468: YMYW Most Downloaded Across All Podcast Platforms in 2024
57:33 - Andi's Favorite Derail of 2024: Clark & Ellen Griswold, Tuktoyaktuk reading Derail from ep. 498
1:01:07 - Outro: 2024 YMYW Podcast Stats

Defusing a Future Tax Bomb With Roth Conversions - 510 Dec 31, 2024

Does it make sense for Alex and his wife in Massachusetts to do Roth conversions now to the top of their eventual tax bracket? Steve in San Diego got serious about saving for retirement after Joe and Big Al gave him some tough love 5 years ago. Is he good to retire now, and should he convert to Roth? That's today on Your Money, Your Wealth® podcast number 510 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, can Barbara in New Jersey's grandson move excess 529 funds to a Roth and withdraw the money after 5 years? PWare has a cunning plan to gift appreciated stock to avoid capital gains tax, but will it work? Should Mike create a limited liability company for his rental properties? And finally, qualified charitable distributions don't make sense to GetSmart Paul. Sherri in California wonders if her kids can inherit her savings account without any tax penalty, and whether there's a safe, high-yielding investment she should put it in. And Houry in New York wonders if her IRA can fund a charitable remainder unitrust, or CRUT.

Access free financial resources and the episode transcript: https://bit.ly/ymyw-510

DOWNLOAD The Complete Roth Papers Package

DOWNLOAD The Retirement Readiness Guide

WATCH Retirement Pop Quiz: 18 Questions to Get You Ready to Retire on YMYW TV

LISTEN to Steve in San Diego's 2019 question

Al: "Maybe you gotta live in a trailer somewhere." Joe: "that side hustle, you better be able to do that in a wheelchair."

LISTEN to YMYW Podcast Best of 2021, 2022, and 2023

REQUEST: Ask Joe & Big Al for your Retirement Spitball Analysis

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SUBSCRIBE: YMYW Newsletter

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:08 - Should We Do Roth Conversions to Our Eventual Tax Bracket? (Alex, MA)

07:51 - YMYW Tough Love Made Me Get Serious. When Can I Retire? Should I Do Roth Conversions? (Steve, San Diego, CA)

14:11 - Download the Complete Roth Papers Package for free

14:59 - Can Grandson Withdraw 529 Funds From Roth After 5 Years? (Barbara, NJ)

18:37 - Can We Avoid Capital Gains Tax With This Appreciated Stock Gifting Strategy? (P Ware)

20:57 - Should I Create an LLC for Rental Properties? (Mike, voice)

23:00 - Qualified Charitable Distributions Don't Make Sense to Me (GetSmart Paul, YouTube)

24:59 - Watch the Retirement Pop Quiz on YMYW TV, Download the Retirement Readiness Guide for free

25:45 - Do My Kids Inherit My Savings Account Without Tax Penalty? What's a Safe, High-Return Investment for Them? (Sherri, CA)

27:18 - Can an IRA Fund a Charitable Remainder Unitrust? (Houry, NY)

31:43 - Outro: Next Week on the YMYW Podcast

When to Claim Social Security and the Truth About Annuities - 509 Dec 24, 2024

When should Richie and Heather and Rebecca and Sam collect their Social Security benefits? Why is Dan's benefit so much higher than his wife's? PWare has a Roth conversion case for claiming Social Security AFTER age 70, and Jerry wonders how Donald Trump's plan to stop taxing Social Security could impact claiming strategies. Plus, Joe rants about Rebecca and Sam's $1 million single premium deferred indexed annuity, and the fellas also spitball on their Roth conversion and retirement strategy and how much is too much when it comes to paying advisor fees. Access free financial resources and the episode transcript: https://bit.ly/ymyw-509

DOWNLOAD the Social Security Handbook

CALCULATE your free Financial Blueprint online

SCHEDULE your free Financial Assessment with an experienced professional

Ask Joe & Big Al for your Retirement Spitball Analysis

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READ: financial blogs

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SUBSCRIBE: YMYW Newsletter

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:00 - When Should We Take Social Security? Should We Convert Our IRAs to Roth? (Richie & Heather, ID - voice)

09:04 - Download the Social Security Handbook

10:01 - What Should I Do With a $1M Single Premium Deferred Indexed Annuity? When Should We Take Social Security? Is 2% Advisor Fee Excessive? (Rebecca and Sam, VA)

28:03 - Calculate your Financial Blueprint online, Schedule an Assessment with a financial professional

29:25 - Why Is My Spouse's Social Security Benefit So Much Lower Than Mine? (Dan)

30:51 - The Roth Conversion Case for Drawing Social Security After Age 70 (P Ware, YouTube)

36:55 - Would Tax-Free Social Security Income Impact Claiming Strategies? (Jerry, Phoenix, AZ)

42:08 - Outro: Next Week on the YMYW Podcast

Bonds and Annuities, Social Security and Retirement Spending - 508 Dec 17, 2024

John in Pennsylvania doesn't have bonds in his investment portfolio. Should he add them, and if so, where? That's today on Your Money, Your Wealth® podcast number 508 with Joe Anderson, CFP® and Big Al Clopine, CPA. The fellas also spitball on retirement plans for James in Tierrasanta, California, who has $4 million plus annuities, Esther in the San Francisco Bay Area, who has nearly $12M net worth, and Tiger and Lioness, who wonder about a safe level of lifestyle creep. Also, Charlie in Castlerock, Colorado has an "exciting" new question on how to balance collecting Social Security with making withdrawals from his pre-tax retirement account for living expenses. And a Worrywart Mom in Seattle asks whether her 27-year-old daughter should focus on paying off her student loans or saving for the future.

Access all the following free financial resources and the episode transcript: https://bit.ly/ymyw-508

DOWNLOAD the Retirement Income Strategies Guide

DOWNLOAD the Social Security Handbook

DOWNLOAD the Retirement Readiness Guide

WATCH Retirement Sabotage! on YMYW TV

REQUEST: Ask Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE: free financial assessment

SUBSCRIBE: YMYW on YouTube

DOWNLOAD: more free guides

READ: financial blogs

WATCH: educational videos

SUBSCRIBE: YMYW Newsletter

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:58 - Where Should We Add Bonds in Our Investment Portfolio? (John, PA)

06:58 - Does Our Retirement Spending Plan Work? What's a Safe Level of Lifestyle Creep? (Tiger & Lioness)

13:39 - Download the Retirement Income Strategies Guide for free

14:24 - Collecting Social Security vs. Living Off of Pre-Tax Retirement Withdrawals (Charlie, Castlerock, CO)

21:52 - Download the Social Security Handbook for free

22:27 - Should 27 Year Old Pay Off Student Loan or Save for the Future? (Worrywart Mom, Seattle, WA)

27:01 - I Have $11.8M Net Worth and Want to Retire in 2 Years. Can I Pull This Off? (Esther, SF Bay Area)

32:41 - Watch Retirement Sabotage: 12 Post-Retirement Money Mistakes to Avoid on YMYW TV, download the Retirement Readiness Guide for free

33:40 - We Have $4M + Annuities and Want $180K/Year in Retirement. What Do You Think? (James, Tierrasanta, CA)

39:42 - Outro: Next Week on the YMYW Podcast

9 Answers to Boost Tax-Free Roth Retirement Income - 507 Dec 10, 2024

Joe Anderson, CFP® and Big Al Clopine, CPA spitball on paying the tax on your Roth conversions on Your Money, Your Wealth® podcast number 507. If you take the money out of your retirement account, what does Joe mean that you'll be "paying the tax to pay the tax to pay the tax"? Can you pay it from the Roth account itself, or from your monthly pension tax withholding? Are the fellas wrong on this whole topic altogether? They also spitball on withdrawing Roth 401(k) contributions that were rolled to an IRA, those infamous 5-year rules for withdrawals from Roth accounts, when to do Roth conversions, saving to tax-deferred, taxable, or tax-free accounts, and how long-term capital gains taxes fit into the picture. Plus, consolidating individual stock investments and the fate of the home office deduction, and what Joe thinks about the Apple Podcasts reviewer that says he's checked out.

Access all the free financial resources and the episode transcript: https://bit.ly/ymyw-507

DOWNLOAD The 5 Year Rules for Roth IRA Withdrawals

DOWNLOAD The Withdrawal Strategy Guide

WATCH How to Break Through Retirement Barriers on YMYW TV

CALCULATE your free Financial Blueprint

REQUEST: Ask Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE: free financial assessment

SUBSCRIBE: YMYW on YouTube

DOWNLOAD: more free guides

READ: financial blogs

WATCH: educational videos

SUBSCRIBE: YMYW Newsletter

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:06 - Can I Withdraw Roth 401(k) Contributions That Were Rolled to IRA? (Peter LemonJello, FL)

05:32 - Paying the Tax to Pay the Tax" on Roth Conversions Clarified (David)

09:13 - Should We Save to Tax-Deferred Accounts, Backdoor Roth, or Brokerage? (David & Victoria, Cincinnati, OH)

15:23 - Watch How to Break Through Retirement Barriers on YMYW TV, Calculate Your Free Financial Blueprint

16:17 - Should I Do Roth Conversions at Age 66 If I Want to Retire at 70? (Mike, PA)

17:49 - You're Wrong About Roth Conversion Tax Payments (Robert, YouTube)

20:20 - Can I Pay Roth Conversion Tax From Monthly Pension Withholding? (Big Toe Knee, YouTube)

20:45 - Should I Consolidate Individual Stocks Into ETFs? (Lu, YouTube)

22:44 - Do I Understand the 5-Year Rules for Roth Withdrawals? (NR, YouTube)

25:51 - Download the 5-Year Rules for Roth IRA Withdrawals and the Withdrawal Strategy Guide

26:39 - Was the Home Office Deduction Eliminated Under the Tax Cuts and Jobs Act? (George, YouTube)

27:30 - Contributing to Roth vs. Pre-Tax: Would It Count as Long-Term Capital Gains? (Moriel, YouTube)

30:16 - Is it a Good Idea to Pay Roth Conversion Tax Out of the Roth? (Michelle, Facebook)

31:35 - Joe is Completely Checked Out (Anonymous Apple Podcasts Review)

33:19 - Outro: Next Week on the YMYW Podcast

How to Plan for 35 Years of Retirement Spending With Smart Roth Conversions - 506 Dec 03, 2024

What's a safe withdrawal rate for Wine Guy and Wine Gal in Sonoma California to have 35 years of "guaranteed" retirement spending? How aggressively should they convert their retirement savings to Roth IRA? Should the Bond family move from Silicon Valley to a no-income-tax state in retirement? Can Doc in San Francisco quit work in 8 years when his daughter starts college? Rob in Kansas City and his wife are in their late 30s and have 2 million saved. Can they retire early? Plus, Elisa in Fremont has more than the capital gains exclusion for a married couple of $500,000 worth of home equity. How much will this cost her, and will it kill her IRMAA for Medicare premiums? Should Happy Camper and Jolly Pumpkin take their pension's monthly annuity or the lump sum payout? And finally, Lloyd in South Dakota isn't a fan of retirement accounts and wants Joe and Big Al to talk some sense into him. Access all the free financial resources and the episode transcript: https://bit.ly/ymyw-506

CALCULATE your Financial Blueprint

SCHEDULE your Financial Assessment

WATCH Financial Planning at Every Age on YMYW TV

DOWNLOAD The Retirement Readiness Guide for free

READ THE BLOG: It's Not Too Late! Year-End Financial Moves to Make Right Now

READ THE BLOG: US National Debt and the Impact on Long-Term Investing

REQUEST: Ask Joe & Big Al for your Retirement Spitball Analysis

SUBSCRIBE: YMYW on YouTube

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SUBSCRIBE: YMYW Newsletter

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:05 - What's Our Guaranteed Safe Withdrawal Rate for 35 Years of Retirement? How Aggressive Should We Convert to Roth? (Wine Guy/Gal, Sonoma, CA)

12:09 - Calculate your Financial Blueprint, schedule a Free Financial Assessment

13:45 - Should We Move to a No Income Tax State in Retirement? (James Bond, Silicon Valley, CA - voice)

20:50 - Can I Stop Working in 8 Years When Daughter Starts College? (Doc, San Francisco, CA)

26:10 - Late 30s With $2M. Are We Really on Track for Early Retirement? (Rob, Kansas City)

31:20 - Watch Financial Planning at Every Age on YMYW TV, download the Retirement Readiness Guide

32:25 - Our Home Equity is Over the $500K Exclusion. How Much Will We Be Charged? Will This Kill My IRMAA? (Elisa, Fremont, CA)

35:44 - Should We Take the Monthly Pension or Lump Sum Payout? (Happy Camper & Jolly Pumpkin, WI)

43:03 - I'm Not a Fan of Retirement Accounts. Talk Some Sense Into Me. (Lloyd Christmas, SD)

49:04 - Outro: Read the blogs, It's Not Too Late! Year-End Financial Moves to Make Right Now and US National Debt and the Impact on Long-Term Investing

How to Retire ASAP - and Where to Save to Get There - 505 Nov 26, 2024

Ricochet J in Colorado and her husband want to retire as soon as humanly possible. Are they on track? Should they save their surplus funds to a brokerage account or a solo 401(k)? That's today on Your Money, Your Wealth® podcast 505 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Micah in South Dakota wonders whether having a $40,000 a year pension is basically the same as having a million dollars in bonds, according to the four percent rule. What do Joe and Big Al think? Barney and Betty will be in the 12% or 22% marginal tax bracket, but their effective tax rate will only be between 10% and 12.4%, so how much should they convert to Roth? Are they asking the right question? And finally, Joe and Big Al spitball on ways to ensure that Amir in New Mexico has the maximum possible retirement income to last him to age 90 or 95. Access all the free financial resources and the episode transcript: https://bit.ly/ymyw-505

DOWNLOAD The Complete Roth Papers Package for free

WATCH Your 11-Step Path to Financial Freedom on YMYW TV

CALCULATE your free Financial Blueprint

REQUEST: Ask Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE: free financial assessment

SUBSCRIBE: YMYW on YouTube

DOWNLOAD: more free guides

READ: financial blogs

WATCH: educational videos

SUBSCRIBE: YMYW Newsletter

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:04 - Save to Brokerage vs. Solo 401(k) to Retire as Soon as Humanly Possible? (Ricochet J, CO)

15:23 - Watch Your 11 Step Path to Financial Freedom on YMYW TV, Calculate your free Financial Blueprint

16:36 - Is a $40K/yr Pension Similar to $1M in Bonds According to the 4% Rule? (Micah, SD)

18:48 - Marginal vs. Effective Tax Rates: How Much to Convert to Roth? (Barney & Betty)

22:58 - Download the Complete Roth Papers Package

23:48 - How to Have Maximum Possible Retirement Income to Age 90-95? (Amir, NM)

30:13 - Outro - Next Week on the YMYW Podcast

Rules for Inheritances and Making Roth Contributions for Others - 504 Nov 19, 2024

Can Ted and Georgette convert $1.6M in an inherited trust to Roth without distributing it? Should the trust own their home so they can use the home equity? Melissa was added as joint owner on her parents' bank accounts after a medical event, but what have they done? Should Ralph and Alice use the required minimum distribution from their inherited IRA to pay Roth conversion taxes? That's today on Your Money, Your Wealth® podcast 504 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, can Theodore contribute to a his wife Louise's Roth IRA? Can Marc make Roth contributions for his grandkids? Also, Joe and Al come up with a very unique way that John may be able to pay the tax on his Roth conversion using his home equity. Access all the free financial resources and the episode transcript: https://bit.ly/ymyw-504

DOWNLOAD by Friday: Top 10 Tax Tips Guide - limited time special offer!

WATCH 10 Tax-Cutting Moves to Make Now - YMYW TV

DOWNLOAD: Identity Theft Guide

WATCH: How to Protect Yourself from Scams: Cybersecurity webinar on demand

REQUEST: Ask Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE: free financial assessment

SUBSCRIBE: YMYW on YouTube

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READ: financial blogs

WATCH: educational videos

SUBSCRIBE: YMYW Newsletter

Timestamps:

00:00 - Intro

01:00 - Can We Convert an Inherited Trust to Roth Without Distributing It? Should the Trust Own Our Home? (Ted & Georgette Baxter, Madison, WI)

10:02 - Watch 10 Tax-Cutting Moves to Make Now on YMYW TV, Download the Top 10 Tax Tips Guide before this Friday!

11:08 - I'm Joint Owner of My Parents' Bank Accounts. What Have We Done? (Melissa, Rockport, TX)

16:35 - Can I Contribute to My Wife's Roth IRA? Can I Max Out Multiple Roth Accounts? Should We Do Roth Conversions? (Theodore & Louise, Seattle, WA)

23:43 - Should We Use Inherited IRA RMD to Pay Roth Conversion Tax? (Ralph & Alice Kramden, SC)

27:35 - Can I Fund Roth IRAs for My Grandchildren? (Marc, Encinitas)

28:40 - Watch the Cybersecurity Webinar on demand, Download the Identity Theft Guide

29:32 - Should We Maximize the 24% Tax Bracket With Roth Conversions This Year and Next? (John)

37:55 - Outro: Next Week on the YMYW Podcast

When to Pay Off Your Home, Retire, and Do Roth Conversions - 503 Nov 12, 2024

When should Jack and Swan in Florida pay off their home, retire, and convert their savings to Roth for lifetime tax-free investment growth? Jennifer in Colorado wonders whether she should take taxes into account when calculating her expenses, and whether she should pay off her home to be debt-free in retirement? That's today on Your Money, Your Wealth® podcast 503 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, should Kevin in Scottsdale collect Social Security in 2025, or postpone and do Roth conversions over the next two years? Should Skipper in Texas do Roth conversions to the top of the 24% tax bracket instead of the 22? And just how closely will Big Brother watch his state of residency if Skipper buys homes in Florida and another location for his retirement? Harry Tasker in Minnesota's wife Helen says he needs to continue working. Is that a true lie? Harry asks Joe and Big Al to spitball on whether he and Helen can stay home during their go-go years. And can the Tomb Raiders afford to spend $120,000 a year in retirement? Access free financial resources and the episode transcript: https://bit.ly/ymyw-503

WATCH ON YOUTUBE: https://youtu.be/Xfl7gvIs2rU

DOWNLOAD: Social Security Handbook for free

CALCULATE: Your Financial Blueprint for free

WATCH: 6 Secrets to Bigger Tax Savings from Your Nonprofit Donations on YMYW TV

DOWNLOAD: Tax-Smart Charitable Giving Guide for free

REQUEST: Ask Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE: free financial assessment

SUBSCRIBE: YMYW on YouTube

DOWNLOAD: more free guides

READ: financial blogs

WATCH: educational videos

SUBSCRIBE: YMYW Newsletter

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

01:16 - When to Pay Off the Home, Retire, and Do Roth Conversions? (Jack & Swan, FL - voice)

06:10 - Should We Include Taxes in Annual Expenses? (Jennifer, CO)

09:47 - Draw Social Security in 2025, or Postpone and Convert to Roth in 2025 and 2026? (Kevin, Scottsdale, AZ)

14:57 - Download the Social Security Handbook, Calculate Your Financial Blueprint

16:08 - Should We Pay Off the House to Be Debt Free in Retirement? (Jennifer, CO)

21:08 - State Tax Spitball: Should I Convert Even More to Roth? Does Big Brother Really Count the Days for State Residency? (Skipper, TX)

29:54 - Watch 6 Secrets to Bigger Tax Savings from Your Nonprofit Donations on YMYW TV, Download the Tax-Smart Charitable Giving Guide

30:39 - Can We Both Stay Home in the Go-Go Years? Wife Says I Have to Go Back to Work (Harry & Helen Tasker, MN)

43:40 - Can We Afford to Spend $120k/Year Inflation Adjusted in Retirement? (Tomb Raiders, Strawberry Plains, TN)

51:29 - Outro: Next Week on the YMYW Podcast

Spitballing Early Retirement for the One Percenters - 502 Nov 05, 2024

Can Bauer in Illinois retire at age 57, and when should he collect Social Security? More importantly, can he afford a $300,000 motor home? Can Brad in Michigan coast for the next 10 years and still reach the promised land of retirement somewhere around age 53? Joe Anderson, CFP® and Big Al Clopine, CPA spitball early retirement, today on Your Money, Your Wealth® podcast 502. Plus, it seems weird to Elizabeth in Connecticut that nearly all of her $5M is in taxable accounts. Is that good or bad? N&N in San Francisco Bay Area have $10 million liquid. Should they make Roth contributions and Roth conversions now, or wait until they retire? Access free financial resources and the episode transcript: https://bit.ly/ymyw-502

WATCH: How to Avoid Wealth Busters on YMYW TV

DOWNLOAD the Wealth Busters to Avoid Guide

CALCULATE your Financial Blueprint for free

REQUEST: Ask Joe & Big Al for your Retirement Spitball Analysis

SCHEDULE: free financial assessment

SUBSCRIBE: YMYW on YouTube

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READ: financial blogs

WATCH: educational videos

SUBSCRIBE: YMYW Newsletter

Timestamps:

00:00 - Intro: This Week on the YMYW Podcast

00:58 - Can I Retire at 57? When to Collect Social Security? Can I Afford a Motorhome? (Bauer & Laney, Mundelein, IL - voice)

07:47 - Can We Coast and Still Reach the Retirement Promised Land in Ten Years? (Brad, MI)

14:20 - Watch How to Avoid Wealth Busters on YMYW TV, download the Wealth Busters to Avoid Guide

15:00 - We've Got $10M Liquid: Roth Contributions & Conversions Now or Wait Until Retirement? (N&N, SF Bay area)

24:58 - Calculate Your Free Financial Blueprint

25:36 - Seems Weird That Our Money is in Taxable Accounts. Is That Good or Bad? (Elizabeth, CT)

31:57 - Outro: Next Week on the YMYW Podcast

How to Reduce the Widow's Tax Penalty - 501 Oct 29, 2024

Should Suzanne in Michigan do Roth conversions in 2025 and 2026 since she's widowed and won't be married filing jointly? How should she pay the tax on her conversions? Jennifer in Washington state is 55 and her husband is 70. Should she retire now and do aggressive Roth conversions before her husband passes? We're talking about the widow's tax, today on Your Money, Your Wealth® podcast number 501 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, answers to questions from our YouTube viewers: what's a brokerage account? What's a good way to pay required minimum distirbution taxes? How does the 10 year rule work on inherited IRAs? What are extended market index funds? The fellas also spitball on the 4% rule for retirement withdrawals. Access all the free financial resources and the episode transcript: https://bit.ly/ymyw-501

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Top Funniest Moments From the Your Money, Your Wealth Podcast, Vol. 2 - Ep. 500 Oct 22, 2024

For 499 episodes of YMYW, Joe Anderson, CFP® and Big Al Clopine, CPA have been making fun of finance. On episode 500, we're celebrating The Top Funniest Moments From the Your Money, Your Wealth® Podcast, Vol. 2. (Check out episode 300 from way back in November of 2020 for Vol. 1.) For this episode, Executive Producer Andi Last compiled some rare, never before seen, can't-miss Derails, jokes, stories, screw-ups, and outtakes... from two talking heads sitting at a desk. We appreciate you following, watching, laughing, and commenting on YouTube or Spotify, but if you're listening in Apple Podcasts or another podcast app you'll laugh just as much. Access all the free financial resources and the episode transcript: https://bit.ly/ymyw-500

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00:00 - Intro 00:51 - How to Ask Joe and Big Al On Air 01:20 - More Funnier 03:06 - Making Fun of Finance 08:06 - Don't Change a Thing 09:13 - Spitballing, Not Advice 09:41 - Watch Recipe for Retirement on YMYW TV 10:32 - Story Time: Al's Mid-life Crisis, Al's VW Rabbit, Joe's Travel Experiences, Hans' Paintings, Joe the Player, Joe the Dancer, Color Me Badd, Ricky Runs Fast, You're a 1099, FIRE, Retirement Planning Dinners, Movie Talk, RVO, Joe vs. the Holidays, Ice Skating 35:10 - Joe and Big Al... Are Human 39:56 - Calculate Your Financial Blueprint, Schedule a Free Financial Assessment 41:22 - More Joe and Big Al... Are Human 46:32 - Outro 47:05 - The YMYW Family 48:24 - The Biggest Derail Ever

How to Get Into Real Estate Investing, Spitballing Retirement - 499 Oct 15, 2024

Are real estate investment trust (REIT) ETFs a good way for Leon to begin investing in real estate? Can AI Seth stay retired at age 52, and should he do Roth conversions? Jenn in Ohio wants the fellas to be brutally honest about whether she should move with work, take a break, or retire now. And "George and Weezy" are in their mid-50s - can they "move on up" to a deluxe retirement lifestyle in 2026, or even earlier? That's all today on Your Money, Your Wealth® podcast 499 with Joe Anderson, CFP® and Big Al Clopine, CPA. Access free financial resources and the episode transcript: https://bit.ly/ymyw-499

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00:00 - Intro: This Week on the YMYW Podcast

00:47 - Are REIT ETFs a Good Way to Get Into Real Estate Investing? (Leon, Chicago - voice)

09:15 - Watch Steps to Financial Success: Grow Your Wealth at Any Age on YMYW TV, Download the Guide to Growing Your Wealth

09:49 - Can AI Seth Stay Retired at Age 52? Should He Do Roth Conversions? (Montana, voice)

16:41 - Move With Work, Take a Break, or Retire Now? Be Brutally Honest (Jenn, OH)

21:23 - Calculate Your Financial Blueprint, Schedule a Financial Assessment - both free!

22:02 - Deferred Comp: Can "George and Weezy" Retire in 2026 or Earlier? (IL)

33:18 - Outro: Next Week on the YMYW Podcast

Spend RMDs, or Reduce Distributions and Taxes With Roth Conversions? - 498 Oct 08, 2024

Hawkeye and Elle are age 61 and in the 32% tax bracket. How should they get money into their Roth accounts for tax-free retirement income? Clark and Ellen are 69 and 68, expenses will pretty much be covered by their fixed income, but they'd like to leave Roth money to their kids. Should they keep converting to Roth, or use required minimum distributions for their living expenses? Tom and his wife are 73, and fixed income will cover their retirement spending too. Is it advantageous to them to make three huge Roth conversions beyond their marginal tax bracket to reduce future RMDs? Should they keep things simple by leaving their money in an S&P 500 Index Fund? That's today on Your Money, Your Wealth® podcast 498 with Joe Anderson, CFP® and Big Al Clopine, CPA. Access all the following free financial resources and the episode transcript: https://bit.ly/ymyw-498

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00:00 - Intro: This Week on the YMYW Podcast 01:05 - Tax-Free Roth Strategy When in the 32% Tax Bracket? (Hawkeye & Elle Woods, Atlanta) 12:28 - Limited Time Special Offer: Download the DIY Retirement Guide before the Special Offer changes on Friday, Oct 11 13:31 - Spitball on Roth Conversions vs. RMDs, And Should We Buy More Bonds? (Clark & Ellen Griswold, State College, PA) 27:16 - Calculate a Free Financial Blueprint, Learn About Pure's Financial Assessment 28:36 - Should We Do 3 Huge Roth Conversions to Reduce Future RMDs? (Tom, Las Vegas) 37:59 - Outro: Next Week on the YMYW Podcast

Tax-Savvy In-Plan Roth Conversions and Inherited IRA Withdrawals - 497 Oct 01, 2024

Should David in Ohio use 457 funds to do an in-plan Roth conversion in his 403(b) plan, and should he hire a financial advisor? Chris in DC needs a retirement and Roth conversion spitball analysis, and he needs help getting out of a variable annuity. Kim is anxious that she made a mess of her finances and she wonders how much she should convert to Roth, today on Your Money, Your Wealth® podcast number 497 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, what's the best way for Alissa in Cedar Rapids, Iowa to make tax-efficient withdrawals from an inherited IRA? Access all the following free financial resources and the episode transcript: https://bit.ly/ymyw-497

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Timestamps:

00:00 - Intro: This week on YMYW

00:50 - In-Plan Roth Conversions From 457 to 403(b): Do I Need a Financial Advisor? (David, OH)

10:54 - Get a Free Financial Blueprint, Learn About Pure's Financial Assessment

12:13 - Retirement and Roth Conversion Spitball + How to Get Out of Variable Annuity (Chris, DC)

20:05 - Anxious I Made a Mess of My Finances. How Much Should I Convert to Roth? (Kim)

28:13 - Watch Retirement Rebound: 4 Plays to Score a Comeback on YMYW TV, Download the Retirement Income Strategies Guide

29:08 - Inherited Assets: Best Strategy for Tax-Efficient Retirement Withdrawals? (Alissa, Cedar Rapids, IA)

42:10 - Outro

Age Plus 20 Rule for Retirement Contributions - 496 Sep 24, 2024

How much should you save in pre-tax accounts vs. post-tax accounts? Joe Anderson, CFP® and Big Al Clopine, CPA spitball on the "age plus 20" rule for retirement savings, Roth 401(k) contributions and distributions, and a Social Security claiming strategy for Ralph and Marie in Wilmington, Delaware. Shawn wonders if YMYW listeners are ignoring the WEP and GPO when it comes to Social Security, that is, the Windfall Elimination Provision and the Government Pension Offset. Plus, can Jake and Amy in Iowa retire in 5 years, or do they need to work beyond age 60? Should Edwin stop making Roth contributions and start doing Roth conversions instead? And finally, how can Jeff in North Dakota's son qualify for the American Opportunity Tax Credit? Access all the following free financial resources and the episode transcript: https://bit.ly/ymyw-496

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Timestamps:

00:00 - Intro

01:09 - Roth 401(k) Contributions and Distributions, Age Plus 20 Rule, and Social Security Claiming Strategy (Ralph and Marie, Wilmington, DE)

12:35 - Download the Social Security Handbook, Download the Medicare Check-Up Guide, Watch Medicare Check-Up: How to Keep Your Retirement Plan Off Life Support on YMYW TV, Register for the Medicare Basics webinar Wed. Sept 25, 12P/3E

13:37 - Are Listeners Ignoring Government Pension Offset and Windfall Elimination Provision for Social Security? (Shawn)

17:30 - Can We Retire in 5 Years Or Do We Need to Work After Age 60? (Jake & Amy, Iowa)

26.36 - Financial Blueprint - get your complementary retirement analysis

27:45 - Should I Stop Roth Contributions and Do Roth Conversions instead? (Edwin)

31:24 - American Opportunity Tax Credit for College Age Son (Jeff, ND)

35:58 - Outro

3 Strategies to Pay Roth Conversion Taxes - 495 Sep 17, 2024

Today on Your Money, Your Wealth® podcast 495, Joe Anderson, CFP® and Big Al Clopine CPA spitball on three different listeners' strategies for paying the tax on a Roth conversion now, to have lifetime tax-free growth on that money in the future. Should Neo in San Clemente, California convert to Roth at the beginning or end of the year in his plan to make quarterly estimated tax payments on his conversion? Is it a good strategy for Tim in Minnesota to use reimbursements from his health savings account to pay Roth conversion taxes? And what do Joe and Big Al think of Samantha in Northern California's plan to convert to Roth and pay the tax with her IRA money? Plus, the fellas answer questions from our YouTube and Spotify followers on required minimum distributions from Roth accounts, reasons to put retirement withdrawals in a brokerage account instead of a Roth, choosing pension options, and the difference between commercial annuities and pension annuities. Plus, their thoughts on single premium immediate annuities (SPIA). Access all the following free financial resources and the episode transcript: https://bit.ly/ymyw-495

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Timestamps:

00:00 - Intro

01:02 - Timing of Roth Conversions - and Paying Quarterly Estimated Taxes (Neo, San Clemente)

06:37 - Is Using HSA Reimbursement to Pay Roth Conversion Taxes a Good Strategy? (Tim, MN)

08:44 - Complete Roth Papers Package - free download. Financial Blueprint - free retirement analysis

09:39 - How Is Our Plan to Convert to Roth and Pay the Tax With IRA Money? (Samantha, Northern California)

19:15 - What Happens to Your 401(k) & IRA at Retirement? Watch YMYW TV, download the Retirement Readiness Guide

20:01 - RMDs for Roth Accounts: Clarification for Solo 401k (Andy, YouTube)

21:43 - Joe and Al walk into a bar… (Tony, YouTube)

22:44 - Any Reason to Put Withdrawals in Brokerage Instead of Roth? (Globe Trotter, YouTube)

23:35 - How to Decide Between Pension Options? (Frank, YouTube)

25:40 - Is a Pension Annuity a Bad Thing? (Invictus, YouTube)

26:47 - Are SPIAs the Best Annuity for Lifetime Income? (1212482970, Spotify)

29:23 - Outro

30:58 - The Derails

How to Get Into the Stock Market: Dollar Cost Average or Go All In? - 494 Sep 10, 2024

TJ in Louisiana has been sitting on the sidelines, but now it's time to get into the market. Should he dollar cost average, or just go all in? Margaret in California has an idea of selling a stock at a loss and buying a put option on that stock that expires after the 30-day waiting period. Does this work as a tax loss harvesting strategy? When is it worth it for Brian in Charlotte, North Carolina to diversify beyond a basic three-fund portfolio? Should Christine in San Diego convert her variable annuity to a fixed indexed annuity? That's all today on Your Money, Your Wealth® podcast 494 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, how should Dean in Columbus, Georgia invest inherited retirement money? Are Jen and John on track for retirement, and how should they fund their home remodel? Are there any negative consequences for Steve in Pennsylvania if he finds a new financial advisor just a few months after hiring his current advisor? The fellas also talk through how Chris can give money to charity from his required minimum distributions. And finally, Terry calls in with a follow-up question about whether a solo 401(k) is an option to avoid unrelated business income tax (UBIT). Access all the following free financial resources and the episode transcript: https://bit.ly/ymyw-494

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Timestamps:

00:00 - Intro

01:13 - I Want to Get Into the Market. Dollar Cost Average or Go All In? (TJ, Louisiana)

07:08 - Does This Tax Loss Harvesting Strategy Work? (Margaret, CA)

07:45 - When Is It Worth Diversifying Beyond a Basic Three Fund Portfolio? (Brian, Charlotte, NC)

13:33 - Factor Investing: What Is It? Should You Be Doing It? - Read the blog, Download the Investing Basics Guide and 10 Steps to Improve Investing Success

14:00 - Should I Convert a Variable Annuity to Fixed Index Annuity? (Christine, San Diego)

18:21 - How to Invest Inherited Retirement Funds and Where to Save Extra Money? (Dean, Columbus, GA)

21:50 - How Should We Fund Our Home Remodel? Are We On Track for Retirement? (Jen and John, California)

29:43 - How Your Home Can Create Retirement Income: Watch YMYW TV, Download the Retirement Readiness Guide

30:15 - Solo 401(k) to Avoid Unrelated Business Income Tax (UBIT)? (Terry - voice)

32:31 - Switching to a Fee Only Advisor: Any Negative Consequences? (Steve, PA)

37:19 - Intelligent Charitable Giving Through Qualified Charitable Distributions (Chris)

41:05 - Outro

How Much Money Do You Need to Retire ASAP? - 493 Sep 03, 2024

Can "Alanis" retire early at age 60? With "Barney and Betty's" spending patterns, can they retire ASAP? "Daisy and Donald" need retirement income for 40 years. Can they retire now? That's today on Your Money, Your Wealth® podcast 493 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, we review the results of the 7th Annual YMYW Podcast Survey (congratulations to jemart for winning the Amazon e-gift card!) and Joe and Big Al take on some critical YouTube comments from Keith, following their interview with Ed Slott, CPA.

Access all the following free financial resources and the episode transcript: https://bit.ly/ymyw-493

WATCH: Retirement Pop Quiz on YMYW TV

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Timestamps:

00:00 - Intro

00:57 - Are My Estimates Solid for Early Retirement at Age 60? ("Alanis", WA)

10:39 - Watch Retirement Pop Quiz on YMYW TV and Download the Retirement Readiness Guide

11:20 - How Much Money Do We Need to Retire ASAP? ("Barney and Betty", NE New Jersey)

24:36 - Can We Retire Now? ("Daisy Duck", Emerald City)

30:48 - Subscribe to the YMYW YouTube Channel

31:15 - 7th Annual YMYW Podcast Survey Results

38:54 - Comment: Keith Doesn't Like Ed Slott or Roth Conversions

47:45 - Outro

48:58 - The Derails

Exchange Funds Explained, Roth Conversion Timing - 492 Aug 27, 2024

What is an exchange fund and is it a good thing if you have a lot of capital gains like Bryan in New York? That's today on Your Money, Your Wealth® podcast 492 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, what should be the timing and ordering of Billy Joe and Bobby Sue's Roth conversion strategy to help them achieve 33 years of retirement income? Is Boston overspending or underspending in retirement? Should Andy keep life insurance policies for her kids with ADHD? How does the 5-year rule for Roth withdrawals apply to inherited Roth IRAs for Karen? Visit the show notes for the YMYW Podcast Survey and secret password (only for the next three days!), plus access the free financial resources listed below, and the episode transcript: https://bit.ly/ymyw-492

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YMYW Podcast Survey: Visit the show notes to access the survey and secret password

Timestamps:

00:00 - Intro

00:37 - Roth Conversion Timing, Order, and 33 Years of Income? (Billy Joe & Bobby Sue, Indiana)

12:32 - Watch Social Security Basics You Need to Know: Common Social Security Questions Answered on YMYW TV, Download the Social Security Handbook

13:17 - I Have $1.2M Capital Gains. Pros and Cons of an Exchange Fund? (Bryan, NY)

23:28 - Download 10 Steps to Improve Investing Success, last chance to complete the 7th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (type in ymyw)

24:15 - We'll Have $7M. Are We Underspending or Overspending in Retirement? (Boston)

35:13 - Should We Keep Life Insurance Policies for Adult Kids with ADHD? (Andrea, Seattle)

41:50 - How Does the 5-Year Rule for Roth Withdrawals Apply to Inherited Roth IRAs? (Karen, TX)

45:15 - Outro

46:22 - The Derails

Alternative Investments, Annuities, and Real Estate Syndications - 491 Aug 20, 2024

What do Joe Anderson, CFP® and Big Al Clopine, CPA think about alternative investments? Andrew in Ohio wants to know. Are real estate syndication deals for real, and a YMYW listener just chose poorly? And Stewart in Serra Mesa is curious whether Joe has changed his position on annuities lately, as rates have "normalized" in the past couple of years? That's today on Your Money, Your Wealth® podcast number 491. Plus, when should Steve in Las Vegas' friend quit her casino job and collect Social Security and child benefits? And how is D in the Midwest's plan for creating income in retirement? Visit the show notes to access the YMYW Podcast Survey and secret password, free financial resources, and episode transcript: https://bit.ly/ymyw-491

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READ THE BLOG: Benefits of Systematic Rebalancing

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YMYW Podcast Survey: Visit the show notes to access the survey and secret password

Timestamps:

00:00 - Intro

00:457 - Real Estate Syndication Deals: Did We Just Make Bad Decisions? (Anonymous)

07:57 - Thoughts on Alternative Investments? (Andrew, OH)

12:54 - Read The Benefits of Systematic Portfolio Rebalancing and Download the Investing Basics Guide

13:31 - Has Joe Modified His Position on Annuities Lately? (Stewart, Serra Mesa, CA)

24:42 - Principal Protected Investing Options for Structured Settlement for a Minor: Annuity? (Speedy Gonzalez, Western NY)

29:52 - 7th Annual YMYW Podcast Survey: your chance at a $100 Amazon e-gift card!

30:35 - When to Stop Work and Claim Social Security and Child Benefits? (Steve, Las Vegas - voice)

34:58 - How's Our Plan for Retirement Income? (D, Midwest)

44:40 - Outro

45:53 - The Derails

Can You Retire? Here's How to Calculate How Much You Need - 490 Aug 13, 2024

Can Claire and her husband retire early at age 60? Today on Your Money, Your Wealth® podcast number 490, Joe Anderson, CFP® and Big Al Clopine, CPA spitball for them and explain how to calculate how much you'll need in retirement. Plus, should Jeff invest his pension money more aggressively, and should he save to his thrift savings plan or his Roth? Should Paula save to her brokerage account or her 401(k)? When and how much should Ken and Fume Guzzler each convert to Roth? The IRS charged Lex late fees for not paying estimated taxes throughout the year on her Roth conversion - find out how to avoid that yourself. Finally, how can Ken get out of an annuity? And is it harmful for Sarah to advise co-workers with little financial experience?

Visit the show notes to access the YMYW Podcast Survey and secret password, all of the following free financial resources, and the episode transcript: https://bit.ly/ymyw-490

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YMYW Podcast Survey: Visit the show notes to access the survey and secret password

Timestamps:

00:00 - 7th Annual YMYW Podcast Survey: your chance at a $100 Amazon e-gift card!

00:46 - Show Intro

01:36 - Retirement Spitball: Do You Agree We Can Both Retire at Age 60? (Claire, OR)

10:03 - Retirement Spitball: More Aggressive With Pension? TSP Instead of Roth? (Jeff, South Carolina)

15:09 - Retirement Spitball: TSP + Rollover IRA = $3M. Convert to Roth? (Fume Guzzler, NYC)

20:33 - Is There a Formula for Retirement? Watch YMYW TV, Download the Retirement Readiness Guide

21:42 - Is It Harmful to Give Advice to Coworkers With Little Financial Experience? (Sarah, Phoenix, AZ)

26:17 - How to Get Out of an Annuity (Ken - voice)

29:03 - Tax-Efficient Retirement Distributions: How's Our Roth Conversion Strategy? (Ken, Southern California - voice)

33:49 - How to Request a Retirement Spitball Analysis

34:40 - IRS is Charging Me Late Fees for Not Paying Estimated Taxes on Roth Conversion! (Lex Martin, Maryland)

38:43 - Should I Save to the Left Pocket (Brokerage) Instead of the Right (401(k)? (Paula, TX)

46:26 - Show Outro

48:02 - The Derails

Good Tax Planning Can Save You HOW Much?! Find Out From IRA Guru Ed Slott, CPA - 489 Aug 06, 2024

The single biggest retirement planning mistake to avoid, the problem with tax professionals, and answers to some of the most frequently asked retirement questions we get on YMYW: should you name a trust as beneficiary on your retirement accounts? What's the break-even point on a Roth conversion? What if you don't have the money to pay the tax when you convert to Roth? Plus, find out the eye-opening amount of money good tax planning can save you! Someone has to be very knowledgeable, entertaining, and special to make it as a guest on YMYW these days, and today on Your Money, Your Wealth® podcast 489, "the IRA guru" Ed Slott, CPA from IRAHelp.com joins Joe Anderson, CFP® and Big Al Clopine, CPA to discuss all of these topics, along with changes to stretch IRAs and required minimum distributions from the SECURE Act and SECURE 2.0 Act. Free financial resources and transcript: https://bit.ly/ymyw-489

50 people will receive a free copy of Ed Slott's new book, The Retirement Savings Time Bomb Ticks Louder, just for having a free financial assessment with Pure Financial Advisors. (10 of those 50 will be randomly selected to receive a copy of the book, signed by Ed Slott!) Schedule your assessment ASAP!

WATCH the video of this interview! https://youtu.be/bgY2ky8XtS0

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Final Regulations for Required Minimum Distributions

Timestamps:

00:00 - Introducing Ed Slott, CPA from IRAHelp.com

01:28 - SECURE Act: Clarity on RMD Rules?

04:31 - How Golf and Football Are Like Retirement

06:25 - The Biggest Retirement Planning Mistake

09:37 - The Value of Ed Slott's Books

14:14 - The Problem With Tax Professionals: Short-Term Tax Planning

17:36 - "I Love Roths Because I Love Tax-Free"

20:50 - What's the Break-Even Point on a Roth Conversion?

21:45 - Can We Trust That Roth IRAs Will Always Be Tax-Free?

24:11 - Your Chance at a $100 Amazon e-Gift Card: Complete the YMYW Podcast Survey

25:04 - SECURE 2.0 Act: Stretch IRA Changes

27:03 - Naming a Trust as Beneficiary of Your Retirement Account: Good Idea?

32:13 - Unnecessary and Excessive Taxes: Why Ed Slott Became the IRA Expert

38:22 - How Much Money Can You Save in Taxes With Good Tax Planning?

43:16 - What About People Who Don't Have the Money to Pay the Tax on a Roth Conversion?

43:50 - Ed Slott's PBS Specials on Retirement

46:28 - How to Get a Free Copy of the Latest Ed Slott Book, The Retirement Savings Time-Bomb Ticks Louder

Market Timing Retirement Withdrawals and Roth Conversions - 488 Jul 30, 2024

Is timing the market when you withdraw money from your retirement accounts or do Roth conversions an effective strategy to minimize tax and maximize returns for YMYW listener Robert? That's today on Your Money, Your Wealth® podcast 488 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, should Doug change his 60/40 asset allocation, and should he start a solo 401(k)? Jefe plans to withdraw from his retirement accounts beyond the top of the 24% tax bracket for the first few years of retirement. Is there any reason to put it in a brokerage account rather than converting it to Roth? The fellas also spitball on Roth conversion methods and strategies for Srinivas, Todd, and Debbie, and JZ in California, and they spitball on JZ in New York's "bucketing" strategy for early retirement withdrawals. Free financial resources and transcript: https://bit.ly/ymyw-488

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Timestamps:

00:00 - Intro

01:42 - Is This the Correct Way to Convert to Roth and Avoid IRS Penalty? (Srinivas, Chicago)

06:51 - Deposit Withdrawals Above Our Tax Bracket in Taxable Account or Do Roth Conversions? (Jefe, TX)

10:12 - Should I Change My Asset Allocation? Should I Start a Solo 401(k)? (Doug, Cave Creek, AZ)

16:22 - Should I Convert $1M IRA to Roth Up to 22% Tax Bracket? (Todd, Flagstaff, AZ)

19:39 - Market Timing Retirement Withdrawals and Roth Conversions (Robert, Southern Maine)

25:28 - My Son Says I Should Do Roth Conversions. Is He Right? (Debbie, Rural Wisconsin)

32:39 - Spitball on Our "Bucketing" Strategy for Early Retirement Withdrawals (JZ, upstate NY)

39:50 - Roll IRA to 401(k) for Backdoor Roth With No Additional Tax? (JZ, California)

43:04 - Hawk Tuah Spitball

45:39 - The Derails

Should Siblings Take Out Life Insurance on Parents Before Inheriting $10M? - 487 Jul 23, 2024

Should Terry and his siblings take out a whole life insurance policy on their parents before they inherit their folks' $10 million worth of farm land? Is Terry on track for retirement? That's today on Your Money, Your Wealth® podcast 487 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, should Fred and Wilma use their 401(k) money for living expenses to bridge the gap until they collect Social Security benefits? Should Glen claim his Social Security at age 65 and use it to fully fund his wife's Roth IRA? When should Bill take his Social Security and should he do Roth conversions? Finally, should Maya include home equity in her retirement savings? Should Jack pay off his mortgage or stash his cash in a brokerage account and refinance his house later? Free financial resources and transcript: https://bit.ly/ymyw-487

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Timestamps:

00:00 - Intro

00:50 - Should I Claim Social Security at 65 to Fully Fund My Wife's Roth IRA? (Glen, Pittsburgh, PA)

04:18 - Should We Use 401(k) to Bridge the Gap Until Social Security? (Fred & Wilma Flintstone, CA)

09:06 - When Should We Take Social Security and Thoughts on Roth Conversions? (Bill, Shippensburg, PA)

15:45 - Should Siblings Take Out Insurance on Parents Before Inheriting $10M? Are We on Track for Retirement? (Terry, IA)

34:14 - Pay Off the Mortgage or Stash Cash in Brokerage and Refinance Later? (Jack, WA)

42:54 - Should I Include Home Equity in Retirement Savings? (Maya, Seattle)

46:02 - The Derails

How to Pay Less Tax and Invest for Retirement - 486 Jul 16, 2024

How is Kimberly's strategy for reducing her retirement taxes by doing Roth conversions and qualified charitable distributions? Is Patrick's tax loss harvesting transaction a wash sale? At what marginal tax rate should Brian stop making Roth 401(k) contributions? Joe Anderson, CFP® and Big Al Clopine, CPA are back this week on Your Money, Your Wealth® podcast 486 to answer these questions and to spitball on the importance of international stock in John in Seattle's diversified investment portfolio, David and Terri's Roth conversion and I bond strategy, Blake's severance package, and the impact of a new home purchase on John in DC's retirement spending. Free financial resources and transcript: https://bit.ly/ymyw-486

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Timestamps:

00:00 - Intro

00:57 - Should We Do Roth Conversions to Top of the 24% Bracket to Minimize $240K I-Bond Profits? (David & Terri, Southern California, voice)

07:32 - Roth Conversion & Qualified Charitable Distribution Strategy Spitball (Kimberly, IA)

13:12 - Should I Take the Severance Package Now at 59 and a Half or Work Until Age 63? (Blake)

18:00 - Is My Tax Loss Harvesting Transaction a Wash Sale? (Patrick, Vancouver, WA)

24:42 - How Important is International Stock in a Diversified Portfolio? (John, Seattle, WA)

30:40 - At What Marginal Tax Rate Should Roth 401(k) Contributions Stop? (Brian, NC)

33:58 - What Impact Will Our New Home Have on Our Retirement Spending? (John in the DC)

42:32 - The Derails

Retirement Planning With a Large Age Difference: A Case Study | YMYW Extra - 6 Jul 09, 2024

He's 56, she's 32. How does this 24-year age difference impact retirement plans for "Bonnie and Clyde", and what strategies should they implement now for the most tax-efficient retirement possible in the future? While Joe Anderson, CFP® and Big Al Clopine, CPA are on vacation, Your Money, Your Wealth® podcast producer Andi Last enlists the help of Pure Financial Advisors' Managing Director Jake Greenberg, CFP®, ChFC® for a video case study (complete with visual aids!) on YMYW Extra number 6. Into which types of accounts should Bonnie and Clyde save for retirement? How much of their savings should they convert to Roth and when? Free financial resources and transcript: https://bit.ly/ymywe-6

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01:19 - Bonnie & Clyde's Financial Situation 06:56 - Health Savings Accounts Explained 08:16 - Real Estate Plans 09:42 - Contribute to Brokerage Account or Roth 401(k)? 11:01 - Bonnie & Clyde's Pre-Financial Assessment: A Video Case Study 23:28 - Tax Diversification Visualized 30:02 - Roth Conversions: When and How Much? Current and Future Tax Brackets Visualized 35:53 - Age Difference and Retirement Date Differences 27:15 - Bonnie and Clyde's Cars, Drinks and Pets 39:57 - Final Thoughts

Spitballing Retirement From Apple to a Tax-Friendly State | YMYW Extra - 5 Jul 02, 2024

Will their $5 million nest egg get them to ages 85 and 100? Pa and GiDi are 65 and 60 and retiring now. As they consider moving to the no-income-tax state of Nevada in retirement, they have some decisions to make: should Pa take Social Security before age 70? How should they bridge the gap until Social Security? And most importantly, how can they minimize their taxes in retirement? Should they wait to do Roth conversions until after the move? That's on this bonus episode of Your Money, Your Wealth®, aka YMYW Extra. While Joe Anderson, CFP® and Big Al Clopine, CPA are on vacation, YMYW producer Andi Last enlists the help of senior financial advisor Kyle Stacey, CFP® from Pure Financial Advisors in San Diego, California. Free financial resources and transcript: https://bit.ly/ymywe-5

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It's a two-fer! Watch the video spitball for Pa and GiDi from Nick Rose, CFP® from the Pure Financial Advisors office in Woodland Hills, California: https://youtu.be/N-hsXonqgMM

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Timestamps: 00:00 - DIY Retirement Guide Limited-Time Special Offer 01:05 - Intro 02:31 - Pa & GiDi's Cars, Drinks & Finances 07:51 - High-Level Thoughts and Retirement Assumptions 11:26 - Roth Conversions to the Top of the 24% Tax Bracket 12:45 - Claiming Social Security and Portfolio Diversification 13:43 - Other Suggestions

Spousal Social Security, Retirement Expenses and Roth Conversions | YMYW Extra - 4 Jun 25, 2024

How much do retirees really spend in retirement? Does the Social Security Primary Insurance Amount (PIA) continue to rise with inflation? Is all the talk about higher future tax brackets just fear-mongering? Can "Johnny Mercer" afford to leave money for his heirs, and what should his strategy be for converting his retirement savings to Roth IRA for tax-free growth on his money? While Joe Anderson, CFP® and Big Al Clopine, CPA each take some much-needed vacation time, Your Money, Your Wealth® producer Andi Last enlists the help of senior financial advisor Rachel Fuss, CFP®, MPH from Joe and Big Al's team of experienced professionals at Pure Financial Advisors in Mercer Island, WA, to see if they can "Ac-cent-tchu-ate the Positive" for Johnny in YMYW Extra number 4. Free financial resources and transcript: https://bit.ly/ymywe-4

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Timestamps:

00:00 - Intro

01:17 - Johnny Mercer's Cars, Drinks and Pets

02:19 - Will Social Security Primary Insurance Amount Continue to Rise With Inflation?

05:20 - Retirement Spending: What's Reality?

06:40 - Are Future Higher Tax Brackets Just Fear-Mongering?

08:21 - How Much Can We Afford to Spend and Still Leave Money for Heirs?

11:07 - Final Considerations & Roth Conversion Strategy

Happily Ever After in Retirement? | YMYW Extra - 3 Jun 18, 2024

Cinderella and her Prince Charming have a nest egg of $2.3 million and are hoping for retirement income of up to $150K/year. When can they afford to retire? How should they coordinate paying for some big purchases, paying off debt, and collecting Social Security benefits as they plan for retirement?

While Joe Anderson, CFP® and Big Al Clopine, CPA each take some much-needed vacation time, YMYW producer Andi Last enlists the help of senior financial advisor Jack Dugan, CFP®, from Joe and Big Al's team of experienced professionals at Pure Financial Advisors in San Diego, to spitball on whether Cindi and her prince can live "happily ever after" on YMYW Extra number 3. Free financial resources and transcript: https://bit.ly/ymywe-3

Watch the video of this spitball! https://youtu.be/zmmCuxEsHiA

Retirement Income Strategies Guide - free download

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Timestamps:

00:00 - Intro

02:28 - Cinderella and Prince Charming's Cars, Drinks & Pets

03:38 - How Much Retirement Income Can They Realistically Expect?

14:05 - How to Pay Off Major Purchases?

15:35 - Other Retirement Savings Strategies

Spitballing Retirement During the Expensive Kid Years - 485 Jun 11, 2024

Market declines just before you retire, or early in your retirement, can really screw up your retirement income strategy. If you're in the middle of the expensive kid years, how do you avoid this sequence of returns risk when making your retirement plans? That's "Jaclyn Smith's" question, today on Your Money, Your Wealth® podcast 485 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, can Vern's wife collect Social Security at age 63, then switch to spousal benefits at age 70? Matt wants to know if 2026 catch-up Roth contributions will be subject to the pro-rata rule, and Tom and Amy are trying to figure out how to avoid Medicare's monthly income-related adjustment amount, or IRMAA, in their plan for Roth conversions. Free financial resources and transcript: https://bit.ly/ymyw-485

How to Build a Recession-Proof Portfolio - YMYW TV

Recession Protection Guide - free download

The Election is Coming: Should You Sell? - read the blog

Investment Vehicle Selection: SMA vs. ETF vs. Mutual Fund – Which One Best Fits You? - read the blog

Is Roth IRA Money Taxed Twice? Watch the latest YMYW Extra

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Ask Joe & Big Al for your Retirement Spitball Analysis

Timestamps:

00:00 - Intro

00:49 - How to Minimize Sequence of Returns Risk When Spitballing Retirement in the Expensive Kid Years? (Jaclyn Smith)

17:18 - Collect Social Security Early at Age 63, Then Switch to Spousal Benefits at Age 70? (Vern, Beautiful Portland Oregon)

23:30 - Will 2026 Catch-Up Contributions to Roth Be Subject to Pro-Rata Rule? (Matt, TX)

23:47 - Should We Do Roth Conversions? What About Medicare IRMAA? (Tom & Amy, Northern MN)

31:51 - The Derails

Roth Conversions vs. Required Minimum Distributions - 484 Jun 04, 2024

Should Mike in Virginia keep using his IRA money to pay the tax on his Roth conversions? How do you do a Roth conversion when you don't have the money to pay the tax? That's PeterLemonJello's question, but is it the question he should be asking? Spitballing Roth IRA conversion strategies to reduce your taxable required minimum distributions (RMD) in retirement - that's today on Your Money, Your Wealth® podcast 484 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Susan and Mike in Ohio are retired, in the 24% tax bracket, and considering converting $50k or $75k to Roth - should they do it? How is D-Rock and Matilda's strategy for selling rental properties and doing Roth conversions as they bridge the gap to early retirement? And finally, how do required minimum distributions work on inherited Roth accounts? Free financial resources and transcript: https://bit.ly/ymyw-484

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Asset Location & Roth Conversion Retirement Spitball - YMYW Extra Ep. 1

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Timestamps:

00:00 - Intro

00:54 - How to Pay the Tax on a Roth Conversion: Are You Asking the Right Question? (Peter LemonJello, FL)

05:45 - Should I Keep Doing Roth Conversions and Paying Tax from the IRA? (Mike, VA)

14:24 - Retired, in the 24% Tax Bracket. Should We Convert $50-$75K to Roth in 2024? (Susan, OH)

18:28 - Roth Conversions and Selling Rental Property to Bridge to Early Retirement (D-Rock & Matilda, New York)

28:11 - Required Minimum Distributions for Inherited Roth IRAs Explained (Elisa, Fremont)

34:12 - The Derails

Asset Location & Roth Conversion Retirement Spitball | YMYW Extra - 1 May 31, 2024

Sunshine in Orange County has been waiting patiently since January for a full Retirement Spitball Analysis: how are her assumptions for rates of return and inflation, her plans for Roth conversions, her asset allocation and asset location, her tax planning, her retirement income and retirement spending plans, and so much more? What missed opportunities is she overlooking?

So many excellent Retirement Spitball requests have come in that Your Money, Your Wealth® hosts, Joe Anderson CFP®, and Big Al Clopine CPA can't handle them all.

On these bonus episodes, called YMYW Extra, producer Andi Last enlists the help of the experienced professionals on Joe and Big Al's team at Pure Financial Advisors. In today's YMYW Extra number 1, thanks to David Cook, CFP® from Pure Financial's San Diego headquarters, Sunshine finally gets her Retirement Spitball Analysis. Free financial resources and transcript: https://bit.ly/ymywe-1

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EASIretirement.com - free retirement calculator

Why Asset Location Matters - download the free guide

More Guides | Blogs | Educational Videos | YMYW Newsletter

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Timestamps:

00:00 - Intro

02:35 - Rate Assumptions

05:58 - Retirement Spending

06:54 - Retirement Income Strategy

12:08 - Retirement Planning: Asset Allocation vs. Asset Location

15:50 - Sequence of Returns Risk

17:53 - Social Security Tax Torpedo

20:01 - Goals & Questions

22:50 - Other Strategies: Qualified Charitable Distributions

24:23 - IRMAA & Tax Optimization

26:37 - Likelihood of Success & DIY Tools

Slopes Vs. Suits: How Couples Bridge the Retirement Gap - 483 May 28, 2024

Are women better investors and financial planners? Today on Your Money, Your Wealth® podcast 483 with Joe Anderson, CFP® and Big Al Clopine, CPA, three different husbands want to retire, while their wives feel they need to work longer. Can Jack and Diane, Mark and Belle, and Mike and his wife hit the slopes now, or do they need to keep wearing their suits? Joe and Big Al spitball on who's right. Plus, should Ellie take her pension in a lump sum or in monthly annuity payments? The fellas also consider a solo 401(k) strategy for self-employed types from our buddy Will. Free financial resources and transcript: https://bit.ly/ymyw-483

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Timestamps:

00:00 - Intro

00:40 - Can We Retire Now or Do We Need to Wait a Few Years? (Jack & Diane, Houston - voice)

09:35 - How to Bridge the Gap in Early Retirement? (Mark & Belle, VA)

19:44 - Help Me Convince My Wife to Retire This Summer! (Michael, MN)

26:28 - Should I Take the Pension Lump Sum or Monthly Annuity Payments? (Ellie, PA)

31:52 - How's My Solo 401(k) Contribution Strategy? (Will)

36:51 - The Derails

FDIC vs. SIPC, Annuities, SSDI & Early Retirement Strategies - 482 May 21, 2024

Will building a new home delay Janelle's early retirement? Can Mike and his wife retire early at ages 50 and 55, and how much should they convert to Roth? Maria and her partner keep their finances separate - can Maria cover her own expenses in early retirement? That's today on Your Money, Your Wealth® podcast 482 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, the fellas explain the difference between FDIC insurance and SIPC insurance for Edward, who wonders if he should spread his assets between banks for protection. Fajita Willy needs a spitball on his MYGA retirement strategy, that is, multi-year guaranteed annuities. Nancy wants to know if mandatory seismic retrofit expenses are tax-deductible. And how should Lee manage Roth contributions and IRMAA now that his Social Security disability has finally been approved and he's received 5 years of back pay? Free financial resources and transcript: https://bit.ly/ymyw-482

Retirement Readiness Guide - free download

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Financial Planning at Every Age: Retirement Planning for Millennials, Gen-X, and Baby Boomers - YMYW TV

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Timestamps:

00:00 - Intro

01:02 - Will Building a New Home Delay My Early Retirement? (Janelle, CO - voice)

07:35 - Should I Spread Assets Between Banks for FDIC Insurance? (Edward, IL)

13:16 - Multi-Year Guaranteed Annuity (MYGA) Retirement Spitball (Fajita Willy, TX)

21:09 - Is the Mandatory Seismic Retrofit Expense Tax-Deductible? (Nancy, Tarzana, CA)

22:47 - My SSDI Was Approved and I've Received 5 Years of Back Pay. How to Manage Roth IRA Contributions and Medicare IRMAA? (Lee, Jacksonville, FL)

28:33 - Can We Retire Early Next Year at Ages 55 and 50? How Much Should We Convert to Roth? (Mike, NY)

34:57 - My Partner and I Maintain Separate Finances. Can I Cover My Own Expenses in Early Retirement? (Maria, Chicago suburbs, IL)

42:06 - The Derails

Which Account Should Fund Living Expenses in Retirement? - 481 May 14, 2024

Should 70-year-old Bob live off of capital gains and dividends from his mutual funds plus Social Security, or should he sell poor-performing mutual funds for living expenses and reinvest the cap gains and dividends? Which account should Neal's 76-year-old Mother use for living expenses? Should Neal and his wife fund their Roth 403(b) until retirement, or contribute to the regular 403(b) and then do Roth conversions after they retire? That's today on Your Money, Your Wealth® podcast 481 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, the fellas spitball on whether IndyGuy can retire at 64 and Die With Zero, and Rod doesn't want a spitball, but he'd like a dart on the wall as to whether his retirement savings will last until age 88. Free financial resources and transcript: https://bit.ly/ymyw-481

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Timestamps:

00:00 - Intro
00:48 - Living Expenses: Cap Gains, Dividends & Social Security or Poor Performers? (Bob, Jupiter, FL)
10:02 - From Which Account Should 76yo Mom Withdraw Living Expenses? (Neal, Dallas, TX)
18:11 - Dart on the Wall for Our Retirement to Age 88? (Rod)
26:08 - Can We Retire at 64 and Die With Zero? (IndyGuy)
35:50 - Save to Roth 403(b) or Traditional Until Roth Conversions at Retirement? (Neal, Dallas, TX)
42:54 - The Derails

401(k) vs. Roth: Where to Save for Retirement - 480 May 07, 2024

Kyle and his fiancée are in their 30s, have done a great job saving, and are in a high tax bracket. Would it make more sense for them to contribute to their 401(k)s or Roth 401(k)s for retirement? Mick's wife Pam has both W-2 and sole proprietor income - where should she save for retirement? That's today on Your Money, Your Wealth® podcast 480 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, the fellas spitball for Janet on where junk bonds belong in a portfolio, they untangle the pro-rata and aggregation rules concerning 401(k) to Roth conversions for Nancy, and they spitball on whether Cary and Mark should retire now or work for two more years when pensions will provide them an extra $50K a year. Free financial resources and transcript: https://bit.ly/ymyw-480

2024 Key Financial Data Guide - free download

Timeless Wisdom from Warren Buffet and Charlie Munger, Berkshire Hathaway's Dynamic Duo - read the blog

Understanding Stock Market Indexes - read the blog

Free retirement calculator - EASIretirement.com

Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Timestamps:

00:00 - Intro
00:57 - We're in Our 30s and in a High Tax Bracket. Where Should We Save for Retirement? (Kyle, WI)
07:34 - Junk Bonds Explained (Janet, the Bronx)
13:19 - Does Pro-Rata Rule Apply When Converting 401(k) to Roth 401(k)? (Nancy, SE Wisconsin)
20:37 - We Have $4M. Should We Retire Now or in Two Years When Pensions Provide an Extra $50K/Year? (Cary & Mark, Los Angeles)
27:50 - How to Save for Retirement with Sole Proprietor and W-2 Work? (Mick, Davis, CA)
36:47 - The Derails

Tax Loss Harvesting, Tax Gain Harvesting, Financial Advisor Value - 479 Apr 30, 2024

Linda is retired and financially independent. Her advisor suggests she have a separately managed account specifically for tax loss harvesting. Today on Your Money, Your Wealth® podcast 479, Joe Anderson, CFP® and Big Al Clopine, CPA spitball on how to save as much tax as possible on retirement withdrawals. Plus, Brian wants to know if it ever makes sense to put IRA money into a brokerage account, rather than doing Roth conversions, so the fellas explain the benefits of tax gain harvesting. Also, why is Robert and Jane's financial advisor constantly trading in Jane's professionally managed account? Pete wants to know if flat-fee financial advisors are worth their fee, and Daniel needs financial guidance for his 34-year-old daughter. He's also considering a free assessment, but he doesn't really know what he's getting himself into, so Joe and Al explain. Free Financial Resources & Transcript: https://bit.ly/ymyw-479

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Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Timestamps:

00:00 - Intro

00:55 - Separately Managed Account for Tax Loss Harvesting To Optimize Retirement Withdrawals? (Linda, MD)

11:54 - Why is Our Advisor Constantly Trading in Our Professionally Managed Account? (Robert, GA)

18:00 - Are Flat-Fee Advisors Worth the Fee? (Pete, Knoxville, TN)

27:03 - Financial Planning for 34-Year-Old Daughter and Pure's Free Assessment (Daniel, Whittier)

35:17 - Does Moving from IRA to Brokerage instead of Roth Ever Make Sense for Tax Gain Harvesting? (Brian, Albany, NY)

42:12 - The Derails

How to Manage Taxes When You Win the Lottery - 478 Apr 23, 2024

So you won the lottery - congratulations! After you celebrate, should you rip off the band-aid and convert the entire lump sum payment to a Roth IRA? That's today on Your Money, Your Wealth® podcast 478 with Joe Anderson, CFP® and Big Al Clopine, CPA. Also, Bucky in WA is required to have the same asset allocation in his traditional and Roth 401(k). Joe and Big Al spitball on his options, along with the pros and cons of consolidating retirement accounts for Scott in NC, and they explain the spousal Roth IRA for Rock Rochester in Manistique, MI. Plus, should Scott in Jackson, MS sign up for the state public employees' retirement system or a traditional retirement plan? Can Driving Fast, Loving Life in TX speed away in her Porsche from RSU capital gains? And should she and her hubbs retire abroad? Finally, can Sean in Reno, NV buy a million dollar vacation home in 10 years, and can Jennifer in La Mirada, CA afford to retire after being forced out of a 21-year career? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-478

Timestamps:

00:00 - Intro
01:06 - Should We Convert $1.75M Lottery Winnings To Roth?
09:31 - Free Financial Assessment - schedule now
10:38 - Asset Allocation Must Be the Same in 401(k) and Roth 401(k). What to Do? (Bucky, Washington state)
18:08 - Pros and Cons of Consolidating Retirement Accounts (Scott, NC)
23:28 - Spousal Roth IRA Explained (Rock Rochester, Manistique, MI)
27:07 - Traditional Retirement or PERS State Retirement? (Scott, Jackson, MS)
31:00 - Avoiding RSU Concentrated Position and Capital Gains and Retiring Abroad (Driving Fast, Loving Life in TX)
38:43 - Restricted Stock Units (RSU) - read the blog
Employee Stock Purchase Plans (ESPP) - read the blog
39:19 - Should We Buy a $1M Vacation Home in 10 Years? We'll Have $12M. (Sean, Reno, NV)
43:11 - Can I Afford to Retire After Being Forced Out of a 21-Year Career? (Jennifer, La Mirada, CA)
49:24 - The Derails

What's the Break-Even Point on Roth Conversions? - 477 Apr 16, 2024

Are there ever times when going all Roth isn't the best strategy? How do you determine the break-even point on doing Roth conversions? That's today on Your Money, Your Wealth® podcast number 477, as Joe Anderson, CFP® and Big Al Clopine, CPA spitball on marginal vs. effective tax rates for Joseph Allen, saving to after-tax brokerage or pre-tax 403(b) for Gigi in Illinois, the arithmetic of Roth conversions for Carl Spackler in Florida, and the mega backdoor Roth for Jefe in Texas. For something completely different, we'll wrap it up with a discussion of tax forms that need to be filed for your solo 401(k) depending on the account balance, for Smitty in The Villages. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-477

Timestamps:

00:44 - Marginal Vs. Effective Tax Rate: Going All Roth Isn't the Best Strategy? (Joseph Allen, Wichita, KS)
14:32 - Free retirement calculator EASIretirement.com
15:37 - I'm 43 and Will Have $2.4M in Retirement. Should I Save to After Tax Brokerage or Pre-Tax 403(b)? (Gigi, IL)
23:17 - Is There a Break-Even Calculation for Roth Conversions? (Carl Spackler, FL)
29:30 - Retirement Income Strategies Guide - free download
How to Create a Steady Stream of Retirement Income - YMYW TV
30:38 - Mega Backdoor Roth: Must I Convert Traditional IRA When I Roll After-Tax Money? (Jefe, TX)
36:29 - Must I File Form 5500-EZ If Solo 401(k) Had No Balance at Year-End? (Smitty, The Villages)
42:18 - The Derails

Which Mortgage for Early Retirement? What is Private Credit? - 476 Apr 09, 2024

What is private credit and where does it fit in your investment portfolio? At age 60, Hope is tired of working and she's hoping to retire in 2-3 years. Should she factor home equity into her retirement spending plan with a reverse mortgage? Which mortgage option for a Houston dream home is best for Nisa in San Jose's early retirement goals? That's today on Your Money, Your Wealth® podcast number 476 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Wayne in Phoenix needs to know how the section 121 tax exclusion works on a vacation home, and Jack and Jill in the UAE have questions about tax gain harvesting and the foreign earned income exclusion. Finally, are Joe and Big Al off their strategy game? A Spotify listener takes the fellas to task about the Affordable Care Act subsidy discussed in episode 472, and challenges their spitball for Duke and Daisy's retirement spending plan in episode 475. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-476

Timestamps:

• 00:00 - Intro • 01:03 - What Is Private Credit? (Janine, La Jolla, CA) • 08:07 - Is a Reverse Mortgage Right for Me? (Hope) • 14:21 - Using Reverse Mortgages To Secure Retirement with Dr. Wade Pfau - YMYW Podcast 117 • How Your Home Can Create Retirement Income - YMYW TV • 14:59 - Which Mortgage Option is Best for Me in Early Retirement? (Nisa, San Jose, CA) • 24:04 - Section 121 Tax Exclusion on a Vacation Home? (Wayne, Phoenix, AZ) • 26:48 - What You Need to Know Before Filing Your Taxes in 2024 webinar • 2024 Tax Planning Guide • 27:39 - Foreign Earned Income Exclusion: Can I Harvest Long-Term Capital Gains? (Jack & Jill, UAE) • 37:06 - ACA Subsidy & Retirement Spitball: Are Joe and Big Al Off Their Strategy Game? (Spotify commenter) • 45:02 - The Derails

Is Your Retirement Withdrawal Rate Too High? - 475 Apr 02, 2024

Will Duke and Daisy's retirement spending plan work? If you're a fan of hearing Joe Anderson, CFP® and Big Al Clopine, CPA debate, you're in luck today on Your Money, Your Wealth® podcast 475, as they disagree on assumptions when it comes to retirement planning. The EASIretirement.com calculator says Chuck in South Carolina could convert even more to Roth, and the fellas spitball on the pros and cons. Plus, what should Chuck's asset allocation be for his daughters, and how should Scott in Kansas City's parents allocate their assets? Can Rothaholic undo his Roth conversion? Brian Fantana and his wife are in their 30s and want to retire at 60. Are they on track? Ricky in Alabama wants to avoid Medicare's IRMAA, or income related monthly adjustment amount. Should he spend from his IRA or from his Roth? Daniel in Whittier wants to know what exactly counts for IRMAA income, anyway? And finally, Elisa in Fremont wants to know, with the new SECURE Act 2.0 rules, when can you transfer 529 college savings funds to Roth? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-475

Timestamps:

00:00 - Intro
01:07 - Will Our Withdrawal Rate Be Too High If We Retire in 3 Years? (Duke and Daisy, Charlotte, NC)
10:50 - Withdrawal Strategy Guide
Retirement calculator
11:28 - EASIretirement.com Says I Should Convert More to Roth. Asset Allocation for Daughters? (Chuck, SC)
22:13 - Can I Undo My Roth Conversion? (Roth Aholic)
27:55 - In Our 30s, Want to Retire at 60. How Are We Doing? (Brian Fantana, WA)
30:36 - What's the Right Asset Allocation for Aging Parents? (Scott, Kansas City, MO)
32:00 - Free financial resources:
32:51 - IRA vs. Roth for Living Expenses? (Ricky, Birmingham, AL)
35:50 - What Counts for Medicare IRMAA? (Daniel, Whittier, CA)
39:49 - SECURE Act 2.0: When Can We Transfer 529 College Savings to Roth? (Elisa, Fremont)
44:44 - The Derails

How to Take the Uncertainty of Taxes Off the Table - 474 Mar 26, 2024

Jimmy in Wisconsin will have a pension, Social Security, and a seven year retirement shortfall. How should he cover it? Skipper in Texas has some unusual pension options, which makes the most sense for his retirement needs? That's today on Your Money, Your Wealth® podcast 474 with Joe Anderson, CFP® and Big Al Clopine, CPA. Should Mike and Carol in Virginia wait to do Roth conversions if they'll be in a lower tax bracket in retirement? Where should Duncan in Texas invest in the 10 years before he retires early? Would it be stupid for Jay Z in Minnesota to miss out on free Roth opportunities? Can Ben in San Francisco's "friend" use the rule of 55 on a rollover retirement plan? And finally, YMYW is fun, but of limited value, according to a recent review. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-474

Timestamps:

00:51 - Pension & Social Security: How Should We Cover Our 7 Year Retirement Shortfall? (Jimmy, WI)
08:17 - 2:1 Matched Company Money vs. My Contribution: What to Do With My Pension? (Skipper, TX)
15:46 - EASIretirement.com free retirement calculator
16:47 - Should We Wait on Conversions If We'll Be in a Lower Bracket in Retirement? (Mike & Carol, Falls Church, VA)
24:22 - Where Should I Invest My Early Retirement Savings for the Next 10 Years? (Duncan, TX)
30:18 - Is It Stupid to Miss Free Roth Opportunities? (Jay Z, MN)
37:46 - Complete Roth Papers Package - free download
38:33 - Rule of 55 on a Rollover Retirement Plan? (Ben, San Francisco)
44:34 - Comment: Fun but limited value (Wemby2024)
50:41 - The Derails

Does Your Financial Advisor Just Want to Collect Fees? - 473 Mar 19, 2024

Why would a financial advisor suggest that Frank in Lake Wobegon sell a piece of inherited property, pay 25% tax, and invest the lump sum? Mark in Florida is 72 and invested in CDs. Should he go back to his financial advisor, or just buy more CDs? That's today on Your Money, Your Wealth® podcast 473 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Adam in Tennessee will have deferred income in 5 years. Should his asset allocation be more conservative? And in order to retire early at age 55, should Lewis in Arkansas delay starting Roth conversions? But first, if Mike's wife outlives him, how can he keep her in a similar tax bracket? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-473

Timestamps:

00:00 - Intro
00:48 - If My Wife Outlives Me, How Do We Keep Her in a Similar Tax Bracket? (Mike)
06:49 - Long Term Capital Gains: Retirement and Real Estate Spitball (Frank, Lake Wobegon)
15:58 - 10 Tax-Cutting Moves to Make Now - YMYW TV
Top 10 Tax Tips - free download (for a limited time only!)
2024 Tax Planning webinar
17:04 - I'm 72. Should I Go Back to an Advisor or Just Buy More CDs? (Mark, FL)
21:32 - Should My Deferred Income Asset Allocation Be More Conservative? (Adam, Franklin, TN)
30:16 - Investing Basics Guide - free download
31:13 - Should We Delay Starting Roth Conversions to Retire Early by Age 55? (Lewis, AR)
41:11 - The Derails

Will Roth Conversions Put You On Track to Retire Early? - 472 Mar 12, 2024

Rob and his wife in North Carolina are 51 and 44 and would like to retire in the next 3-5 years. Are they on track, and what should they consider as far as Roth conversions are concerned once the tax brackets go back up, which they're slated to do when that provision in the Tax Cuts and Jobs Act sunsets at the end of 2025? Is Mark in West Virginia on track to retire at 59 and a half, and do Joe and Big Al have any pointers on how he can find the love of his life? Mike and Gina in Rhode Island are optimistic about retiring early at 61 and 58, but is their optimism delusional? Jake in rural Michigan is self employed. Can he do Roth conversions to retire at age 60 and hang with Big Al in Hawaii? Retirement readiness and Roth conversions, today on Your Money, Your Wealth® podcast 472 with Joe Anderson, CFP® and Big Al Clopine, CPA. But first, the fellas spitball on a retirement and real estate strategy for (50 Shades of) Grey and Elena in Massachusetts. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-472

Timestamps:

01:04 - Real Estate Puts Us in High Bracket. Max Retirement & Roth, Save to Brokerage? (Grey & Elena, MA)
11:57 - Social Security Basics You Need to Know: Common Questions Answered - YMYW TV
Social Security Handbook - free download
12:48 - Roth Conversions After 2025? Are We on Track for Our Retirement Goals in 3-5 Years? (Rob, NC)
19:34 - On Track for Retirement at 59.5? How to Find the Love of My Life? (Mark, West Virginia)
24:24 - Is Our Early Retirement Optimism Delusional? (Mike, RI)
31:16 - EASIretirement.com - free retirement calculator
32:19 - Self-Employed: Roth Conversions to Retire Early and Hang with Big Al in Hawaii at 60? (Jake, rural Michigan)
45:19 - The Derails

How Much Should You Convert to Roth IRA? - 471 Mar 05, 2024

Big Tex, Paul in Maryland, and Nick in Alabama all need to know how much money they should convert to Roth to pay as little tax as possible, today on Your Money, Your Wealth® podcast 471 with Joe Anderson, CFP® and Big Al Clopine, CPA. Johnny and June forgot to convert their backdoor Roth money - are they in trouble? Darren in Nevada has no plans at all to do Roth conversions, but surprisingly still listens to YMYW, and still wants a spitball on his retirement and real estate investment strategies. Plus, can Lolly Pop in New Jersey be less miserly and back off on saving for retirement? Can John in South Carolina use this year's lower income to reduce his Medicare premiums? And finally, if Ordinary Guy in Boston meets an untimely demise, should that change his plans to retire early? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-471

Timestamps:

00:00 - Intro
00:58 - Can I Use This Year's Lower Income to Reduce My Medicare Premiums? (John, South Carolina - voice)
04:39 - Forgot to Convert our Backdoor Roths. Are We in Trouble? (Johnny and June, Oakland, CA - voice)
07:47 - Is Retiring This Year Doable? Should We Convert to Roth? $1.8M Saved, Spend $140K/Year (Big Tex - voice)
13:55 - DIY Retirement Guide - limited time offer - download by Friday, March 8, 2024!
15:05 - Should I Convert My Entire SEP-IRA If I'm Staying in the Highest Tax Bracket? (Paul, Baltimore, MD)
20:51 - $11M+ at Age 46. How Much Roth Conversion and When to Retire? (Nick, AL)
24:42 - Can I Back Off on Retirement Saving So I Can Be Less Miserly? (Lolly Pop, NJ)
30:43 - Financial Markets Master Class webinar - watch on demand
31:24 - Spitball on My Retirement and Real Estate Investment Strategies (Darren, NV)
38:28 - Should My Untimely Demise Change Our Early Retirement Plans? (Ordinary Guy, Boston, MA)
48:10 - The Derails

Spitballing Retirement for Fat Wallets - 470 Feb 27, 2024

Barney and Betty in Maryland hit the jackpot. How's Barney's strategy for net unrealized appreciation, retirement withdrawals, and asset location for his $5 million employee stock ownership plan? Nick in the PNW will have $8 million when he retires early at 53. Should he contribute to his 401(k) or do the good ol' mega backdoor Roth until then? Those are just a couple of the fat wallets Joe Anderson, CFP® and Big Al Clopine, CPA spitball on, today on Your Money, Your Wealth® podcast number 470. Plus, should Allen in New Braunfels' recently widowed sister contribute to her traditional IRA and do some Roth conversions? Should Alicia in Denver take Social Security early to pay off her rental property, and how can Vern in Wickenburg Arizona buy a new home before or during the sale of his current home? Finally, Bryan in Washington needs to know the best investment strategy for his thrift savings plan, and Lyse in Georgia wonders when in a market downturn you should start spending your cash. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-470

Timestamps:

01:06 - Retirement Spitball Analysis for My Widowed Sister (Allen, sunny New Braunfels, TX)
06:52 - $5M ESOP Strategy: Net Unrealized Appreciation, Retirement Withdrawals, and Tax Location (Barney & Betty, MD)
18:07 Why Asset Location Matters - free download
Are You Ready to Retire? Review Your Retirement Readiness - YMYW TV
19:00 - Should I Take Social Security Early to Pay Off My Rental Property? (Alicia, Denver, CO)
23:22 - How to Buy a Home Before or During the Sale of My Existing Home? (Vern, Wickenburg, AZ)
26:50 - Should I Buy a Qualified Longevity Annuity Contract as a Long Term Care Insurance Alternative? (Ron, IL)
31:08 - I'll Have $8M When I Retire at 53. Should I Contribute to 401(k) or Do the Mega Backdoor Roth Until Then? (Nick, PNW)
37:05 - EASIretirement.com - free retirement calculator
38:06 - What's the Best Thrift Savings Plan Investment Strategy? (Bryan, WA)
40:21 - When in a Market Downturn Should You Start Spending Cash? (Lyse, GA)
46:00 - The Derails

401(k) Ins & Outs, Roth Conversion Benefits, and Divorce Finances - 469 Feb 20, 2024

Erik in MN is divorced, and the OC Birdman of South OC is getting divorced. Should Erik contribute to pre-tax retirement accounts or Roth? How should the Birdman and his soon-be-ex time the sale of their house and the filing of their taxes? That's today on Your Money, Your Wealth® podcast 469 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Don has questions about the 401(k) rule of 55 and excess 529 plan college savings. Valerie in Portland wants to know what to do with her old 401(k), and how to invest her new retirement accounts. An advisor tells K-Dog in IN to save cash or open a Roth, then live on those funds and get free ACA "Obamacare" healthcare in early retirement. Is that really possible? Also, what should be Laura in WA's sequence of retirement withdrawals, and is there any benefit to her doing Roth conversions? Should RJ in CA convert his or his wife's rollover IRA to the top of the giant 24% tax bracket? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-469

Timestamps:

00:00 - Intro
01:06 - 401(k) Rule of 55 and Excess 529 Plan Funds (Don, Everywhere, USA)
06:03 - What to Do With Old 401(k) and How to Invest New Retirement Accounts? (Valerie, Portland, OR)
10:33 - 10 Steps to Improve Investing Success - free download
Protecting Your Retirement Income - YMYW TV
11:39 - Is My Early Retirement Spending & Free Healthcare Plan Really Possible? (K-dog, Northern IN)
22:13 - Should I Contribute to Pre-Tax or Roth Post-Divorce? (Erik, Minneapolis)
28:27 - How to Sell House and File Taxes While Finalizing Divorce (OC Birdman in South OC)
32:27 - Q1 2024 Financial Markets Update Webinar, Feb 28, 2024, 12pm Pacific - register now
33:07 - What's the Sequence of Retirement Withdrawals? I Don't See the Benefit of Roth Conversions (Laura, Seattle - Olympic Peninsula)
40:42 - Roth Conversion to the Top of the Giant 24% Bracket? Which Rollover to Convert First? (RJ, Anaheim)
49:09 - The Derails

How Much to Save in Tax-Free, Tax-Deferred, and Taxable Accounts? - 468 Feb 13, 2024

Are there general guidelines on what percentages of your investment portfolio should be in tax-free accounts like your Roth, tax-deferred accounts like your 401(k), and taxable accounts like your brokerage? Joe Anderson, CFP® and Big Al Clopine, CPA spitball on tax diversification today on Your Money, Your Wealth® podcast 468 for Brian in Naperville, IL. William in NH also wants to be tax-diversified. Is his Roth conversion strategy a mistake? Should he be converting much more to Roth? The fellas also do a retirement spitball analysis for Tom in Spokane, WA, and for Claire in CO, who wants to retire next year. Plus, how does Matthew in CT calculate excess Roth contributions, and how should Thomas in IA reallocate assets he over-contributed to his brokerage account? But first a couple of voice messages: Now that Sean in FL no longer has a traditional IRA, can he use the backdoor Roth strategy? We kick things off with a question from Joe in Dallas on how to account for taxes on the money you'll be spending in retirement. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-468

Timestamps:

01:06 - How to Account for Taxes on What I'll Spend in Retirement? (Joe, Dallas, TX (voice)
06:13 - Now That I Don't Have a Traditional IRA, Can I Do a Backdoor Roth? (Sean, FL - voice)
10:29 - 2024 Key Financial Data Guide - free download
11:35 - Spitball Our Financial Status and How to Reach Our Retirement Goals (Tom, Spokane, WA)
17:42 - Tax Diversification General Guidelines? (Brian, Naperville, IL)
23:23 - Goal: Tax Diversification. Is My Roth Conversion Strategy a Mistake? Should I Convert Much More? (William, NH)
29:12 - Retirement Pop Quiz and Free Financial Assessment
30:04 - Spitball If I Can Retire in 2025 (Claire, CO)
34:39 - How to Calculate Excess Roth Contributions? (Matthew, CT
38:23 - Over-contributed to Brokerage. How Should I Reallocate Assets? (Thomas, Iowa)
42:55 - The Derails

What Does Retirement Look Like for You? - 467 Feb 06, 2024

What does retirement at age 60 look like for Allison in Northern Virginia? The EASIretirement.com calculator says Jimmy and Rosalynn in Georgia are on track to reach their retirement goals, even though they're late starters - but are they being realistic? Ingrid used the free EASIretirement.com calculator too, but is she able to contribute more than her annual income to her 403(b) and her Roth? That's today on Your Money, Your Wealth® podcast number 467 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Perry and his wife in Winston-Salem also have 403(b) plans and they wonder if they should take the lifetime annuity or the managed payout in retirement? Finally, should Brad in Sarasota, Florida reserve his health savings account money for long term care insurance? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-467

Timestamps:

00:00 - Intro
00:48 - What Does Retirement at 60 Look Like for Me? (Allison from Northern Virginia)
09:19 - Retirement Rescue Plan - YMYW TV
Retirement Rescue Guide - free download for a limited time only! Get it by this Friday
09:59 - Late Starters. EASIretirement.com Says We're OK. Are We Being Realistic About Retirement? (Jimmy & Rosalynn, GA)
16:07 - Earnings vs. Contributions When Using EASIretirement.com (Ingrid)
21:36 - EASIretirement.com - free retirement calculator
22:37 - Lifetime Annuities or Managed Payouts from Our 403(b)s in Retirement? (Perry, Winston-Salem, NC)
28:54 - Should I Reserve Health Savings Account (HSA) Money for Long Term Care? (Brad, Sarasota, FL)
34:11 - The Derails

Roth Conversions to Pay Less Tax on Retirement Withdrawals - 466 Jan 30, 2024

Should Peter LemonJello, who has high income, and his wife, who is retired with zero income, file their taxes as married filing separately so they can start Roth conversions? What are the tax implications of Roth conversions for Randy in Chi-town, an early retiree in the 32% tax bracket? Caity with a C in SLC is self-employed and over the income max to contribute to a Roth, so now what? And Ben in Oceanside, CA wants to know what impact Roth conversions will have on required minimum distributions after age 73? Joe Anderson, CFP® and Big Al Clopine, CPA spitball on all these Roth conversion tax reduction strategies, today on Your Money, Your Wealth® podcast 466. Plus, does the math make sense on a company-matched Kai-Zen indexed universal life insurance policy for Kickass Seabass in New Jersey? Ed in Virginia wants to know the earnings limits for family Social Security benefits. But first, can JJ in Florida's retirement portfolio handle withdrawals of $150,000 per year? And from the banks of the Mighty Mississippi, what should midwestfabs' post-employment asset allocation be? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-466

Timestamps:

00:00 - Intro
01:12 - Can Our Retirement Portfolio Handle $150K Annual Withdrawals? (JJ, FL)
04:08 - What Should My Asset Allocation Be, Post-Employment? (Midwestfabs)
11:43 - 2024 Financial Market Outlook: read the blog by Brian Perry, CFP®, CFA, Pure Financial Advisors' Executive Vice President and Chief Investment Officer
12:39 - Tax Spitball: Married Filing Separate and Start Roth Conversions? (Peter LemonJello, FL)
14:58 - Roth Conversion Tax Implications for an Early Retiree in the 32% Bracket (Randy, Chicago)
21:34 - Self-Employed and Over the Max to Contribute to Roth – Now What? (Caity, Salt Lake City)
25:07 - Impact of Roth Conversions After Age 73 on RMDs (Ben, Oceanside, CA)
28:12 - Mile Markers to Retirement - YMYW TV
Retirement Readiness Guide - free download
28:52 - Does the Math Make Sense on a Company-Matched Kai-Zen IUL Policy? (Kickass Seabass, NJ)
34:53 - Social Security Family Benefits Earnings Limits (Ed, VA)
42:42 - The Derails

Personal Finance 101: How to Teach Teens About Money - 465 Jan 23, 2024

How and what should we teach teenagers about money, to make the next generation financially literate? That's what CJ in Philadelphia and Teresa want to know, today on Your Money, Your Wealth® podcast 465 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Hap and Bee have a military pension and VA disability - Joe and Big Al spitball on when they'll be able to retire, and what they need to do to get there. And they spitball on whether Grace in Seattle is on track to retire early at age 55. David and Victoria in Grand Rapids, Michigan are killing the game - in their early 30s with $400,000 income and over a million saved. When should they start funding the traditional retirement accounts instead of the Roth accounts? And, find out how the first annual Anderson Household Financial Summit went!

Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-465

Timestamps:

00:00 - Intro
00:53 - Financial Guidance for Teenagers (CJ, Philadelphia - voice)
07:43 - How to Start a Finance 101 High School Course? (Teresa)
13:12 - EASIretirement.com - free retirement calculator
14:18 - Military Spitball: When Will I Be Able to Retire (Hap & Bee, CA)
22:56 - Anderson Family Financial Summit
26:03 - Spitball If I Can Retire Early at Age 55 (Grace, Seattle)
33:02 - 10 Will & Trust Mistakes to Avoid | Estate Planning - YMYW TV
Estate Plan Organizer and Survivor's Guide - free download
33:51 - Killing it at 34, When to Consider Contributing to Traditional IRA? (David & Victoria, Grand Rapids, MI)
44:43 - The Derails

Tax Strategies, Backdoor Roth, Buy vs. Rent - 464 Jan 16, 2024

It's a voice message extravaganza as Joe and Big Al talk about tax gain harvesting on Dante in New York's daughter's custodial account, and the tax impacts of Leon in Chicago investing in his brokerage account. The fellas also spitball on whether Michelle in San Diego, en route to San Francisco, should buy or rent in her 60's, the mega backdoor Roth and the pro rata rule for Sean and his cichlids in Winter Springs, Florida, and whether Jason in NOLA can do the backdoor after recharacterizing his contribution. Plus, should Kevin in Ohio make like the Steve Miller Band and "take the (pension) money and run"? Can Scott in Colorado make like Johnny Paycheck and "take his job and shove it" when it's time for the rule of 55? And should Suzi and Peter consider long term care insurance and protecting their assets with an irrevocable trust?

Access this week's free financial resources and the episode transcript in the podcast show notes at https://bit.ly/ymyw-464

Timestamps:

01:07 - Custodial Account Tax Gain Harvesting: Reported on My Daughter's Taxes or Mine? (Dante, NY - voice)
05:17 - Tax Impacts of Investing in a Brokerage Account? (Leon, Chicago - voice)
10:50 - Three (okay, four) ways you make YMYW the show that it is
Ask Joe & Big Al On Air for your Retirement Spitball Analysis
12:28 - Is it Better to Buy or Rent in My 60s? (Michelle, San Diego - voice)
19:50 - Mega Backdoor Roth & the Pro-Rata Rule (Sean, Winter Springs, FL - voice)
26:56 - Should I Take the (Pension) Money and Run? (Kevin, OH - voice)
32:13 - Money Makeover Guide - limited time special offer - download by this Friday!
Complete Money Makeover - How to Do a Financial Facelift - YMYW TV
33:08 - Should We Consider Long Term Care Insurance and Protecting Our Assets with an Irrevocable Trust? (Suzi & Peter, San Diego)
39:23 - Can I Do a Backdoor Roth After a Re-characterization? (Jason, NOLA)
43:42 - Spitball My Early Retirement Plan & the Rule of 55 (Scott, CO)
52:29 - The Derails

Retirement Investing, Roth Conversion Pros & Cons: YMYW Best of 2023 - 463 Jan 09, 2024

We're revisiting your favorite Your Money, Your Wealth topics and Derails of 2023 in this Roth and retirement investing mega-episode. Safe investing when you're risk averse, mutual funds vs. ETFs, stable value funds, and estimating retirement income needs when you're a young saver with a pension made the YMYW best of 2023 on the investing side. On the Roth side, what to do when there's too much money in your traditional IRA, whether Roth conversions are really as good as they sound, and who's right about the Roth conversion strategy, our listener or his advisor?

Timestamps:

01:05 - How to Safely Invest and Protect $400K When You're Risk Averse (Tyler, OH – voice - from episode 425, among YMYW most popular 2023 episodes on YouTube)
07:43 - Stable Value Fund Vs. Brokerage Account for Living Expenses? (Sharon, Waukesha - voice - from episode 424, among YMYW most popular 2023 episodes on Apple Podcasts)
17:02 - Mutual Funds vs. ETFs in a Tax-Advantaged Account? (Midwestfabs, St Paul, MN from episode 420, among YMYW most popular 2023 episodes on Spotify)
23:40 - How Should Young Savers Invest Pensions and Estimate Retirement Income Needs? (Adam, Oregon - from episode 413, among YMYW most popular 2023 episodes on Spotify)
29:43 - I'm Not Sure Roth Conversions Are as Good as They Sound! (Christine, Seattle - from episode 440, among YMYW most popular 2023 episodes on Apple Podcasts)
39:31 - Who's Right About My Roth Conversion Strategy, Me or My Financial Advisor? (Brad, Sarasota, FL - from episode 409, published at the end of 2022, but one of our 2023 top viewed on YouTube)
49:17 - We Have Too Much in Traditional IRA. How's Our Roth Conversion Plan? (Kelly, Idaho - from episode 423, among YMYW most popular 2023 episodes on YouTube)
01:00:59 - The Best YMYW Derails of 2023

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-463

Emotional Investing - YMYW TV
Emotionless Investing Guide - our special offer for a limited time, download it by this Friday!
Ultimate Guide to Roth IRAs - free download
Episode Transcript & YMYW Best-Of 2023 Lists!
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Can You Retire Early at Age 50 or 60? - 462 Jan 02, 2024

Can Clark Kent's dad in Hutchinson, Kansas retire at age 50? Will Devin in South Carolina be fat and happy or cutting calories if he retires at 59 and a half? Can Scott Magic in Idaho retire to a good and simple life at age 60? Gina and her wife are 52 and 58. Can they retire in four years, and how much should they be putting in their Roth accounts? Plus, Frenchie in Maine needs a spitball on a Roth conversion strategy with Canadian retirement funds, and Andi shares what she knows about target date funds.

Timestamps:

00:49 - Can Superman's Dad Retire at Age 50? (Martha Kent, Hutchinson, KS)
07:23 - Can We Retire to a Good Simple Life at Age 60? (Scott Magic, ID)
14:12 - Fat & Happy in Retirement or Cutting Calories at Age 59 and a Half? (Devin, SC)
20:56 - We're 52 and 58. Can We Retire in 4 Years? How Much Should We Put in Roth? (Gina, WA)
28:06 - Canadian Retirement Roth Conversion Strategy? Target Date Funds? (Frenchie, Maine)
37:06 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-462

EASIretirement.com free retirement calculator
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Roth & Retirement Spitball, Insurance, and the Origins of YMYW - 461 Dec 26, 2023

Spitballing on early retirement and Roth conversions to finish 2023. How can Jack and Diane (no, the other, other Jack and Diane, these are the ones in Rochester, MN) bridge the gap to retirement at age 61? Can Michael in San Diego do a Roth conversion without it impacting his taxes? Plus, what should "the Flintstones" do with their whole life insurance policies? What spitballs of wisdom do the fellas have for Michael, who is "benefit-less" in Kansas City, MO? Then, we wrap up the final episode of the year with the YMYW origin story.

Timestamps:

00:48 - How to Bridge the Gap to Retirement at Age 61? (Jack & Diane, Rochester, MN)
06:04 - Can I Convert to Roth Without Impacting My Taxes? (Michael, San Diego)
10:22 - What to Do with Whole Life Insurance Policies? (Wilma & Fred Flintstone)
16:55 - Financial Strategies for the "Benefitless" (Michael, Kansas City, MO)
23:46 - The Origins of YMYW
36:14 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-461

The Complete Roth Papers Package
Financial New Year's Resolutions: Tips for Getting Your Finances in Order
The Economy, Currencies, Stocks, and 2024: End of Year Market Update webinar
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

How to Invest: Bonds, CDs, and Roth Conversions - 460 Dec 19, 2023

Joe and Big Al spitball on investing in index funds, bonds, CDs, treasuries, annuities, net unrealized appreciation on company stock, and where to park cash right now. Plus, how do taxes, Roth conversions or the Mega Backdoor Roth, and donor advised funds factor into those investing strategies? Will and Debbie in Gettysburg are investing an inheritance, LJ in Philly and Jane want the fellas' take on the pros and cons of various safe investments, Roger and Jessica in Cowtown Ft. Worth need four different financial spitballs, and should M.E. in Atlanta do a Roth conversion and put money in a donor-advised fund in the same year? But first, Dianna in Spotsylvania needs an investing plan for her 86-year-old Mom.

Timestamps:

00:57 - Investment Spitball for 86yo Mom: Index Funds? Roth IRA and Conversions? (Dianna from Spotsylvania, Virginia)
05:57 - How Should I Invest My Inheritance? (Will and Debbie, Gettysburg, PA)
14:12 - How's My Laddered CD Investing Strategy? (LJ, Philly)
17:07 - Tax on Treasuries vs. CDs vs. Annuity: Where to Park Cash Right Now? (Jane)
22:27 - NUA Company Stock, De-Risking With Bonds, & Mega Backdoor Roth (Roger & Jessica, Ft. Worth)
34:13 - Donor Advised Fund and Roth Conversion in the Same Year? (M.E., Atlanta)
40:54 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-460

Top 10 Tax Tips Guide (limited time offer - download by this Friday!)
10 Tax-Cutting Moves to Make Now - YMYW TV
Investing Basics Guide
10 Steps to Improve Investing Success
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Advisor Touts 8% Returns, But Says I Can Only Withdraw 4%?! - 459 Dec 12, 2023

Do financial advisors have some secret blood handshake that they'll all claim they can get you 8 percent returns, but then tell their clients they can only withdraw 4 percent in retirement? That's Mark in Minnesota's question today on YMYW. Plus, should Matthew in Seattle quit the DIY approach to his finances and hire a fee-based financial planner? What do Joe and Big Al think about Steven in Connecticut's "opposite of sequence of returns risk" strategy for retirement withdrawals and "bonuses"? Can listener Joe have an active and comfortable retirement at age 62? Elle in Los Angeles needs some spitballing on contributing to traditional or Roth 401k, student loans, and the potential tax benefits for paying mother in law for babysitting. The fellas also answer some more last-minute year-end tax questions for George, and for Chuck in Idaho. But first, Mike in CO gets priority with his voice message about tax loss harvesting.

Timestamps:

01:08 - Any Reason Not to Do Tax Loss Harvesting? (Mike, Steamboat Springs, Colorado - voice)
05:46 - Should I Switch from DIY to a Fee-Based Financial Planner? (Matthew, Seattle, WA)
16:00 - If Advisor Touts 8% Returns, Why Can I Only Withdraw 4%? (Mark, MN)
24:49 - 3% Retirement Withdrawals + Bonuses = Opposite of Sequence of Returns Risk? (Steven, CT)
31:05 - Can I Have an Active and Comfortable Retirement at Age 62? (Joe)
36:35 - 401k Vs Roth 401k Contributions, Student Loans, and Babysitting Tax Benefit (Elle, Los Angeles)
41:16 - When to Pay Taxes on a 2023 Roth Conversion? (George)
43:26 - Cost Basis: First In First Out to Minimize Taxes? (Chuck, ID)
47:27 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-459

EASI Retirement Spitball Analysis: YMYW TV
EASIretirement.com Free Retirement Calculator
6 Secrets to Bigger Tax Savings from Your Nonprofit Donations: YMYW TV
Tax-Smart Charitable Giving Guide
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Retirement Spending and Timing Your Mortgage Payoff - 458 Dec 05, 2023

Should Brian in Binghamton, New York pay off his mortgage for a guaranteed 6% return? How bad did Steve in Pittsburgh screw up his retirement, and can he afford to buy a new house away from his a-hole neighbors? Can Susan and her husband in Cape Canaveral Florida retire in a year and a half and should they pay off their mortgage? And how can Edith and Archie in Kansas maximize Roth Conversions and factor paying off the mortgage into their retirement spending strategy? Plus, Steve and Marcia in Indiana and Florida wonder about their retirement spending and whether they should collect Social Security now or wait until age 70, and should Sunny D in Arizona keep potential withdrawals in cash or sell investments as needed to satisfy required minimum distributions (RMDs)? We kick things off with Shelly's voicemail about investing the proceeds from the sale of a business.

Timestamps:

00:58 - How to Invest $1M From the Sale of a Business? (Shelly - voice)
06:55 - RMDs: Keep Potential Withdrawals in Cash or Sell Investments as Needed? (Sunny D, AZ)
10:00 - Pay Off Mortgage for Guaranteed 6% Return? (Brian, Binghamton, NY)
15:52 - How Bad Did I Screw Up My Retirement? Can I Afford to Buy a New House? (Steve, Pittsburgh)
21:40 - Can We Retire in 1.5 Years? Should We Pay Off the Mortgage (Susan, Cape Canaveral, FL)
32:14 - How to Maximize Roth Conversions While Spending From Our Portfolio and Paying Off the Mortgage (Archie & Edith, KS)
39:39 - Retirement Spending and Collecting Social Security Now or Wait to Age 70? (Steve & Marcia, Indiana & Florida)
47:56 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-458

Withdrawal Strategies Guide
Free Financial Assessment
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

How to Cut Your Taxes Before Year-End - 457 Nov 28, 2023

Last-minute tax questions answered: should Brad in Wahoo, NE save to his regular 401(k) instead of his Roth 401(k) so he can claim the American Opportunity Tax Credit? Should Jennifer and Zeke in NY set up a Roth IRA and file taxes for their 13-year-old that's got some earned income? Does Cindy in San Diego have to report her Medicare Advantage over-the-counter medication benefit on her taxes? And should our buddy Carl Spackler wait until the new year to deposit his rollover check? Plus, Em in FL needs ideas for moving her Mom from a low-cost-of-living area to a high-cost-of-living area, Wannabe Landlord wonders about creating an LLC for his real estate, and can CJ in FL and IN report pro-rated real estate expenses on schedule E? Finally, the 5-year rule on Roth withdrawals once again, this time for Brutus Buckeye, and Bruce from Joisey is back, this time he wants to pay cash for a car.

Timestamps:

01:08 - American Opportunity Tax Credit and Other Tax Strategies (Brad, Wahoo, NE)
05:07 - Tax Filing for 13-Year-Old With Earned Income (Jennifer & Zeke, NY state)
09:47 - HSA: The Last Month Rule for Health Savings Accounts (JZ, New York)
13:01 - Income Tax and Sales Tax Explained (Cindy, San Diego - North County)
16:23 - Deposit Rollover Check After New Year to Avoid the Pro-Rata Rule? (Carl Spackler, FL)
21:12 - Strategies for Mom to Move from LCOL to HCOL Area (Em, FL)
26:28 - LLC For Real Estate Investment Properties? (Wannabe Landlord)
28:28 - How to Report Pro-Rated Real Estate Expenses on Taxes (CJ, Florida & Indiana)
32:22 - 5-Year Roth IRA Withdrawal Rule - Sigh (Brutus Buckeye, Columbus, OH)
37:41 - Should I Pay Cash for a Car? (Bruce, Joisey)
43:15 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-457

Reduce Your 2023 Taxes With These End-of-Year Tax Planning Strategies (free on-demand webinar)
End-of-Year Tax Strategies Guide
DIY Retirement Guide (LIMITED TIME OFFER! Download by Friday, Dec. 1, 2023!)
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

How to Bridge the Gap to Retirement Income: Pension Spitball - 456 Nov 21, 2023

Planning to retire early? Joe and Big Al spitball on bridging the gap to your retirement income when there's a pension in the mix, today on Your Money, Your Wealth® podcast 456. Manley and his wife are in their early 50s and have teacher's pensions. Can they retire in 2 and a half, or even one and a half years? Can Bucky in the Midwest retire in 2024, and can Henry Karl Kittensburg III retire in about 3 years, with all the milk his heart desires? How should Paul in Houston choose his pension options for early retirement? Is Greg in Southern California's CalSTRS teacher's pension enough for his retirement? Keaton Money in Colorado needs the fellas to help him decide between his pension's fringe benefits and brokerage account returns, and big Paw in a mid-Atlantic state asks for a spitball on how to reduce taxes on an impending headcount reduction lump sum payout.

Timestamps:

00:58 - Early 50s, Teacher's Pensions. Can We Retire Early in 1.5 or 2.5 Years? (Manley, Nashville)
08:17 - How to Choose Pension Options for Early Retirement (Paul, Houston, TX)
18:25 - Is CalSTRS Teacher's Pension Enough in Retirement? (Greg, Southern California)
22:02 - Am I In Good Shape to Retire in 2024? (Bucky from the Midwest)
23:32 - Pension Fringe Benefits vs. Brokerage Account Returns (Keaton Money, CO)
32:00 - Can We Retire at Age 59? (Henry Karl Kittensburg III, Western OH)
40:42 - How to Reduce Taxes On a Headcount Reduction Retirement Lump Sum Payout? (Big Paw, mid-Atlantic state)
50:50 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-456

Retirement Income Strategies Guide
EASIretirement.com free retirement calculator
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Can High Earners Fund a Roth IRA Without Paying More Tax? - 455 Nov 14, 2023

Steve & Sharon in Minnesota are high earners - can they get more money into their Roth IRA without paying more tax? Should Fred in western New York do Roth conversions before required minimum distributions kick in? If Mike in Utah saves on healthcare premiums now, will that mean large RMDs and tax bills for him later? Should Mark in Maryland do a backdoor Roth after maxing out his 401(k)? And should Joseph in Kansas contribute to his new employer's traditional or Roth 401(k)?

Timestamps:

00:49 - Should We Do Roth Conversions Before RMDs Kick In? (Fred, western NY)
10:22 - Will Saving on Healthcare Premiums Now Mean Large RMDs and Tax Bills Later? (Mike, UT)
19:36 - Where to Invest After Maxing Out 401(k)? Backdoor Roth? (Mark, MD)
28:04 - How to Get More into Roth Without Paying More Tax? (Steve & Sharon, Roseville, MN)
39:24 - Roth 401(k) or Traditional 401(k) With New Employer? (Joseph from Wichita, KS)
47:08 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-455

End-of-Year Tax Planning Webinar - live and free, tomorrow Nov 15, 2023, 12pm Pacific, 3pm Eastern - register now!
How to Build a Recession-Proof Portfolio - YMYW TV
Recession Protection Guide - free download
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Is Our Retirement Savings Enough to Ever Retire? - 454 Nov 07, 2023

Will Ron and Candy in Connecticut ever be able to retire, and are Bruce and Selina in Philly saving enough to retire? That's today on Your Money, Your Wealth® podcast 454 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, are Pebbles and Bam Bam in Kentuckystone missing anything when it comes to using their brokerage account to pay Roth Conversion taxes? And Susan in San Diego is 55, spends about $36K a year, and has almost a million saved - can she retire yet? And finally, our buddy Will knows he shouldn't time the market, but….

Timestamps:

00:50 - Will We Ever Be Able to Retire? (Ron, CT)
09:54 - Are We Saving Enough to Retire? (Bruce and Selina, Philadelphia)
17:36 - What Am I Missing? Brokerage Account Spitball (Pebbles & Bam Bam, Kentuckystone)
27:05 - Nearly $1M at 55, Spending $36k/Year: Can I Retire Early? (Susan, San Diego)
31:36 - I Know We Shouldn't Time the Market, But… (Will)
40:46 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-454

How to Cruise Into Your Retirement - YMYW TV
Cruising Into Retirement Checklist - download by this Friday!
EASIretirement.com free retirement calculator
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

No Retirement Advice or Recommendations, Just Spitballing - 453 Oct 31, 2023

Can Jessie and Becky in Iowa retire now at age 52? Should Robert and his wife file their taxes separately, to pay less tax on their required minimum distributions? Can Joe and Al validate Mike in Minnesota's retirement plan, and does a backdoor Roth make sense for him? How in the world will Mike in New York be able to retire at a reasonable age? And what will retirement income look like for Marty in San Diego? Just spitballs here, no retirement advice!

Timestamps:

00:49 - Can We Retire Now at Age 52? (Jessie and Becky, IA)
10:09 - Should We File Taxes Separately to Minimize Taxes on RMDs? (Robert)
19:56 - Validate Our Retirement Plan: Does a Backdoor Roth Make Sense? (Mike, MN)
25:11 - How in the World Am I Going to Retire at a Reasonable Age? (Mike, Utica, NY)
29:19 - What Will Our Retirement Income Look Like? (Marty, San Diego)
35:06 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-453

Retirement Readiness Guide - free download
Retirement Pop Quiz - how well do you know retirement?
EASIRetirement.com - free retirement calculator
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Why Would a Tax Advisor Discourage 529 Plan College Savings? - 452 Oct 24, 2023

Why does Becca in Florida's advisor "poo-poo" her strategy for funding 529 plans for education? Keith, commenting on Spotify, wants to know about reimbursing yourself from a 529 plan for the scholarship amount used for education without penalty, and Wendy way up in New York wants to know if she should use retirement funds to pay for college and home renovations. Plus, what are the pros and cons of starting Roth conversions for Renee in Wisconsin, and is she on track for retirement? Will the IRS penalize Dan in Michigan for not paying Roth conversion tax in January? With the 5-year Roth clock, how does compounding interest work when Aaron in Ohio changes custodians? And Kirk in Iowa wonders how the Affordable Care Act tax credit works with dependents.

Timestamps:

00:55 - Why Doesn't My Financial Advisor Want Me to Fund 529 Plans? (Becca, FL)
08:19 - Is 529 Plan Self-Reimbursement for Scholarships Okay? (Keith)
10:22 - Should We Use Retirement Funds to Pay for College and Home Renovations? (Wendy, way up in north NY)
18:11 - Pros and Cons of Starting Roth Conversions: Are We On Track for Retirement? (Renee, WI)
28:58 - Is the IRS Going to Penalize Me For Not Paying Roth Conversion Tax in January? (Dan, Milford, MI)
30:38 - Roth 5-Year Clock: Compounding Interest on Rolled Over Retirement Accounts (Aaron, OH)
32:19 - How Does the Affordable Care Act Tax Credit Work with Dependents? (Kirk, IA)
37:11 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-452

ABCs of College Funding - free download
Money Saving Tips fro Funding College - YMYW TV
How to Save for Education; 529 Plan, Coverdell, Prepaid Tuition and More - on-demand webinar
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Mega Backdoor Roth Conversion 5-Year Rule and Bond Investing - 451 Oct 17, 2023

Should Jim in New Jersey do the YMYW-infamous Megatron (the Mega Backdoor Roth IRA) or use his Roth 401(k) - and how can he keep bonds out of his Roth accounts? Joe and Big Al discuss the January first start date when it comes to the 5-year rule on Roth conversions for Nancy in Wisconsin, and they spitball on those Roth clocks for withdrawals and tax-efficient investments for Johnny Mercer in Savannah, GA, who also wants to know the pros and cons of bonds vs. bond funds vs. CDs. Plus, should Brad in St. Louis incorporate bonds into his investment portfolio, given the fact that he will have pensions and Social Security providing 5 streams of fixed income in retirement?

Timestamps:

00:58 - The Megatron: Mega Backdoor Roth IRA vs. Roth 401(k) (Jim, NJ)
14:42 - 5-Year Rule on Roth Conversions: How Does January First Default Start Date Apply? (Nancy, WI)
19:43 - 5-Year Rule on Roth Conversions vs. Tax-Efficient Investments, Bond Funds Vs. Bonds Vs. CDs (Johnny Mercer, Savannah, GA)
32:42 - What's the Best Strategy for Incorporating Bonds into Our Retirement Portfolio? (Brad, St. Louis)
40:09 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-451

Complete Roth Papers Package - includes the Roth Basics Guide, the 5-Year Rules for Roth IRA Withdrawals, and the Ultimate Guide to Roth IRAs
10 Steps to Improve Investing Success
Investing Basics Guide
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Retirement Withdrawals: What's a Safe Distribution Rate? - 450 Oct 10, 2023

How much can you safely spend in retirement? Is the four percent rule outdated? Joe and Big Al spitball on a safe retirement distribution rate for those in the 55-60 age range for Clay in Ohio. They also spitball on withdrawal rates when there's a pension in the mix for Jonny and June in the Bay Area of California, and for William in Maryland, who is concerned he might be exposing himself to sequence of returns risk by spending too much in early retirement. Plus, when does Dan have to take required minimum distributions from the IRA he inherited from his Dad in 2021? Finally, Wayne in San Diego wants to know how to protect his bank accounts from FedNow, the Federal Reserve's new peer-to-peer payment system.

Timestamps:

00:53 - What's a Safe Retirement Distribution Rate? (Clay, OH)
07:57 - Can We Retire at Ages 50 and 48? (Johnny & June, East Bay, CA)
19:01 - Spitball My Retirement Withdrawal Rate (William, MD)
24:50 - When Am I Required to Take Money From My Inherited IRA? (Dan)
28:54 - How to Protect Money From FedNow? (Wayne, San Diego)
32:37 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-450

Withdrawal Strategy Guide - free download
Withdrawal Trap Doors: How to Avoid Them! YMYW TV
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

What To Do With Your Employer-Sponsored Retirement Plan? - 449 Oct 03, 2023

What should Martin do about his outrageously fee-heavy 403(b) plan? Should EF hedge his pre-tax non-qualified 415 excess plan? What should Max do with his old TIAA plan, and what are the pros and cons of a cash balance defined benefit plan for self-employed people like Brent Money? Plus, Mike needs Joe and Big Al's spitball on the highly compensated employee rule and excess 401(k) contributions, and the fellas explain how employee stock purchase plans are taxed for Big Cheese Bob the Tomato.

Timestamps:

00:55 - What to Do About My Outrageous Fee-Heavy 403(b)? (Martin, Miami, FL)
05:56 - Should I Hedge My Pre-Tax Non-Qualified 415 Excess Plan? (EF, Kansas)
14:25 - What to Do With My Old TIAA Retirement Plan? (Max, Seattle)
24:29 - Highly Compensated Employee Rule and Excess 401(k) Contributions (Mike, Castleton, NY)
29:16 - How Are Employee Stock Purchase Plans (ESPP) Taxed? (Big Cheese/Bob the Tomato)
32:26 - Cash Balance Plans Pros and Cons for Self-Employed (Brent Money, Bennington, NE)
40:52 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-449

Investing Basics Guide - free download
Financial Boot Camp: Investing Basics - new from YMYW TV
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Low Mortgage Interest Rate vs. Future Gains: Is Trading Up Worth It? - 448 Sep 26, 2023

Coach Dobber and his wife in Edina, Minnesota have a low mortgage interest rate and a decent amount of home equity. Should they put that equity to work and take the risk on buying a higher value home at a reduced price, even if it means a much higher interest rate and higher monthly payments too? Plus, Joe and Big Al spitball for Adam, in the birthplace of aviation, on the taxation of passive rental income, and capital gains from his portfolio and the sale of his business, prior to his early retirement. They also spitball for Charles in Idaho, on taxes on the sale of his mother-in-law's house. And should Dan's wife and business co-owner retire from the business and take Social Security Disability? And will Social Security be reduced for everyone? Steve in Vegas has a cautionary tale to tell.

Timestamps:

00:55 - Stay With a Low Mortgage Rate, or Buy Up at a Reduced Price? (Coach Dobber, Edina, MN)
16:10 - Early Retirement Taxes on Rental Income and Capital Gains? (Adam, Dayton, OH)
24:55 - How to Figure Taxes on Sale of Mom's House (Charles, ID)
29:47 - Should Spouse and Business Co-Owner with Alzheimer's Retire and Take Social Security Disability? (Dan, Midwest USA)
36:04 - Will Social Security Be Reduced for Everyone? A Cautionary Tale (Steve, Las Vegas)
44:17 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-448

2023 Key Financial Data Guide
EASIRetirement.com - new free retirement calculator!
Social Security Handbook
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Can You Shorten Your Working Years? - 447 Sep 19, 2023

Can Sven and Olga in Minnesota shorten their working years? Should PJ in Michigan take his pension lump sum or the annuity payments, and should he maintain an aggressive asset allocation in retirement? Plus, the fellas spitball early retirement strategies for Joe in Massachusetts and Nick in California, and they discuss how to tell the difference between post-tax contributions and pre-tax funds converted to Roth at tax time for Victor.

Timestamps:

00:45 - Can We Shorten Our Working Years? (Sven & Olga, MN)
07:50 - Pension Lump Sum or Annuity? Aggressive Asset Allocation in Retirement? (PJ, Michigan)
23:31 - Can We Retire at Ages 55 and 52? (Joe, MA)
29:54 - Help Me Spitball Some Retirement Goals (Nick, CA)
35:07 - Post-Tax Contributions and Pre-Tax Funds Converted: How to Tell the Difference? (Victor)
39:40 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-447

Retirement Income Strategies Guide
Register for the Investing 101 webinar, Wednesday, Sept 27, 12pm PT
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

DIY Early Retirement Planning - 446 Sep 12, 2023

Should Jackson and Elsa from Wyoming fire their financial advisors and shop for lower fees, or switch to do-it-yourself financial planning? Can 34-year-old Bob in Texas retire early at 50, and what's the best way for him to put an extra $30K to work? How much should 35-year-old Matthew in the middle of nowhere Wisconsin be saving for retirement in pre-tax accounts vs. post-tax accounts? And finally, should Michelle in Minnesota leave excess education savings in a 529 plan or move it to a Roth IRA?

Timestamps:

00:58 - Should We Fire Our Advisors and Go DIY or Shop for Lower Fees? (Jackson & Elsa, WY)
11:51 - Can We Retire at Age 50? Best Way to Put Extra $30K to Work? (Bob, TX)
19:51 - How Much Should We Save for Retirement Pre-Tax vs. Post-Tax? (Matthew, Middle of Nowhere, WI)
28:27 - Excess 529 Plan College Savings: Leave it or Move it to Roth? (Michelle, MN)
35:34 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-446

DIY Retirement Guide - limited time offer, download by Friday 9/15/23!
EASIRetirement.com - free retirement calculator
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Market Timing, Pension, & Roth Conversion Retirement Spitball - 445 Sep 05, 2023

How will a diet COLA on a pension affect retirement plans for Joe and Barb in Tulsa? Percy in South Carolina has a pension too. He's timing the market, but should he change his investing strategy as he approaches retirement? Plus, Michael in Virginia needs ideas to fund a custodial Roth IRA for his 3-year-old and 2-month-old kids, and Rocco in NYC catches Big Al on capital gains exclusions. But first, will scary future events mean Michelle in San Diego will have to pay more tax and the highest possible Medicare premiums?

Timestamps:

00:44 - Will Scary Future Events Mean Paying More Tax and Highest Medicare Premiums? (Michelle, San Diego)
10:46 - Market Timing, Pension & Roth Retirement Spitball (Percy, North Myrtle Beach, SC)
18:34 - FERS & Military Pension Diet COLA Retirement Spitball (Joe and Barb, Tulsa, OK)
26:49 - Can I Employ My 3-Year-Old and 2-Month-Old Kids to Fund a Custodial Roth IRA? (Michael, VA)
29:38 - Capital Gains Exclusion: Both Members of a Married Couple Need to Be on Title? (Rocco, NYC)
35:16 - COMMENT: Semi-Retired at 65 (Jetta Jay from Raleigh)
39:00 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-445

EASIRetirement.com - new free retirement calculator!
Retirement Rescue Plan - Your Money, Your Wealth TV
Retirement Rescue Guide - limited-time offer, download by Friday 9/8/23
Episode Transcript
Ask Joe & Big Al On Air

What Are the Rules for Taking Money From a Roth IRA? - 444 Aug 29, 2023

Charles has had it with Joe and Big Al stumbling through the Roth 5-year rules, so he explains to Joe and Big Al, once and for all, the rules for withdrawing money from a Roth IRA. Plus, is Shane missing any retirement risks before he retires early at age 55? Nick wants to know if employers are required to adopt all of the provisions in the SECURE Act 2.0, or if they can pick and choose which to implement, like they can with the rule of 55? Plus, how can Stew offset huge capital gains on the sale of an inherited house, and we revisit whether George can move investments in-kind from an inherited trust to a brokerage account.

Timestamps:

01:57 - Roth IRA 5-Year Rules for Withdrawals Explained (Charles)
10:39 - Any Retirement Risks I'm Missing Before I Retire at Age 55? (Shane, Chester County, PA)
16:42 - Do Employers Have to Adopt All of SECURE 2.0? (Nick, OH)
21:10 - How to Offset Huge Capital Gains Taxes on the Sale of an Inherited House? (Stew, Clairemont)
25:49 - Can I Move Investments In-Kind From Inherited Trust to Brokerage Account? (George, KS - from ep. 433)
34:02 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-444

EASIRetirement.com - new free retirement calculator!
5-Year Rules for Roth IRA Withdrawals Guide - free download
SECURE Act 2.0 Guide - free download
6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card!
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Spitballing Retirement and Social Security for Worst Case Scenarios - 443 Aug 22, 2023

Harsh realities of life can very quickly change your retirement plans and your entire financial future. In this episode, Joe and Big Al spitball on dealing with these realities. What financial strategies can they suggest for William and his 33-year-old wife, who has metastatic breast cancer? Debbie and Emily each experienced the unexpected sudden passing of their partners. Is it possible to minimize the capital gains tax on Debbie's son's inheritance, and can Emily retire in a year? Josie has lousy longevity in her family and wants to plan for the worst case scenario of dying before her husband. Alfred is 81 and concerned that he's going to run out of money before he runs out of time, and Richard has a sobering story that changed his thoughts about when to collect Social Security. Finally, Irene is subject to the Government Pension Offset (GPO) - can she withdraw the money she paid into Social Security?

Timestamps:

01:03 - Financial Strategies for the Young and Disabled (William, TX)
08:16 - How to Minimize Son's Capital Gains Tax on Inheritance (Debbie, HI)
14:37 - Can I Quit Work in a Year? Should I Do Roth Conversions? (Emily, Rochester, MN)
20:22 - Worst Case Scenario Retirement Spitball Analysis (Josie, Atlanta)
28:45 - Are We Going to Run Out of Money? How Much Can We Safely Withdraw? (Alfred Pennyworth)
32:35 - Life Lesson on When to Take Social Security (Richard)
40:15 - Can I Withdraw the $17,000 I Paid into Social Security? (Irene, Bremerton, WA)
46:00 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-443:

Estate Planning Organizer - free download
Social Security Handbook - free download
6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card!
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

RSU, Mutual Funds, Bonds, and Annuities - 442 Aug 15, 2023

What's the best strategy for E-Dog's restricted stock units with his employer, how are RSUs taxed, and how do Roth conversions fit into the mix? Plus, should Jay in Raleigh liquidate his annuities or follow "Stan the Annuity Man's" advice and take the annual payments? Elisa wants to know how a mutual fund portfolio would work in retirement, and what's a good way for listener Joe to invest in bonds in a taxable account to bring his portfolio back into proper balance? Finally, the fellas spitball on Medicare savings vs. Roth conversions for David, and an unrealized gain strategy on an UTMA education savings account for Jay in California.

Timestamps:

00:50 - Restricted Stock Units: RSU Spitball Analysis (E-Dog, Boulder, CO)
14:44 - Annuity Retirement Spitball Analysis (Jay, Raleigh, NC)
26:36 - How Would a Mutual Fund Portfolio Work in Retirement? (Elisa)
31:13 - Asset Location: How to Invest in Bonds in a Taxable Account to Rebalance? (Joe)
35:09 - Medicare Savings Vs. Roth Conversions (David, Logan, NM)
40:04 - UTMA College Savings Unrealized Gain Strategy (Jay, CA)
47:05 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-442

Why Asset Location Matters - free guide
6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card!
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Early Retirement Withdrawals & Capital Gains Tax Explained - 441 Aug 08, 2023

Does the math work for Chris' early retirement plan? What's a safe retirement withdrawal rate for Luke, who wants to be part of the financial independence / retire early or FIRE movement - and what does Joe have against FIRE? Plus, Jake is about to change jobs, can Joe and Big Al uncover any tax planning opportunities for him? The fellas also explain capital gains tax for our buddy Carl Spackler, and they spitball on those capital gains when it comes to selling a house for Olga and for LJ, and Jim wonders about the impact of selling a house on Affordable Care Act subsidies.

Timestamps:

00:54 - Early Retirement Spitball: Does the Math Work? (Chris, Philadelphia)
04:27 - FIRE Withdrawal Rate for Long-Term Capital Preservation? (Luke, Ft. Collins, CO)
14:26 - We're 38 and 33. Any Tax Planning Opportunities Before I Change Jobs? (Jake, VA)
20:48 - Capital Gains Tax Explained (Carl Spackler, FL)
23:55 - House Sale Tax Strategy (Olga, Chula Vista)
26:32 - Do I Need to Worry About Investment Property Sale Proceeds? (LJ, Philadelphia)
30:46 - How Will Selling a Home Impact ACA Subsidies? (Jim, Santa Cruz)
35:52 - New One Star and Five Star Reviews
38:10 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-441

Guide to Cracking the Financial Code at Any Age
FIRE interviews on YMYW
Spitballing Retirement Planning in Your 30s (YMYW podcast 391)
6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card!
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Are Roth Conversions Really As Good as They Sound? - 440 Aug 01, 2023

Christine isn't sure that Roth conversions are all they're cracked up to be. Erick needs a retirement spitball analysis for his Roth conversions, annuities, and the real estate in his self-directed IRA, Billy the disgruntled attorney wants to know if he can retire now, and Zach wonders just how bad is it to rely on the lottery for retirement? But first, Joe and Big Al spitball military retirement strategies.

Timestamps:

01:16 - I'm 22, Military. Should I Be Spending More Instead of Saving So Much? (Cole - voice)
06:19 - I'm 27. How Should I Max Out Military and Second Job Retirement Contributions? (Adam)
09:08 - Retiring With Pensions at Ages 59 & 63. Is Our Retirement Plan Sound? (Scott, AL)
16:55 - I'm Not Sure Roth Conversions Are as Good as They Sound! (Christine, Seattle)
26:44 - Roth Conversion, Annuities, Real Estate in Self-Directed IRA Strategy? (Erick, CA)
37:23 - Can a Disgruntled Attorney Quit and Retire Now? (Billy, Joplin, MO)
39:53 - Just How Bad an Idea Is Relying on the Lottery for Retirement? (Zach, Tuscaloosa, AL)
47:18 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-440:

6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card!
Financial benefits for military families
2023 Key Financial Data Guide
Episode Transcript
Ask Joe & Big Al On Air

$7M Tax-Free or $10M Retirement? Backdoor Roth or Lower Fees? - 439 Jul 25, 2023

Should Carl Spackler stick with his backdoor Roth strategy, or go for lower fees? Should Kevin go all Roth, or stick with his current three tax-diversified buckets strategy? (That depends - would he rather have $7 million tax-free, or $10 million in tax-deferred retirement accounts?) Can Lily claim all the extra allowances she can, to jam as much money as possible into her Roth? Can Dave retire now and ride his motorcycle into the Bavarian Alpine sunset, and does Peggy Lee need to be feverish about the tax underpayment penalty with her Roth strategy?

Timestamps:

00:53 - Do I Need to Worry About a Tax Underpayment Penalty with My Roth Strategy? (Peggy Lee, North Dakota)
07:17 - What Am I Doing Wrong? Can I Retire Now? What About Taxes? (Dave, Germany)
15:28 - Back Door Roth vs. Lower Fees: Which Would You Choose? (Carl Spackler, FL)
21:40 - Should We Go All Roth or Three Tax-Diversified Buckets? (Kevin, NJ )
28:53 - Can I Claim Extra Allowances to Contribute More to Roth IRA? (Lily, San Diego)
33:46 - Should I Split Money Between Multiple Brokerage Firms to Avoid Hacking? (Wesley from Unincorporated Gwinnett County, GA)
40:18 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-439

Register for the Q3 Financial Market Outlook live webinar, July 26, 2023, 12pm PT / 3pm ET
The Ultimate Guide to Roth IRAs
YMYW in US News and World Report's Best Personal Finance Podcasts to Listen to in 2023
Episode Transcript
Big Al's Island Studio (photo)
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

When Will You Be Able to Retire? - 438 Jul 18, 2023

Steven has got "one more year" syndrome. Can he retire at age 65? Today on Your Money, Your Wealth® podcast 438, Joe and Big Al spitball retirement for him, and for MB - can she and her husband live comfortably if she retires at age 59½? And for Johnny - does he have enough to fill the gap until retirement, and should his dad do Roth conversions before Johnny inherits his wealth? Is Austin maximizing his future gains by saving to his 401(k) at age 29, rather than his Roth IRA? But first, how can Mike and his wife leave their kids a lower tax bill when they pass?

Timestamps:

00:45 - How to Leave the Kids a Lower Tax Bill When We Pass? (Mike, Boerne, TX - voice)
04:24 - I Have "One More Year" Syndrome. Can I Retire at 65? (Steven, Exton, PA)
08:30 - Can We Live Comfortably If I Retire at 59½? (MB, Louisville, KY)
12:49 - Do I Have Enough to Fill the Gap Until Retirement? Should Dad Convert My Inheritance to Roth? (Johnny, El Dorado, CA)
21:49 - Am I Maximizing Future Gains By Saving to Pre-Tax 401(k)? (Austin, Naples, FL)
29:42 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-438

Retirement Lifestyles Guide
Register for the Q3 Financial Markets Outlook live webinar, July 26, 2023, 12pm PT / 3pm ET
Episode Transcript
Ask Joe & Big Al On Air

Two Unspoken Assumptions About Collecting Social Security - 437 Jul 11, 2023

YMYW listener Alan feels that there are two unspoken assumptions that many different podcasters make when it comes to claiming Social Security benefits. Joe and Big Al spitball on those assumptions, along with safe retirement withdrawal rates before and after Social Security and pension for Rick and Jen, and a thrift savings plan (TSP) and Social Security retirement strategy for Theresa. Plus, Mark and his wife are semi-retired at 51 and 44. Are they going to run out of money? Where should Mary be saving for retirement, and how should she handle large Roth conversions before required minimum distributions (RMDs) kick in?

Timestamps:

00:45 - Unspoken Assumptions About Collecting Social Security? (Alan, Daufuskie Island, SC)
09:38 - Safe Withdrawal Rates Before and After Social Security & Pension (Rick & Jen, Atwater, OH)
19:25 - Thrift Savings Plan and Social Security Retirement Strategy ("Theresa")
29:28 - Retirement Spitball: Will We Run Out of Money? (Mark, St. George, UT)
37:37 - Where to Save for Retirement and Roth Conversions Prior to RMDs? (Mary, small town Indiana)
47:54 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-437

Social Security Handbook
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Invest or Pay Off the Mortgage? - 436 Jul 04, 2023

It's a common question: should you pay off your mortgage when you have extra cash, or invest for retirement? Joe and Big Al spitball on how Ms. Moneybags and her wife-to-be should use their upcoming windfall. Plus, what should Bob's asset allocation be as he nears retirement? Should Harley and Harlene do Roth conversions after tax rates increase, and should they take advantage of net unrealized appreciation (NUA) on Harlene's company stock? Pete needs a 13 year retirement plan sanity check, Lauren wants to know if she can retire early or at least go part time, and Michael and Carol want the fellas to spitball whether they're on track for retirement.

Timestamps:

00:57 - Should We Pay Off the Mortgage or Invest Our Windfall On the Way? (Ms. Money Bags)
09:00 - What Should My Asset Allocation Be When Nearing Retirement? (Bob in New York)
17:21 - Should We Convert to Roth After Tax Rates Go Up? Should We Leverage NUA? (Harley)
29:04 - 10-13 Year Retirement Plan Spitball Sanity Check (Pete, AL)
38:15 - Can I Retire Early or Go Part Time and Stop Contributing to 401(k)? (Lauren, IL)
43:17 - Retirement Spitball: Are We On Track? (Michael & Carol, Las Vegas)
48:24 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw_436

Portfolio Tracker: How to Manage Your Assets at Any Age
Episode Transcript
Ask Joe & Big Al On Air

How to Maximize Your Inheritance: IRA Options and RMDs - 435 Jun 27, 2023

A little ditty about Jack and Diane, who will eventually inherit about $4.5M from Diane's parents. How do they manage the required minimum distributions? Which of three options should Matt take with his inherited IRA? Making the most of your inheritance today on YMYW 435. Plus, Clay wants to know if it's a good idea to take money off the table and rebalance to safer or more aggressive investments, depending on your risk tolerance? Can Elizabeth offset pre-tax IRA losses with the gains from the sale of rental real estate? Is it true that you can make one time contributions from your IRA to your HSA that is, your health savings account? And finally, can Cory gift stock to his daughters and avoid paying the kiddie tax as a way to pay for college? And can Rich supercharge a 529 college savings plan with himself as beneficiary?

Timestamps:

00:58 - How Do We Manage RMDs on a Pending Inheritance? (Jack & Diane)
11:31 - Which of 3 Options Should I Take With This Inherited IRA? (Matt, San Diego)
18:57 - Should I Take Money Off the Table and Rebalance to Safety? (Clay, Westerville (Columbus), OH)
23:50 - Can I Offset Pre-Tax IRA Losses With Gains from the Sale of Rental Real Estate? (Elizabeth, Lake Forest)
26:43 - Is It True We Can Make One Time Contributions From IRA to HSA? (Scott, NC)
32:06 - How to Pay for College: Gifting Stock and Avoiding the Kiddie Tax? (Cory, Bethesda, MD)
36:16 - Should I Supercharge a 529 Plan With Myself as Beneficiary? (Rich, NY)
41:17 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-435

Estate Planning Organizer
Emotional Investing - YMYW TV
Emotionless Investing Guide
Episode Transcript
Ask Joe & Big Al On Air

Ready to Retire? 5 Retirement Spitball Analyses - 434 Jun 20, 2023

Joe and Big Al spitball five different retirement plans: is Jaybird on track to retire with a decent nest egg? Should Ted and his wife use the retirement smile spending pattern and spend more early in retirement? Is it safe for Aaron to retire at age 59 and a half? How much can Karla convert to Roth for the most tax-efficient retirement withdrawal plan? LEO Jay has Roth TSP retirement strategy questions, and Lynn suggests a super-easy Roth conversion calculator - but Big Al's got an even easier idea.

Timestamps:

00:44 - Are We On Track to Retire With a Decent Nest Egg? (Jaybird, Penciltucky - PA)
08:57 - Retirement "Smile": Should We Spend More Early in Retirement? (Ted)
16:57 - Is it Safe to Retire at Age 59 and a Half? (Aaron, suburb of Philadelphia)
25:42 - Spitball My Tax-Efficient Withdrawal Plan: How Much Roth Conversion? ("Karla", New York City)
34:21 - Should I Max Roth TSP and Retire at 50? When Can I Withdraw from Roth TSP? (Jay, San Diego)
37:00 - Super Easy Roth IRA Conversion Calculator (Lynn)
42:51 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-434

Retirement Pop Quiz: test your retirement knowledge
Retirement Readiness Guide
Episode Transcript
Ask Joe & Big Al On Air - get your own Retirement Spitball Analysis

Bonus Depreciation, Retirement Income, and Portfolio Diversification with Real Estate - 433 Jun 13, 2023

How does bonus accelerated depreciation work when it comes to commercial real estate? Is real estate a good source of retirement income, and can it take the place of safe assets like bonds in your investment portfolio? Plus, can investments be transferred in-kind from an inherited trust to a brokerage account? And what tips do the fellas have for ace-ing the CFP exam and launching a career as a financial advisor?

Timestamps:

00:43 - Bonus Accelerated Depreciation on Commercial Real Estate Purchase (Papa Joe, Naples, FL)
07:04 - Is Real Estate a Good Investment for Retirement Income? (Doctor Jerry, Waco, TX - from episode 426)
13:00 - Is Real Estate a Substitute for Bonds in a Diversified Investment Portfolio? (Don, VA - from episode 416)
17:08 - Can I Move Investments In-Kind From Inherited Trust to Brokerage Account? (George, KS)
24:15 - Tips for Taking the CFP Exam and Building a Career as a Financial Advisor (Craig, St. Clairsville, OH)

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-433

Real Estate Retirement Income Webinar - Wednesday June 21, 2023, 12pm PT/3pm ET - register now
10 Tips for Real Estate Investors Guide
Episode Transcript
Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Tax Jailbreak Early Retirement Strategy: Sense or Nonsense? - 432 Jun 06, 2023

Can you retire early - before age 55 - simply by contributing to your 401(k) only up to the company match and then saving to a brokerage account? Joe and Big Al spitball on using this so-called tax "jailbreak" strategy to retire early. Plus, is Christine on track to have $150,000 present value to live on in retirement? Is John stuck just watching his money grow and turn into big required minimum distributions (RMDs)? Can Jackie contribute to a SEP IRA and convert it all to Roth? And what do the fellas think of Lee's I-Bond emergency fund?

Timestamps:

00:49 - Is the Tax "Jailbreak" Early Retirement Strategy Nonsense? (William)
04:31 - Retirement Spitball: Can I Spend $150K Present Value in Retirement? (Christine, Seattle)
13:18 - Am I Stuck Watching My Money Grow and Being Saddled With Big RMDs? (John, TX - voice)
18:10 - Can I Contribute to SEP IRA and Convert it All to Roth, or Roll it to 401(k)? (Jackie, Bethesda, MD)
23:19 - How is My I-Bond Emergency Fund Strategy? (Lee, Jacksonville, FL)
28:12 - The Derails: One of YMYW's Most Brutal One-Star Reviews Ever

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-432

How to Build a Recession-Proof Portfolio - The latest episode of YMYW TV
Recession Protection Guide
SECURE Act 2.0 webinar (on demand) and companion guide
Episode Transcript
Ask Joe & Big Al On Air

How to Calculate Your Retirement Needs in Future Dollars - 431 May 30, 2023

How much will money will you need in retirement, adjusted for inflation? Joe and Big Al spitball on your future dollars, how to calculate the tax on Roth conversions, and the benefits of converting to Roth when financial markets are down. Plus, should retirement savings contributions be half pre-tax and half post-tax? And finally, saving to a 529 plan for your kids, or sending them to Hollywood stunt training camp - which would you do!?

Timestamps:

00:49 - How Much Will I Need to Retire in Future (Inflated) Dollars? (Jared, Clifton Park, NY)
05:51 - Can We Retire Early With $400K Savings and $80K Pensions? That Depends on the Inflation Factor (Marcus, Queens, NYC - from episode 373)
15:22 - How to Calculate Tax on Roth Conversions & the Benefits of Converting in Down Markets (Robin)
20:00 - Should I Save Half Pre-Tax and Half-Post Tax for Retirement? (John Brown, NV)
28:26 - Hollywood Stunt Training Camp vs. Saving to 529 Plan (Mike, Utica, NY)
33:40 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-431

Big Al's Quick Retirement Calculation Guide
10 Steps to Improve Investing Success
Episode Transcript
Ask Joe & Big Al On Air

How to Consider Your Pension Options for Retirement - 430 May 23, 2023

When should you take your pension, what types of things should you think about when it comes to deciding between a lump sum or a monthly annuity payment - risk protection, for example - and how do you work your pension into your overall retirement plan? Spitballing on retirement pension options, and saving to a taxable account when you're concerned about required minimum distributions or RMDs, on today's show.

Timestamps:

00:42 - When to Collect My Pensions: Now, Early Retirement, or Age 70? (Rose, CA)
12:16 - I'm Concerned About RMDs. Should I Save to a Taxable Account for Retirement? (John Doe, Seattle, WA)
17:33 - Pension Retirement Spitball: Are We On Track to Retire in 2032 Without Saving Any More? (Jennifer & Zeke, NY State)
25:32 - Roth 457 vs. Roth IRA and Pension Options Retirement Spitball (Clay, Westerville, OH - from episode 377)
35:39 - COMMENT: Pension Vs. Lump Sum Risk Protection (Stephen)
38:53 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-430

Key Financial Data Guide
Surviving Retirement Without a Pension - YMYW TV S4E17
Register for a free webinar: Navigating Retirement Solo, tomorrow, Wed. May 24, 2023, 12pm PT/3pm ET
Episode Transcript
Ask Joe & Big Al On Air

HSA to Roth, RMD Investing, and Social Security Strategies - 429 May 16, 2023

Can you convert your health savings account (HSA) to Roth, and do the five-year Roth withdrawal clocks apply? What should you do with money you'd been putting to your student loan debt if you're part of the student loan forgiveness program? What's the best way to invest your RMDs, or required minimum distributions? How does IRMAA, the income-related monthly adjustment amount for Medicare, apply to zero-coupon municipal bonds? And finally, strategies for collecting survivor Social Security benefits.

Timestamps:

00:49 - Can I Convert a Health Savings Account HSA to Roth IRA and Do the 5-Year Rules Apply? (Philip)
07:49 - My Student Loans Were Forgiven. Now Should We Contribute to Roth 403(b)? (Pete, Winston-Salem, NC)
15:37 - How Should I Invest Required Minimum Distributions? (Judy, San Diego)
22:17 - How is IRMAA for Medicare Applied to Zero Coupon Municipal Bonds? (Jimmy)
26:40 - 62 and Widowed: Claim Survivor Social Security Benefits Until Age 67? (Mark, Burke, VA)
30:11 - Is Signing Up for Social Security Just Pretty Much Straight Forward? (Michael)
32:09 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-429

Debt Ceiling and the US Dollar - new educational video
Talking About Recessions - new blog post
Medicare Check-Up Guide
Episode Transcript
Ask Joe & Big Al On Air

What to Do With Inheritance Money? - 428 May 09, 2023

So you're about to receive a large inheritance - what should you do with it? Joe and Big Al spitball on suddenly becoming $85 million dollars richer. Plus, is it nuts to semi-retire early? Should retirement contributions be split between Roth and traditional accounts? Can you do conversions to your kids' custodial Roth accounts? The fellas also spitball tax bracket-based Roth conversion strategies to help you pay the least amount of tax possible, long term, and they discuss required minimum distributions on inherited assets, and whether to pay off a 401(k) loan if it's "paying" you 8% per year.

Timestamps:

00:48 - I'm Inheriting Millions of Dollars. What Should I Do With It? (Michael, Binghamton, NY)
07:04 - Should I Split Retirement Contributions Between Roth and Traditional 457? (Kevin, Folsom, CA - voice)
11:34 - Should I Do 100% Roth TSP Contributions? Am I Nuts to Semi-Retire Early? (Derek, Seattle)
16:30 - Should We Do Roth Conversions to the Top of the 22% or 24% Tax Bracket? (Bill, Maryland)
23:53 - Is My CPA Correct That I Can Convert $24K to Roth Tax-Free? (Sam, Newark, NJ)
26:52 - Can I Convert 457 Money to My Kids' Custodial Roth Accounts? (Brian, Binghamton, NY)
32:50 - RMD Rules for Inherited Roth IRA and Traditional IRA (Dan, Brick, NJ)
38:48 - Should I Pay Off My 401(k) Loan That's "Paying" Me Over 8% Per Year? (Anon, Denver, CO)
42:59 - Comments on Keeping Employer IRA Money Separated
44:46 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-428

Complete Roth Papers Package
Episode Transcript
Ask Joe & Big Al On Air

Trust Issues, Death & Taxes: Estate Plan Spitball - 427 May 02, 2023

If you knew exactly when you were gonna die, so many financial decisions would be simple. But generally, we don't, so today Joe and Big Al spitball on death, taxes, and trust issues of the estate planning variety. Fair warning, it's "the dark show" today on YMYW, as the fellas discuss cancer trust funds, making your trust the beneficiary on your retirement accounts, when and how to take Social Security benefits and pension options, Roth conversion strategies taking into account the 5-year rules for withdrawals, and potentially donating required minimum distributions to charity rather than doing conversions.

Timestamps:

00:49 - Pension Plan Options Retirement Spitball: Lump Sum, Annuity, or Hybrid? (Dave, CO)
07:37 - Should We Have a Cancer Trust Fund? (Melinda, Milwaukee)
12:02 - Why Not Make Our Trust the Beneficiary on Retirement Accounts? (Ms. Merry, MD)
21:40 - Is There a 5-Year Rule on Taking Dividends from a Roth IRA After Age 59½? (Douglas, Bonita, CA)
23:34 - I'm 60, My Ex is 74. Am I Eligible for Spousal Social Security Benefits? (Salwa)
24:39 - How Much If Any Roth Conversion Should We Do? (Paul, NJ/SC)
28:53 - Why Do a Roth Conversion Instead of Donating to Charity? (Kevin, Raleigh)
32:57 - Why Separate and Never Add Money to a Profit-Sharing Plan Rolled to IRA? (Nancy, Foxboro, MA)
35:46 - Retirement Pension at 57 or 60? Social Security at 62 or 70? (midwestfabs)
45:56 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-427

Estate Planning Organizer
Inflation, Interest Rates, Recession? Financial Markets Update Webinar Replay
Going Solo: Navigating Your Financial Future Single - YMYW TV & companion guide
Episode Transcript
Ask Joe & Big Al On Air

Spitballing Retirement Real Estate and Tax Strategies - 426 Apr 25, 2023

Gidget wants to find her very own Moon Doggie so she can get married and reap that sweet, sweet capital gain exclusion when she sells her house. What do Joe and Big Al think, and can they help her find a man? Plus, is real estate a good investment for retirement income? Is taking out a TSP (thrift savings plan) loan to pay off your mortgage a good idea? Also, the fellas spitball a tax and ACA (Affordable Care Act) strategy, a FIRE strategy - well, financial independence, but not necessarily retire early - and they discuss capital gains taxes on RSUs (restricted stock units.)

Timestamps:

00:45 - How's My Marriage Strategy for Extra Capital Gain Exclusion on the Sale of My Primary Residence? (Gidget, San Diego)
10:46 - Is Real Estate a Good Investment for Retirement Income? (Doctor Jerry, Waco, TX)
16:14 - Should I Pay Off My Mortgage with a Thrift Savings Plan Loan? (Jake - voice message)
19:35 - Spitball Our Retirement, Tax Planning, and ACA Strategy? (John from LA - Lower Anderson, SC)
26:31 - Do I Need to Pay Quarterly Capital Gains Taxes When I Sell RSUs? (Jerry, Redmond, WA)
31:43 - FIRE Retirement Spitball Analysis: How to Structure Our Investments? (Jim, Washington State)

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-426

10 Tips for Real Estate Investors
Alternative Retirement Income Sources: Real Estate and Beyond webinar
Real Estate Investing: What Are Cash-on-Cash and Cap Rate? YMYW podcast episode 365
Episode Transcript
Ask Joe & Big Al On Air

Annuity? CD? Money Market? Where to Invest for Safety - 425 Apr 18, 2023

How do you protect your nest egg when you're really risk-averse and want safe, low-risk investments - should you invest in annuities, CDs? When choosing a money market fund, should you just invest in the one with the highest post-tax return? How do you go about replenishing cash, or rebalancing your portfolio, when the stock market is up? Plus, the widow's penalty in relation to Roth conversions, and switching from survivor Social Security benefits to your own. Also - withdrawing from your portfolio before RMD age? One listener says nobody should ever need to do it!

Timestamps:

00:51 - How to Safely Invest and Protect $400K When You're Risk Averse (Tyler, OH - voice)
07:31 - Rebalancing: How to "Replenish Cash" When Stocks Are Up? (Elisa, Fremont, CA)
13:27 - Money Market Funds: Don't I Want the Highest Post-Tax Return? (Michael, CO)
18:42 - The Widow's Penalty and Roth IRA Conversions (KBH, San Antonio)
27:46 - Can I Switch from Survivor Social Security Benefits to My Own at Age 70? (Sara, Tucson, AZ)
30:43 - COMMENT: Come On People, You've Had a Lifetime to Set Up Your Retirement (April, Tinley Park, IL)
36:46 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-425

Withdrawal Trap Doors - YMYW TV episode and free companion guide
Register for the Q1 2023 Market Update / Q2 2023 Financial Market Outlook Webinar, April 26, 12pm PT / 3pm ET with Pure Financial Advisors' EVP and Chief Investment Officer, Brian Perry, CFP®, CFA.
Episode Transcript
Ask Joe & Big Al On Air

Investments vs. Retirement Withdrawal Strategy, FDIC Insurance - 424 Apr 11, 2023

Should retirement living expenses be drawn from your stable value fund, your CD or money market, brokerage account, or FDIC insured bank accounts? Can you even trust the banks after the recent bank failures? What about sequence of returns risk? Which investments are best for long-term retirement savings when you're early in your career? Joe and Big Al explain why your strategy for retirement savings and withdrawals should be your first step - before you consider investments, asset classes, or sectors.

Timestamps:

00:49 - Stable Value Fund Vs. Brokerage Account for Living Expenses? (Sharon, Waukesha - voice)
09:08 - Sequence of Returns Risk: Should I Save for 5 Years in CD, Money Market or Brokerage Account? (Carlos, Tampa Bay)
15:46 - High Income and Tax-Deferred Savings, Low Tax Rate: Where Should I Save? (Josh, Boston, MA)
21:40 - Am I Overcomplicating My Investments at Age 35? (Mike, VA)
29:44 - I'm 28. Should I Max Out Pre-Tax or Post-Tax 457 Plan Retirement Savings? (Michael)
33:55 - How Does FDIC Insurance Work? SVB and Signature Bank Failures (Jon, Powhatan, VA)
39:46 - Should We Roll 401(k) to Several FDIC-Insured IRA Accounts to Live Off Of? (Joan, Long Island, NY)

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-424:

YMYW Guide to Growing Your Wealth
Register for the Q1 2023 Market Update / Q2 2023 Financial Market Outlook Webinar, April 26, 12pm PT / 3pm ET with Pure Financial Advisors' EVP and Chief Investment Officer, Brian Perry, CFP®, CFA.
Episode Transcript
Ask Joe & Big Al On Air

What to Do When There's Too Much Money in Your Traditional IRA - 423 Apr 04, 2023

How can you reduce taxes, IRMAA, net investment income tax, and required minimum distributions when you've got too much money in your tax-deferred retirement account - and just how much Roth conversion should you do? Plus, can you contribute to a Roth by transferring stocks "in kind"? If the check you send off to pay your estimated taxes isn't cashed before the deadline is it late? How does SECURE 2.0 impact 529 plans, and is 529 better than Roth IRA for college savings? Finally, the fellas spitball a 401(k) in-plan Roth conversion and retirement account consolidation strategy.

Timestamps:

00:48 - We Have Too Much in Traditional IRA. How's Our Roth Conversion Plan? (Kelly, Idaho)
10:54 - Can I Make a Roth IRA Contribution by Transferring Stocks "In Kind"? (GDO, Delco)
14:36 - How to Pay Estimated Taxes: If My Check Isn't Cashed Immediately, Is It Late? (Judi, San Diego)
16:51 - 529 Plan vs. Roth IRA: Does SECURE 2.0 Affect 529 College Savings? (George)
20:49 - 401(k) In-Plan Roth Conversion and Retirement Account Consolidation (Steve, Maine)
27:07 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-423:

Tax Takedown: brand new YMYW TV and companion guide
2023 Tax Planning Guide
Episode Transcript
Ask Joe & Big Al On Air

How to Reduce Taxes and Get Better Investing Returns? Asset Location - 422 Mar 28, 2023

Which investments should go in your traditional IRA vs your Roth IRA, and does that asset location depend on your age? Learn how to generate "tax alpha" to get better returns on your investments. Plus, Joe and Big Al spitball whether to roll a TIAA 403(b) to an IRA or take the annuity, and they spitball retirement and Roth conversion and Roth contribution strategies for an overseas officer with a military pension, and for Americans working abroad who qualify for the foreign earned income exclusion.

Timestamps:

00:51 - Best Assets to Hold in Traditional IRA and Roth IRA? (Michael, Colorado - voice)
7:40 - Is Investment Asset Location Dependent on Age? (Glen)
11:35 - TIAA 403(b): Take the Annuity or Roll to an IRA? (Brad, Northeast TN)
19:34 - Military Pension Spitball: Overseas Officer with Fluctuating Income & Taxes (US Grant, Alexandria, VA... usually)
24:29 - Foreign Earned Income Exclusion & Roth 401(k) Rules (Jeff, Singapore via North Dakota)
31:32 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-422:

Why Asset Location Matters Guide
Register for our free 2023 tax planning webinar, March 29, 12pm PT/3pm ET
Schedule a free financial assessment
Episode Transcript
Ask Joe & Big Al On Air

Roth Conversions & Retirement Spitball Analysis - 421 Mar 21, 2023

Should Edith and Archie live off their non-qualified accounts and pay Roth conversion taxes from their 401(k)? How can Johnny from Knoxville do Roth Conversions and stay in a low tax bracket Plus, at age 31, are Shad and his wife saving enough for retirement? What should Tech Chick do with her severance package after being laid off from her tech industry job? Finally, listener comments on retirement plan education, Roth conversions, and the 5-year Roth clocks.

Timestamps:

00:39 - Live Off Non-Qualified Accounts, Pay Roth Conversion Tax From 401(k)? (Edith & Archie, TX)
11:35 - How to Do Roth Conversions and Stay in a Low Tax Bracket + Estimating Taxes (John, Knoxville, TN)
19:11 - Retirement Spitball Analysis: Are We Saving Enough at Age 31? (Shad, Smith's Grove, KY)
27:11 - Laid Off From the Tech Industry. What Should I Do With My Severance Package? (Tech Chick, Mile High Rocky Mountains)
39:55 - Comment: No Financial People Ever Mentioned Roth Conversions to Me Before! (Donna, Valencia)
40:55 - Comment: Thanks for Letting Me Educate You on Retirement Plans (Debra, St Louis, MO)
42:41 - Comment: You Got the Roth 5 Year Clock Wrong (David, Michigan)
48:06 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-421

Register for our free 2023 tax planning webinar, March 29, 12pm PT
2023 Key Financial Data Guide
Complete Roth Papers Package, Including: the Ultimate Guide to Roth IRAs, the Guide to the 5-Year Rules for Roth IRA Withdrawals, and the Roth IRA Basics Guide
Episode Transcript
Ask Joe & Big Al On Air

Mutual Funds vs. ETFs, SECURE 2.0 & Capital Gains Strategies - 420 Mar 14, 2023

Are low-cost mutual funds or ETFs better investments in a tax-advantaged account? Also, more strategizing from that SECURE Act 2.0 529 plan provision, the pros and cons of selling a rental house now or holding it until you pass, and an easy-breezy self-employed retirement account that's better than a SEP IRA. Plus, will municipal bond income bump you into a higher tax bracket? Can you avoid capital gains tax by investing less aggressively over time?

Timestamps:

00:00 - Intro
00:46 - Mutual Funds vs. ETFs in a Tax-Advantaged Account? (Midwestfabs, St Paul, MN)
08:06 - SECURE Act 2.0 529 Plan Strategy (Chris, Atlanta)
14:51 - Will Municipal Bond Income Bump Me Into a Higher Tax Bracket? (Bobby, Philadelphia)
26:31 - Can I Avoid Capital Gains By Investing Less Aggressively Over Time? (Joe, Aston, PA)
33:12 - Pros and Cons of Selling a Rental House Right Now (Joe, Chula Vista)
34:48 - An Easy Breezy Self-Employed Retirement Account Better than the SEP IRA? (Steve, Las Vegas)
39:58 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-420

The SECURE 2.0 Circus: brand new YMYW TV and companion guide
Blog post: Self-Employed Tax Filing & Small Business Retirement Plans
The Ultimate Guide to IRAs
Episode Transcript
Ask Joe & Big Al On Air
(plus, cute dog photo alert! We've got Midwestfabs' dog, "Jake-from-State-Farm"!)

How to Start Planning for Retirement - 419 Mar 07, 2023

In order to retire comfortably at age 60, what should you be doing with your finances when you're in your 20s? A framework for getting started planning for retirement on today's episode of YMYW. Plus, if you're a small business with a SIMPLE IRA plan, is it stupid to save for retirement in a brokerage account rather than a traditional IRA? If you inherited money and promised to donate to charity, should you do Roth conversions? What's the most efficient way to pay financial advisor fees, and what's a good strategy for making pre-tax and post-tax retirement contributions?

Timestamps:

00:51 - A Framework for Getting Started in Planning for Retirement (Anonymous)
05:36 - I'm 24. What Should I Do to Retire Comfortably at 60? Michael, 24 (Binghamton, NY)
12:14 - I'm 32. Opened a SIMPLE IRA. Is It Stupid to Fund Brokerage Instead of Traditional IRA? (Ron Burgundy)
17:42 - I Inherited $450K, Promised to Donate to Charity. Should I Do Roth Conversions? (Allison, Northern Virginia)
23:02 - What's the Most Efficient Way to Pay Advisor Fees? (Nick, OH)
26:06 - Strategy for Pre-Tax and Post-Tax Retirement Contributions? (Dave)
29:56 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-419

Cracking the Code - Succeeding Financially at Every Age: YMYW TV & Companion Guide
Spitballing Retirement Planning in Your 30's (and even in your 20's!) - YMYW podcast 391
Top 10 Most Popular Your Money Your Wealth Podcast Episodes - Spotify playlist
Schedule a free financial assessment with Pure Financial Advisors
Episode Transcript
Ask Joe & Big Al On Air
(plus a photo of YMYW listener Nick's cute dogs!)

"Will I Ever Be Able to Retire?" - 418 Feb 28, 2023

If you've got some retirement savings but can't contribute any more, will you ever be able to retire? Joe and Big Al have three simple strategies to help you get there. Plus, how long does it take to get off of Medicare's income-related monthly adjustment amount, or IRMAA, after your income decreases at retirement, and how do you take unknown future IRMAA income limits into account when setting up your financial plan? Can you "re-do" Social Security and stop taking benefits after claiming Social Security early? Do spousal benefits change after one spouse files for Social Security? And finally, the fellas address a few corrections they've received recently regarding Medicare and safe harbor 401(k) plans. What exactly is "top-heavy" anyway?

Timestamps:

00:00 - Intro
01:02 - Will I Ever Be Able to Retire? I Have Some Savings But Can't Contribute More (Patty, NY)
06:38 - Retired, Income Dropped, Enrolled in Medicare. How Long to Get Off IRMAA? (Randy, Hb, Ca)
08:05 - How to Plan for Unknown Future Medicare IRMAA Income Limits?
10:53 - "Re-Doing" Social Security: Can You Stop Taking Benefits After Claiming Early? (Lauris, Volcano, Hawaii)
12:39 - Will Spousal Social Security Benefit Amounts Change When One Spouse Files? (Philip, Los Angeles)
15:09 - SECURE 2.0: When Must You Pay Taxes on Company Match Retirement Contributions? (Jim, Dallas, TX)
19:47 - CORRECTION: ACP Test for Safe Harbor 401(k) Plans, After-Tax Contributions (Debra, St Louis)
25:08 - CORRECTION - Medicare Test: Creditable Drug Coverage (Steve, Las Vegas)
28:56 - DUKE's Medicare Enrollment Experience (DUKE (John Wayne), Knoxville, TN)
32:54 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-418:

Retirement Readiness Guide
NAPA-net: 401(k) After-Tax Contributions Are 'Testy'
Turbocharge Your Wealth! YMYW TV & Companion Guide
Episode Transcript
Ask Joe & Big Al On Air
(Plus, YMYW Producer Andi Last video interview on the Audience Growth Podcast)

What to Do When You Get a Huge Pay Increase - 417 Feb 21, 2023

How should your financial strategy change when your income increases dramatically? We're talking like $450K one year to a million and a quarter the next? (If you guessed Roth conversions might be in the answer you'd be correct!) Joe and Big Al also spitball strategies for when your income is too high to make Roth contributions, and can you use capital gains to contribute to Roth? Can "Alligator Joe" afford to retire early, or does he need to keep gutting it out at his current job wrestling alligators? Should Catherine contribute to her 401(k) or buy company stock before she quits her day job to start a business? The fellas also spitball retirement planning involving structured settlements, inherited assets, and ACA credits, and they discuss transferring annuities to a CD vs. deferring the interest into another annuity.

Timestamps:

00:58 - Income Increased Dramatically. Should Our Retirement Tax Strategies Change? (Cookie Baron, Texas)
08:59 - Can I Use Capital Gains to Make Roth Contributions? (Aaron)
12:12 - Early Retirement Spitball: Should I Keep Gutting it Out at My Current Job? ("Alligator Joe Frazier", The Sunshine State FL)
18:11 - Contribute to 401(k) or Buy Company Stock Before Quitting to Start a Business? (Catherine, TX)
20:32 - Retirement Spitball: Income is Too High for Roth Contributions (Kelly, Owensboro, KY)
25:10 - Retirement Spitball: Structured Settlement, ACA Credits, & Inherited Assets (Kara from PA)
29:42 - Should We Transfer Annuities to CD, or Defer Interest Into Another Annuity? (Norma, Chula Vista)
34:00 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-417:

The Complete Roth Papers Package
10 Ways the SECURE Act 2.0 Changes Your Taxes and Retirement Planning (webinar)
Episode Transcript
Ask Joe & Big Al On Air

Set-and-Forget Investing, Real Estate vs. Bonds, Pension, Social Security and Medicare - 416 Feb 14, 2023

Joe and Big Al spitball on set-and-forget brokerage investments for 30-something investors, real estate as a substitute for bonds in a diversified portfolio, and options for taking a state pension with or without sick time pay. The fellas also discuss how to bridge the retirement gap until collecting Social Security, strategies for claiming spousal Social Security benefits, and whether you need to sign up for Medicare if you'd rather keep the healthcare you already have.

Timestamps:

00:49 - Set-It-and-Forget-It Brokerage Investments for a 30-Something Investor? (Chris, Scottsdale)
07:56 - Is Real Estate a Substitute for Bonds in a Diversified Investment Portfolio? (Don, VA)
12:42 - State Pension Options: $21K at Age 55 Plus $13K Sick Time, or $30K at Age 62? (Rich, NY/NC - voice message)
19:35 - Which Funds Should We Use to Bridge the Gap Until Collecting Social Security? (Jeff, San Diego)
25:29 - When Will I Receive Spousal Social Security Benefits? (Sharon)
28:37 - Spitballing a Spousal Social Security Claiming Strategy (G, Philly)
33:50 - Do We Have to Register for Medicare If We Aren't Going to Use it? (Jim Santa Cruz)
39:03 - The Derails

Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-416:

10 Ways the SECURE Act 2.0 Changes Your Taxes and Retirement Planning
Portfolio Tracker: How to Manage Your Assets at Any Age
Social Security Handbook
Medicare Checkup Guide
Episode Transcript
Ask Joe & Big Al On Air

SECURE 2.0, FIRE, Tax Arbitrage & Roth Retirement Spitball - 415 Feb 07, 2023

With the new SECURE Act 2.0 rules regarding retirement savings contributions, should your company match go into the traditional or Roth 401(k)? Joe and Big Al also discuss whether you can or should do Roth conversions when your company fails non-discrimination testing for highly compensated employees (HCEs), the mega backdoor Roth vs. the employee stock purchase plan, and they spitball a tax arbitrage strategy. Plus, a retirement spitball for a 37-year-old couple wanting to retire in their 60s, and another couple wanting to FIRE (financial independence/ retire early) - but are they screwing up and creating a huge future tax bill? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-415

Medicare IRMAA, Roth Pro-Rata, & Real Estate Strategies - 414 Jan 31, 2023

Modified adjusted income for Medicare and IRMAA and the pro-rata and aggregation rules for Roth conversions explained... clearly? Will a combat zone TSP transfer be subject to those rules? Plus, joint tenants with rights of survivorship vs. transfer on death for a brokerage account, reducing taxes on the sale of a timeshare, how much to spend on home improvements, and using a reverse mortgage instead of long-term care insurance. And wait 'til you hear Joe and Big Al's thoughts on the best way to pay the least amount of tax when you cash out your retirement savings to buy gold and silver. Show notes, many new free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-414

Spitballing Diversified Portfolios for Retirement - 413 Jan 24, 2023

How should young savers invest pensions and estimate their retirement income needs? Is going into your employee stock purchase plan a good portfolio diversification strategy? What do Joe and Big Al think of multi-year guaranteed annuities (MYGA), and dividend-paying stocks vs. ETFs? Plus, a $10.6M retirement spitball analysis, making extra mortgage payments vs. saving to a brokerage account, and contributing to Roth 401(k) vs. traditional 401(k). Also, will a 403(b) held by an insurance company be subject to separation costs or surrender fees when rolled to an IRA? And the specifics on when to file tax form 5500. Show notes, Why Asset Location Matters Guide and other free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-413

SECURE Act 2.0 & Retirement Rich, Cash Poor - 412 Jan 17, 2023

Joe and Big Al are back with a SECURE Act 2.0 recap and a proposed backdoor 529 plan strategy from the new law. Plus, is there a scenario where it makes sense to not max retirement accounts, to avoid being retirement rich and cash poor? Also, the fellas' thoughts on a break-even point for Social Security, required minimum distributions (RMD) from inherited IRAs, and of course, Roth IRA strategies: as in, the 5-year rules for Roth withdrawals, preserving Roth money and avoiding early withdrawal penalties, and Roth conversions to offset brokerage account losses. Show notes, transcript, free financial resources - including the free guide to the SECURE 2.0 Act - and to Ask Joe & Big Al On Air for your Retirement Spitball Analysis: https://bit.ly/ymyw-412

Bear Market Survival & the 5W1H of Roth Conversions: YMYW Best of 2022 - 411 Jan 10, 2023

IRA withdrawal strategies when you retire in a down market, Roth contributions vs. Roth conversions, converting now or waiting to convert to Roth in retirement, and why you'd want to lose today's tax savings and contribute to Roth in the first place, today on the best of the YMYW podcast 2022. Plus, how to know if your financial plan is on track and the funniest Derails of the year. Visit the podcast show notes for more financial resources - including the free guide to the SECURE Act 2.0 - episode transcript, and Ask Joe & Big Al On Air for a retirement plan spitball analysis of your own: https://bit.ly/ymyw-411

Retirement Planning, Investing, and Tax Reduction Made Fun: YMYW Trailer Jan 03, 2023

Welcome to Your Money, Your Wealth® podcast, with CERTIFIED FINANCIAL PLANNER™ professional Joe Anderson and Certified Public Accountant Alan "Big Al" Clopine.

Your Money, Your Wealth® is retirement planning, investing, and tax reduction made fun!

Follow YMYW on your favorite podcast app and share this trailer.

Visit YourMoneyYourWealth.com and click Ask Joe and Big Al On Air to get a Retirement Spitball Analysis of your own.

And hey, thanks for listening, because the show wouldn't be a show without you.

Your Money, Your Wealth® is presented by Pure Financial Advisors, a registered investment advisor. This show does not intend to provide personalized investment advice through this broadcast and does not represent that the securities or services discussed are suitable for any investor. Investors are advised not to rely on any information contained in the broadcast in the process of making a full and informed investment decision.

Diversification Vs. Fees: What's More Important for Retirement Investing? - 410 Dec 27, 2022

Is it better to choose low-cost index funds or to diversify investments, even if it means paying higher fees? What causes mutual fund price fluctuation? Are mid-cap funds necessary in a balanced portfolio? Joe and Big Al also talk about real estate funds vs. real estate investment trusts (REITs), and TIAA annuities vs. bonds in a retirement portfolio. Finally, we revisit some investing strategy questions that are still relevant in today's volatile markets on moving to cash in tough times, analyzing your asset allocation, and rebalancing your retirement portfolio. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-410

Who to Trust? Second Opinion Retirement Spitball - 409 Dec 20, 2022

Can you trust the opinion of just one advisor when planning for your entire financial future? Joe and Big Al spitball their second opinions for some retirement plan and Roth conversion strategies, they illustrate one way some financial advisors may be acting in their own best interests, and they explain how to determine if you're on track for a successful retirement. Plus, can you take penalty-free withdrawals from a Roth TSP to Roth IRA rollover in order to bridge the gap until age 59½? Will paying for a home remodel with Roth conversion funds avoid tax? And, should you use Roth conversion money for these purposes? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-409

Where to Save for Early Retirement? - 408 Dec 13, 2022

Asset location strategies, liquidity, and building up tax-free Roth IRA money when retiring early, how growth is taxed in taxable accounts, the pros and cons of rolling an employer retirement plan into a traditional IRA, how stock futures are determined and why stock price matters, and buying 8-week treasuries. And, if you're planning to make a killing on eBay or at your next garage sale, the fellas get into the weeds on how to maximize your tax savings. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-408

Fixed Indexed Annuities, RMDs, and Early Social Security - 407 Dec 06, 2022

We're hearing more about fixed-indexed annuities with these volatile financial markets. Is it time to reconsider? Plus, clarification on required minimum distributions (RMDs) being waived for non-spouse IRA beneficiaries in 2021 and 2022, taxation on trusts, and suggestions for a 40-year-old considering an early mini-retirement. Also, can a 62-year-old immediately withdraw Roth conversion money? Finally, a strategy to claim Social Security early while working and invest the difference in a Roth IRA, and Joe and Big Al attempt to explain family Social Security benefits without phoning it in. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-407

How to Forecast Your Expenses in Retirement - 406 Nov 29, 2022

What will you actually need to spend in retirement? Joe and Big Al explain how to really think about and calculate your retirement expenses. Plus, if you want to reduce your tax-deferred account balances, does it make more sense to do Roth conversions or reinvest? What about doing Roth conversions to a higher tax bracket than the one you'll be in during retirement? Also, the fellas explain the alternative minimum tax, how Social Security spousal benefits work, and when in the year you turn 72 you must take required minimum distributions from your retirement accounts. And finally, what should someone with no credit history who hasn't paid taxes do with a sudden $100,000 windfall? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-406

Life Insurance, Muni Bonds, and Dividend Stocks in Retirement - 405 Nov 22, 2022

Joe and Big Al discuss LIRPs, or life insurance retirement plans, they spitball whether to take full pension survivor benefits or buy a life insurance policy, and whether to sell losing stocks for even bigger losers to take advantage of the 0% capital gains tax bracket. Plus, zero coupon municipal bonds and the de minimis rule, and target date funds as part of Paul Merriman's Two Funds for Life strategy. Finally, how do dividends figure into the 4% rule for retirement withdrawals, and should that 4% come from stocks or bonds? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-405

Roth IRA 5-Year Rules: How to Withdraw Money With No Taxes or Penalties - 404 Nov 15, 2022

Joe and Big Al clarify once and for all those 5-year clocks for withdrawing money from your Roth accounts. How do the 5-year Roth IRA rules impact the taxation of dividend income? Do the 5-year rules for Roth withdrawals impact thrift savings plan (TSP) to Roth conversions as well? Plus, why contribute to a Roth in the first place and lose today's tax savings? Joe and Big Al rise to that challenge and they discuss Roth conversions and required minimum distributions from an inherited IRA. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-404

Inflation Investing, Asset Location, and Real Estate Retirement Spitball - 403 Nov 08, 2022

Following the Fed's fourth consecutive interest rate hike last week, should you be changing your investing strategy to time this inflationary market, moving from bonds to 3-year annuity CDs? Plus, Joe and Big Al spitball on asset location and Roth conversions for the in-laws, and a net unrealized appreciation (NUA) strategy for company stock in a 401(k). They also discuss whether extra home mortgage payments are part of an investment portfolio, and what real estate expenses are tax deductible. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-403

Will Your Retirement Savings Last Until You're 90 Years Old? - 402 Nov 01, 2022

Are you behind on your retirement savings? What do you need to do to catch up? If you retire in just a few years, will your money last until age 90? Based on the 5-year Roth withdrawal rules, do you need to open a new Roth IRA for each Roth conversion? Plus, Joe and Big Al spitball a health insurance, capital gains, and real estate strategy to save more money and have more wealth in retirement. Finally, they revisit the SECURE Act rules for withdrawing money from an inherited IRA, and Social Security income limits. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-402

Should Young People Save for Retirement? - 401 Oct 25, 2022

New research says some young people shouldn't save for retirement. Find out what Joe and Big Al think about that. Plus, is it tax fraud if you re-file taxes to take advantage of new student loan forgiveness? Should you invest in CDs instead of bonds, since both stocks and bonds are getting crushed right now? How can you consolidate your stock portfolio to minimize capital gains tax? Also, charitably inclined YMYW listeners want to know how to use donor-advised funds when spitballing tax planning around an IPO, and whether to do more Roth conversions or more qualified charitable distributions. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-401

Anything Stupid or Overlooked in Your Retirement Plan Spitball? - 400 Oct 18, 2022

Are there any holes in a 5-year plan to retire from the Air Force, buy a house and a plane, and become a commercial pilot? Can you claim an unpaid loan to a start-up as a tax loss, do a Roth conversion, and pay no tax? Are Roth conversions a good idea in a low-earnings year? Does it matter if you convert to Roth before or after changing custodians? What retirement savings options do independent contractors have besides the Solo 401(k)? Does it make sense to cash out a 529 college savings plan that's losing money? Plus, Joe and Big Al spitball a real estate strategy, and they discuss a state retirement account held at an insurance company. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-400

Survivor Social Security and Lowering Taxes in Retirement - 399 Oct 11, 2022

Joe and Big Al explain when and how to claim Social Security survivor benefits and how earning income impacts your benefit if you collect Social Security before full retirement age. Plus, how much should you withdraw in retirement from tax-free, taxable, and tax-deferred accounts? Also, RMDs, deciding whether to keep a life insurance policy, and of course, Roth Conversion strategies - is the backdoor Roth better for long term portfolio growth? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-399

How to Manage Financial Market Stress? With the Help of a Caddie - 398 Oct 04, 2022

As the financial markets fall and then surge, Joe and Big Al talk about market timing, reallocating retirement contributions, and portfolio rebalancing. Plus, your questions answered on estimated taxes, Roth conversions, and the logistics of inheriting IRAs and passing assets on. Finally, how is a financial advisor like a golf caddie when markets get volatile? Joe and his Pebble Beach golf caddie buddy, Big G from the Real Life Caddie Podcast, discuss how their professional knowledge and experience can help the rest of us avoid big mistakes. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-398

Spitballing Retirement Planning in Your 40's & 50's - 397 Sep 27, 2022

A compilation of some of Joe and Big Al's retirement plan spitballing specifically for those in their 40s and 50s - a critical time on the path to retirement. Is your financial plan set up so you pay as little tax as possible? Does it take volatile markets and potential future tax increases into account? Have you got a strategy nailed down for Roth conversions, or backdoor Roth, or pension options? Maybe you're making big decisions about what to do with your money between now and when you retire, like buying a house vs. saving for retirement? Are you comfortable with the retirement lifestyle you're creating? Do you know what you'll do with your time once you're permanently off the clock? Visit the podcast show notes to access free financial resources, transcript, and to Ask Joe & Big Al On Air: https://bit.ly/ymyw-397

Backdoor Roth, Investing, and Taxes - 396 Sep 20, 2022

Joe & Big Al answer your questions on, of course, backdoor Roth strategies. Y'know, to get as much lifetime tax-free growth on your investments as possible. Plus, investing strategies: does it make sense to buy a property now and rent it out until retirement? How much of a single stock in your investment portfolio can you sell and pay no capital gains tax? The fellas also explain capital loss carryovers, inherited IRAs, spousal Social Security and delayed retirement credits, required minimum distributions, and they spitball on an appropriate allocation of bonds, domestic stocks, and international stocks. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-396

Spitballing Early Retirement by the Ocean with Husband and Boyfriend - 395 Sep 13, 2022

What's the next move for a 22-year-old who wants to retire early at 50? Can another YMYW listener afford to retire by the ocean in 10 months? Can Flowergirl and her husband AND her boyfriend retire next year? Joe and Big Al also check extensive retirement spitball math sent in PDF format. Plus, what are the fellas' philosophies on single vs. married tax rates when one spouse passes, and how does high state income tax impact a retirement strategy? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-395

How to Deal With Taxes When Income Goes Through the Roof - 394 Sep 06, 2022

If a fortunate equity event or liquidity event should cause your income to skyrocket, what will that do to your taxes? Joe and Big Al spitball tax strategies to help you manage this good problem to have. Plus, Backdoor Roth, contributions, conversions, and income limits explained, converting twelve and a half million bucks to Roth, and what happens to retirement accounts when you pass - will there be a tax bill due? Kicking it off with the 7-twelve portfolio - what is it? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-394

Is Now the Time for a Roth Conversion, or Wait Until Retirement? - 393 Aug 30, 2022

Should you convert money from your pre-tax retirement accounts to Roth now, or wait until retirement, or until required minimum distributions kick in? Should a mid-30s couple do Roth Conversions or Backdoor Roth? Should a 93-year-old open his first ever Roth and start converting? What's a good retirement savings mix between pre-tax and post-tax? And the fellas do a worst-case scenario retirement spitball analysis. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-393

How to Spitball Retirement Taxes and the 4% Rule - 392 Aug 23, 2022

How do you determine how much you need in retirement when you factor in taxes, and how does the 4% rule apply? Has one YMYW listener spitballed retirement well enough to convince his wife that they can afford a new luxury truck? Can another YMYW listener take advantage of what seems to be a big opportunity to sell company stock, pay no capital gains tax, and do Roth conversions? Can Big Al's high school friend do a 1031 exchange to buy a rental property, make it his primary residence in 5 or 10 years, and pay no tax when selling? Is earned income from stock trading still taxable for Social Security if your LLC is in a trust? Finally, a compliment comes in, and Joe and Big Al assume it's for them. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-392

Spitballing Retirement Planning in Your 30s - 391 Aug 16, 2022

Setting up your saving and investing strategies when you're in your 30s can put you on a good path to meeting your retirement goals. We're revisiting Joe and Big Al's financial spitballing over the last couple of years specifically for savers and investors in their 30s and even 20s, some of whom want to retire early. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-391

Working After Retirement and Wealth Gifting Strategies - 390 Aug 09, 2022

When you retire and when you actually stop working may be two different things. How can you get a raise when you're working for a startup in retirement? Should you do Roth conversions before or after you quit working? Plus, find out what Joe and Big Al think about a 529 and series I bond gifting strategy, and using whole life insurance to transfer wealth to the kids. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-390

Save for a Home or Save for Retirement? - 389 Aug 02, 2022

Should you save for a house down payment or invest for retirement? How much long term capital gains tax do you pay on a rental property when you sell it after 20 years, and how does a 1031 exchange work? Also, opening a Roth IRA with the Backdoor Roth strategy, and the 5 year Roth withdrawal rules explained. Plus, a couple retirement spitball analyses: are you saving too aggressively for retirement? Can you avoid the Medicare IRMAA, or income related monthly adjustment amount, and high taxes from required minimum distributions? Show notes with annual podcast survey, free financial resources, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-389

Pay Tax on This Move Now to Potentially Have More to Spend Later - 388 Jul 26, 2022

The time may be right for a giant Roth IRA conversion, especially now while the market is down, to potentially give you more money to spend in retirement. How does that work with long-term capital gains and dividends, and how much should you convert to Roth, and when, and how? Plus, deciding how to invest 529 plan college savings, whether to save to pre-tax or post-tax retirement accounts, and the ever-popular Backdoor Roth strategy. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-388

A Model Retirement Plan Spitball Analysis - 387 Jul 19, 2022

Learn how to craft a retirement plan email question that'll get you a model retirement spitball analysis. Plus, when should you contribute to Roth IRA, and when and how much of a Roth Conversion should you do? Is it hypocritical to prioritize investment returns over your conscience and values? Joe and Big Al talk ESG, or environmental, social, and governance investing, and they evaluate a strategy to keep taxes low while helping your kids buy a house. Finally, your comments about YMYW. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-387

Should We Hold Off on Retiring Until the Markets Recover? - 386 Jul 12, 2022

When the financial markets are down, should you postpone retirement? When inflation is up, should you change your investments and pile into things like value and commodities? Plus, the ever-popular retirement spitball analysis: an early retirement plan, Medicare, Social Security, TSP, and Roth conversions, and when and how business owners should convert $5.5M to Roth IRA. Also, if excess 2021 Roth contributions were returned, can you file last year's taxes now without penalty? Finally, what's the difference between a collective investment trust and regular mutual funds? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-386

Bonds and Series I Bonds, High Inflation, and High Interest Rates - 385 Jul 05, 2022

Inflation is high, interest rates are high, and the financial markets are volatile. Are bonds and series I bonds good investments or bad investments right now? How do bonds fit into your overall retirement portfolio? Plus, variable annuities, evaluating the long-term value of Roth contributions vs. Roth conversions, what if anything can be done about losses in an after-tax 401(k), helping adult kids buy a home, and drinks in the Derails. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-385

Can We Retire Soon? Retirement Spitball Analysis - 384 Jun 28, 2022

"Are we on track for retirement?" The ever-popular YMYW Retirement Spitball Analysis is all based on that simple question. Joe and Big Al spitball retirement for listeners planning to retire in just a few years, wondering if they should save to pre-tax or post-tax accounts, and strategizing around long-term capital gains, dividends, and Roth conversions. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-384

Where to Find Retirement Income When the Stock Market Freaks Out - 383 Jun 21, 2022

Equitable accumulators, cash management accounts, and Social Security: with today's market volatility, how can you squeeze a few more dollars of income out of your retirement savings? Any reason not to use a robo-advisor for decumulation, in other words, spending down those savings? Plus, a pension retirement spitball follow-up, and is it possible to avoid tax liability on a lump sum withdrawal from a 401(k)? Finally, is Joe's marriage the canary in the Coors Light Party Ball for YMYW? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-383

Where Should You Save for Retirement? Where Does Real Estate Fit? - 382 Jun 14, 2022

If you own houses in your self-employed, self-directed solo 401(k), is converting a house a year to Roth to avoid required minimum distributions (RMDs) a good strategy? What's an individual coverage health reimbursement arrangement (ICHRA) and is it a good healthcare option for those with C-corporations? When putting away retirement savings, should you contribute to a Roth IRA, a brokerage account, a 401(k), or your employee stock purchase plan (ESPP)? When it comes to step-up in basis, how do you determine the past fair market value of a home? And finally, what happens if you retire before your construction loan becomes a permanent mortgage? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-382

Don't Retire Until You Can Answer These Five Practical Questions - 381 Jun 07, 2022

Joe Anderson, CFP® and Big Al Clopine, CPA are all about having a plan for retirement. Using examples from past YMYW episodes, they cover five questions you need to answer before you retire - so you can stay retired. Show notes, free financial resources to help you answer each question, and Ask Joe & Al On Air: https://bit.ly/ymyw-381

1. Can We Afford to Retire? 2. When Should We Claim Social Security? 3. How Can We Reduce Taxes in Retirement? 4. Are We Prepared for Medical Costs? 5. How Will We Fill Our Time?

How to Ditch a Bad SIMPLE IRA? What's a Prohibited Transaction? - 380 May 31, 2022

Is there a way to get out of a bad SIMPLE IRA and stash cash in a tax-free Roth account? Can an owner of a company, that's being sold to another company, load up a Roth account with company shares before the sale, and have a big chunk of cash happily growing tax-free? (What exactly are disqualified persons and prohibited transactions?) When designating beneficiaries of an annuity in a community property state like California, does state law or the annuity owner determine the beneficiary? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-380

6 Money Strategies for Down Markets Depending on Your Goals - 379 May 24, 2022

As bear market territory freaked out some investors, YMYW listeners were a bit more chill as Joe and Big Al spitballed on their specific strategies to manage the decline: does it make sense to move to cash inside your retirement account? How do down markets impact Roth Conversion decisions for older investors? What should your asset allocation be now, during market volatility, if you're expecting a future windfall? How should you manage the relationship with your financial advisor if they buy high and sell low in your investment portfolio? Should you leave a partially vested pension to grow, or withdraw the money now and convert to Roth? What's the best way to withdraw from an IRA in a down market? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-379

Is My BF BSing Me on RMDs? Required Minimum Distributions Explained - 378 May 17, 2022

Required minimum distributions: how do they work, when do you have to take them, and do Roth IRAs have RMDs too? Plus, were the fellas being misleading when they talked about claiming Social Security early vs. late if you save and invest the benefits? Listen for their rebuttal. When you change 401(k) custodians, is it a transfer, or a whole new plan? Can you convert your entire 401(k) to Roth, and should you? Finally, If you're worried about high tax brackets in retirement, should all your contributions now go to Roth? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-378

Roth IRA, 457, TSP, and Retire Early Spitball - 377 May 10, 2022

Joe & Big Al talk strategy for converting to Roth and paying tax from the IRA when you have limited funds, eliminating required minimum distributions (RMD) on a Roth 457 and avoiding the 5-year Roth clock, and Roth 457, Roth IRA, and Roth TSP. Plus, the fellas spitball pension options, retiring early, and an intricate and potentially risky deferred compensation strategy. Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-377

Self-Employed Retirement, Fixed Index Annuities, and Investment Property - 376 May 03, 2022

How does Social Security work for self-employed small business owners? Is there a solo 401(k) that allows after-tax contributions? How much cold, hard cash should you keep on hand? Why do advisors suggest buying a fixed indexed annuity, and how do qualified charitable distributions work? Finally, is it a good idea to pre-pay the mortgage on a real estate investment, and how do you calculate the tax on a home you inherited? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-376

Roth Conversion Retirement Spitball Analysis - 375 Apr 26, 2022

Does it make sense to do larger "Calvin Johnson" (megatron, aka mega backdoor) Roth conversions when the financial markets are way down? Should you convert to Roth now, or in retirement? How do you spitball the right amount to have in 529 plans for education savings? And are the rules for doing a backdoor Roth the same if you're married filing separately? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-375

Annuities, Social Security, and Real Estate Taxes - 374 Apr 19, 2022

When is it appropriate to buy an annuity? Joe and Big Al run a retirement annuity spitball analysis. When might it make sense to take Social Security early, and what are the rules for collecting survivor Social Security benefits? Finally, how does net investment income tax (NIIT or the Medicare surtax) on long term capital gains impact a house sale? Is it possible to do a 1031 exchange from rental real estate in Utah for investment property in California? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-374

Can We Retire Early? Investing and Retirement "Rothification" - 373 Apr 12, 2022

Will the Senate pass the SECURE Act 2.0, and will it require a Roth option for retirement savings? Plus, "pandemic unemployment" from the CARES Act and the earned income tax credit. Next, are you eligible to make Roth contributions, and should you contribute only to Roth for retirement? Then, the pros and cons of consolidating retirement accounts, and some early retirement spitball analyses. When you plan to retire early, should you invest in dividend paying stocks or real estate? And finally, is the bucket investing strategy really that complicated? Podcast show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-373

Retirement Spitball: Social Security, Pension, and Self-Employed - 372 Apr 05, 2022

Spitballing retirement for a police officer turning teacher, a self-employed small business owner, an early retiree with an employee stock ownership plan (ESOP) wanting to do Roth conversions and withdraw 5 or 6% in retirement, and a pension and Social Security analysis. Plus, how many months of expenses should you save in your emergency fund? Also, you may know where Ric Edelman and Dave Ramsey stand on 15 vs. 30 year mortgages and using cash vs. credit, but what does YMYW think? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-372

When Must You Pay Roth Conversion Taxes? - 371 Mar 29, 2022

When do you have pay the taxes on a Roth IRA conversion to avoid any IRS penalties? Was it a mistake to convert to Roth IRA? What percentage of your assets should be in tax-free, tax-deferred, and taxable accounts to give maximum flexibility in retirement? And finally, do Roth conversions count as income toward your eligibility to contribute to a Roth, and how will a pension be taxed? Podcast show notes, episode transcript, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-371

Taxes and Real Estate Investing Explained - 370 Mar 22, 2022

Can multiple rental property losses be written off against other properties or income? What are the pros and cons of putting investment property in an LLC? How do you get the best tax breaks on rental real estate? How does real estate depreciation work? What do you need to think about when turning your primary residence into a rental property? Is a home equity line of credit (HECM, reverse mortgage) a good idea? Also: a complicated property inheritance and self-funding long term care insurance. Financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-370

Should You Claim Social Security Early? - 369 Mar 15, 2022

What part do taxes play in deciding to claim Social Security early? If Social Security creates too much provisional income so that you have to pay tax on your Social Security benefits, does it make sense to claim early? If you apply for Social Security at age 70 but could've been taking spousal benefits, are you owed that money? How long was the recovery from the 1929 stock market crash, really? Do higher yield investments early in retirement offset sequence of returns risk? Plus, a listener takes issue with YMYW's dollar-cost averaging discussion, and Joe's big news in the Derails. Transcript, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-369

Why Is It So Difficult to Time the Market? - 368 Mar 08, 2022

How statistically and practically difficult is market timing? Plus, Backdoor Roth vs Roth conversions, rules, limits, and strategies for 401(k) and IRA contributions, moving retirement money between custodians like Vanguard and Fidelity, and negative but entertaining listener comments. But first, should a $100,000 inheritance be invested in tax deferred, taxable, or tax free accounts? Also, factors to consider when choosing large cap value funds. Show notes, financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-368

Dollar-Cost Averaging, Small Cap, and Stable Value Funds - 367 Mar 01, 2022

What are dollar-cost averaging and reverse dollar-cost averaging? Joe and Big Al explain as they answer questions about paying Medicare premiums with HSA funds, and ETFs vs mutual funds when dollar-cost averaging into small-cap value funds. Plus, why would you want to reduce the stock allocation in your emergency fund, and should a stable value fund be part of your portfolio? Is it possible to "re-identify" an inherited IRA as a spousal IRA to change the RMD calculation? Is the section 162 executive bonus plan just whole life insurance? And finally, Joe's past comes back to haunt him with 9 cats, a neurotic beagle, and 200 IRAs. Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-367

Roth Conversions vs. Roth Contributions - 366 Feb 22, 2022

Should you use Roth contribution money to pay Roth conversion tax instead? Does the IRS really penalize ineligible Roth contributions? How will a mega backdoor Roth be taxed, and will the step transaction doctrine apply? Are family Social Security benefits affected if the spouse works? Plus, spitballing retirement pension options, and your comments. Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-366

Real Estate Investing: What Are Cash-on-Cash and Cap Rate? - 365 Feb 15, 2022

What is a cap rate? What does cash-on-cash return mean? Joe and Big Al on rental real estate investing as an early retirement income source. Plus, the stacking rule, the foreign earned income exclusion, and taxes and working - or not - after you retire. Finally, at what point are you saving too much to pre-tax accounts, and is it a good idea to convert to that post-tax Roth before the tax brackets change? Financial resources, transcript, Ask Joe & Al On Air: https://bit.ly/ymyw-365

Covered Call Investing Strategies Explained, RMDs, and Social Security Taxation - 364 Feb 08, 2022

Covered calls, preferred stocks, interest on series I bonds, required minimum distributions (RMD) from your retirement accounts and when they must begin, using retirement savings at age 72 to buy a home, calculating the highest possible Social Security benefit, and how it may be taxed. Plus, listener comments about YMYW and Andi's record collection! Show notes, free resources, transcript, Ask Joe & Al On Air: https://bit.ly/ymyw-363

Stock Acquisition, HSA, AMT, TSP, RSU, and Trust as Retirement Beneficiary - 363 Feb 01, 2022

Should a trust be the beneficiary of your retirement accounts? Are withdrawal restrictions and required minimum distributions (RMD) reasons to transfer out of the thrift savings plan (TSP) at retirement? Plus, alternative minimum tax (AMT) explained, and strategies for health savings account (HSA) contributions and restricted stock units (RSU). Free financial resources, Ask Joe & Al On Air: https://bizlink.to/ymyw-363

Early Retirement, Roth Conversion Tax: YMYW Best of 2021 - 362 Jan 25, 2022

Early retirement, backdoor and mega-backdoor Roth conversions, paying tax on a conversion, asset location... the important topics from our most popular podcast episodes and YouTube videos of 2021. Plus, "impactful" listener comments and the funniest Derails of 2021 (in real time!) Show notes, financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-362

Financially Able But Afraid to Retire - 361 Jan 18, 2022

The psychology of retirement: what if you've saved enough and you're financially ready to retire, but you're paralyzed by the idea of no longer earning and saving? Plus, a Roth conversion strategy when your income is too high. How to know if it pays for you to convert & how much, and should you contribute to a rollover IRA before or after leaving a job? Finally, should you purchase long-term care insurance or self-insure? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-361

Should You Invest in the Stock Market or Buy Real Estate? - 360 Jan 11, 2022

You've saved money for a house downpayment. Should you invest it in the stock market until you're ready to buy that property? Should a young saver take as much investing risk as possible, or buy a condo? Plus, the tax-efficiency of robo-advisor brokerage account withdrawals, backdoor Roth conversions under the Build Back Better Act, using a charitable remainder trust to avoid inherited IRA tax under the SECURE Act, and your comments. Show notes, free resources, Ask Joe & Al: https://bit.ly/ymyw-360

Social Security Benefits for Spouses, Ex-Spouses, and Survivors - 359 Jan 04, 2022

Learn how to get the biggest Social Security payment possible, whether you're married, divorced, or entitled to survivor benefits. Can you still file and suspend? What's a restricted application? What does "deemed" mean? Plus, the little-known family Social Security benefits. The first YMYW podcast of 2022 is a compilation of answers to all of your most recent spousal Social Security questions. Visit the show notes, download free financial resources, and Ask Joe & Al On Air: https://bit.ly/ymyw-359

Roth Conversions, the Rule of 55, and Retirement Withdrawal Regrets - 358 Dec 28, 2021

Spitballing Roth conversions: a conversion and pension lump sum strategy, converting vs. harvesting 0% long term capital gains, and how to avoid double taxed Roth conversions. Plus, how to allocate assets when using the Rule of 55? Do retirees regret not spending more in retirement? Will paying a thrift savings plan loan with real estate income avoid income tax? Will assets be better protected against litigation in a TSP or an IRA? Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-358

Does the 5 Year Rule Apply to Each Roth Conversion? - 357 Dec 21, 2021

Does the 5-year Roth clock start with every Roth conversion? Plus, a Social Security, Medicare, IRMAA, Roth conversion spitball, a self-employed retirement savings and tax planning spitball, and Delaware Statutory Trusts, security-based loans, charitable remainder trusts, and other charitable giving strategies explained. Also, will your portfolio grow faster with the help of a financial advisor? Visit the show notes for free financial resources and to Ask Joe & Al On Air: https://bit.ly/ymyw-357

Spitballing Retirement and the Build Back Better Tax Proposal - 356 Dec 14, 2021

Should those in the 35% tax bracket contribute to traditional 401(k) or Roth 401(k)? Should a self-employed cryptocurrency investor do Roth conversions or tax gain harvesting? Also, a retirement spitball for a couple, age 35, wanting to retire with $5M at age 60. Plus, do the SECURE Act rules for required minimum distributions (RMDs) apply when inheriting an inherited IRA? Finally, comments on the latest Build Back Better Act. Show notes, financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-356

Saving and Investing for Retirement with Company Stock, Bonds, and VTSAX? - 355 Dec 07, 2021

How much company stock is too risky? Can I bonds be the "cash" in a portfolio? Would saving to a brokerage instead of 401(k) or 403(b) ever make sense? How should a self-employed investor in Vanguard's Total Stock Market Index Fund (VTSAX) get retirement-ready? How to pay for new home construction and keep the earned income and child tax credits? Should Roth conversion funds come from retirement, brokerage, or Social Security? Show notes, financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-355

Retirement Pension Lump Sum or Monthly Annuity Payment? - 354 Nov 30, 2021

Should you take your pension all at once in a lump sum when you retire or spread it out over monthly annuity payments? What if the lump sum choice requires moving your pension to an investment plan? Or maybe your only pension options are either 10-year period certain or joint with rights of survivorship? All of these pension spitball analyses are compiled into this single episode to help you choose between your own pension options. Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-354

Retirement Spitballing, Social Security, and Hiring & Ghosting Financial Advisors - 353 Nov 23, 2021

How does the "Buy, Borrow, Die" strategy of the uber-wealthy work? Stacking capital gains vs. Roth conversions, contributing to a non-deductible IRA vs. a brokerage account, and minimizing tax when a trust is the TSP beneficiary. Also, why delay Social Security to age 70 if you don't need the money, and estimating benefits with a future salary of $0. Finally, can you "ghost" an advisor? Should you hire a financial advisor near you? Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-353

Dividends, Asset Classes, and Diversification: How to Invest for Retirement? - 352 Nov 16, 2021

Can your investment portfolio be over diversified? How do dividends and net unrealized appreciation (NUA) work? How will ownership inequality in the stock market impact future returns for most investors? What do Joe & Big Al think of target date funds? Plus, the YMYW podcast is now on video! Watch the fellas spitball on annuities, bonds, long-term treasuries, risk tolerance, and the buckets of money investing strategy. Show notes, video clips, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-352

Estate Planning, Social Security, and TSP to Roth Conversions - 351 Nov 09, 2021

Is there a step up in basis on (and advantage to) a joint tenants with rights of survivorship brokerage account? Is a charitable remainder trust a good way to liquidate property? Is there a point to Roth conversions when leaving your estate to charity? Should you name your trust as beneficiary on retirement accounts? When to draw from Social Security, pension, and annuity in retirement? Plus, Roth conversions from a thrift savings plan. Show notes, resources, Ask Joe & Al On Air: https://bit.ly/ymyw-351

Spitballing the Sequence of Retirement Savings - 350 Nov 02, 2021

In what order you should contribute into which accounts for retirement? Joe & Al explain the reasoning behind the sequence of retirement savings and where a health savings account (HSA) fits. Following some retirement plan spitball analyses and Roth conversion strategizing, the fellas explain whether capital gains are taxed progressively, how required minimum distributions are taxed, & they revisit indexed universal life insurance. Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-350

How to Pay the Tax on a Roth Conversion - 349 Oct 26, 2021

Learn the basics of Roth IRA conversions, how to calculate the tax on a Roth conversion, when to pay the tax, and more. Plus, ideas for what to do with unused 529 plan education savings funds, rules for 401(a) accounts, understanding the alternative minimum tax, the latest tax proposals, how to calculate employer solo 401(k) contributions - and that's just the tip of the iceberg. Visit the podcast how notes for free financial resources and to Ask Joe & Al your money questions: https://bit.ly/ymyw-349

Medicare, Social Security, and FIRE Early Retirement - 348 Oct 19, 2021

How to calculate modified adjusted gross income (MAGI) for Medicare IRMAA, Social Security benefits when you're planning to FIRE (Financial Independence / Retire Early), family Social Security benefits for those with minor children, and a strategy to qualify for the Obamacare ACA subsidy. Plus, Roth conversions prior to early retirement, and untangling stock options, long-term incentives (LTI), and restricted share units (RSU). Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-348

What's the Right Mix of Stocks and Bonds for Your Investment Portfolio? - 347 Oct 12, 2021

Asset allocation is the delicate balance of stocks, bonds, and other assets in an investment portfolio. What allocation is best for your retirement needs? What mix of domestic and international stocks is best? Is a 90/10 equities to fixed income mix crazy in a $10M portfolio? Should Dad be at 90/10 or 60/40? Can pension & Social Security count as a bond allocation? Plus, legacy tax planning: how to avoid confiscatory estate taxes? Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-347

Buying and Selling Your House or Real Estate - 346 Oct 05, 2021

How do you estimate net investment income tax when selling your primary residence? Is the all-in-one mortgage a temporary solution when buying a house before selling your current home? Also: buying property in California with your kids, and should you pay the mortgage or save for retirement? Plus, what's the best way to pay credit card debt? Do corporations really pay no taxes? Can you contribute to both Roth IRA and Roth 401(k)? Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-346

Working or Retiring Abroad and Early Retirement Spitball - 345 Sep 28, 2021

Retiring overseas and foreign earned income exclusion eligibility, using your tax refund for a back door Roth conversion, and working abroad and contributing to a health savings account (HSA). Plus, should you contribute to Roth, pre-tax accounts, or brokerage for early retirement? Are substantially equal periodic payments (SEPP) good to bridge the gap between retiring early and age 59.5? Is it ever a good time to time the market? Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-345

It Could Be Over for the Mega Backdoor Roth IRA - 344 Sep 21, 2021

Joe & Big Al outline the House Ways and Means Committee's sweeping tax proposal that would impact Roth contributions, Roth conversions, RMDs, the backdoor Roth IRA and mega backdoor Roth (Megatron), marginal and capital gains tax rates, wash sale rules, and more. Plus, safe retirement income and withdrawal strategies, when NOT to do a Roth IRA conversion, and solo 401(k) retirement savings for self-employed small business owners. Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-344

HELOC, All-in-One Mortgages, and What to Do With Old Life Insurance Policies - 343 Sep 14, 2021

What is a home equity line of credit? Is a HELOC better than a traditional mortgage? What are all-in-one mortgage loans? Does it make sense to buy a condo, or keep investing for retirement? Next up Joe and Big Al spitball ideas on what to do with old whole life insurance policies. Plus, ABLE accounts for individuals with disabilities, and should you claim Social Security benefits before or after moving to a no income tax state? Free financial resources in the podcast show notes: https://bit.ly/ymyw-343

Roth 401(k), Conversions, RMDs, and Cap Gains - 342 Sep 07, 2021

How to calculate Roth conversions to reduce taxes at required minimum distribution age? What are the rules for RMDs from Roth 401(k)? How does the 5 year Roth clock factor into a decision to leave money in an old Roth 401(k) or roll it to a new Roth IRA? Do reinvested dividends count as Roth contributions? Do capital gains count towards the capital gains income bracket? IRA contributions for minors and the unemployed, and how would you spend lottery winnings? Podcast show notes: https://bit.ly/ymyw-342

Early Retirement Spitball Analysis - 341 Aug 31, 2021

Some YMYW listeners have had enough of the 9 to 5 and are ready to punch early. Joe & Big Al spitball on whether they're financially ready for a long, early retirement. Plus, the ever-popular Roth IRA conversions: how much to convert to Roth, when and how to pay tax on a Roth conversion, and why not pay tax on Roth conversions out of the retirement account you're converting from? Podcast survey (final day!), financial resources, Ask Joe & Big Al On Air in the podcast show notes: https://bit.ly/ymyw-341

Where to Locate Assets for Tax Efficiency Without Compromising Growth? - 340 Aug 24, 2021

Asset location: how to position assets to pay less tax without sacrificing investment growth? Should young folks contribute all of their retirement savings to Roth accounts? Also, conversations (not advice) on a self-employed defined benefit plan vs. pass-through profits, gifting tuition for education, Roth conversions with a special needs child in mind, a correction on inherited Roth IRAs, and listener comments. Podcast survey, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-340

Should We Do a Roth Conversion? - 339 Aug 17, 2021

Moving money from tax-deferred retirement accounts to accounts with lifetime tax-free investment growth: should you do Roth IRA conversions? Before marriage? From a 403(b)? When and how much to convert? Convert aggressive funds first? What about the ACA subsidy? Will paying Roth conversion tax ruin early retirement? And something completely different: Joe & Big Al's take on Ric Edelman's "pay off the mortgage" suggestion. Podcast survey, transcript, free resources, Ask Joe & Al: https://bit.ly/ymyw-339

What to Do When You Own Too Much of One Stock - 338 Aug 10, 2021

Ways to diversify concentrated stock positions, like using a donor-advised fund. How does the IRS know if a required minimum distribution is a qualified charitable distribution? From which pool of money should you pull extra retirement income? Also, structured notes, & paying Grandma for daycare without impacting taxes on her pension - lump sum or monthly payments? Finally, thoughts on starting a career in financial planning. Podcast survey, transcript, resources, Ask Joe & Al: https://bit.ly/ymyw-338

Is It Crazy to Be Happy Paying Tax on Massive Stock Market Gains? - 337 Aug 03, 2021

Is it better to pay tax on $5 million than on $1M? Also, an asset location strategy to lower RMDs and taxes but still maintain portfolio growth, and an argument against Roth IRAs. Is it valid? Plus, what counts as contributions if you withdraw from Roth after 5 years? Why not pay the tax on a Roth conversion out of an IRA? Roth conversions vs. the medical insurance ACA subsidy, and what? Joe, arrogant?! Podcast survey, free resources, transcript, ask money questions: https://bit.ly/ymyw-337

How to Spitball Your Most Tax-Efficient Retirement Withdrawal Strategy - 336 Jul 27, 2021

Spitballing tax-efficient retirement withdrawals, savings, Social Security, and required minimum distributions (RMD). Plus, leveraging whole life insurance, and is investing 15% of an all-stock portfolio in preferred stocks too risky? First, Joe and Big Al break down the mechanics and safety of doing a 401(k) to IRA rollover. Visit the podcast show notes to access the transcript, free financial resources, and to ask your money questions: https://bit.ly/YMYW-336

Which States Are the Most Tax-Friendly in Retirement? - 335 Jul 20, 2021

Which states are best for retirement taxes? When moving to a state with a lower cost of living, is it wise to take on mortgage debt to invest in the market? Does it make a difference if you do a Roth conversion before or after moving states? Plus, is it better to do Roth conversions with ETFs or mutual funds? Is 0% long-term capital gains a hoax? Also, ABLE accounts for those with disabilities, and healthcare costs vs. taxes. Financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/YMYW-335

Are We On Track for Retirement? Financial Plan Spitball Analysis - 334 Jul 13, 2021

Spitballing retirement readiness for Sean and for Little Al who has UK retirement funds and is desperate to quit work now. Plus, how can Doug do some tax arbitrage with pensions, Roth conversions, and Social Security? Can Mary switch to her ex-spouse's Social Security benefit? First, Tyler has questions about restricted stock units (RSUs) and net unrealized appreciation (NUA). Access the transcript and free financial resources, and Ask Joe & Big Al On Air in the podcast show notes: https://bit.ly/YMYW-334

Are Financial Advisors Really Worth the Money? - 333 Jul 06, 2021

Do you need a CERTIFIED FINANCIAL PLANNER™ professional? Is a financial advisor worth hiring? What does a fee-only fiduciary do, anyway? We get these questions frequently, and now you can listen to Joe & Big Al's answers from 2016 to the present, all in a single episode. Plus, how to measure CFP® performance, and when it's time to part ways with your financial planner. Access the transcript and free financial resources, and Ask Joe & Big Al On Air, all in the podcast show notes: https://bit.ly/YMYW-333

Roth Conversions, Medicare, and Required Minimum Distributions - 332 Jun 29, 2021

Do Roth IRA conversions increase Medicare premiums? How can you convert to Roth and stay below the IRMAA threshold (that is, Medicare's Income-Related Monthly Adjustment Amount)? Also, a Roth conversion strategy to account for RMDs, those 5-year rules for withdrawing from your Roth depending on whether you're over or under age 59 and a half, and "how much should I have in a Roth to be in a low tax bracket in retirement?" Financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/YMYW-332

What is the Best Age to Retire, Financially Speaking? - 331 Jun 22, 2021

Financially, what's the ideal retirement age? Are Roth conversions to the 37% tax bracket a good idea when you've achieved FAHR (financial abundance, happily retired)? Should you stop investing and start saving cash when approaching retirement? You're maxing retirement accounts, should you save to a deferred comp plan too? Is the employee stock purchase plan too many eggs in one basket? And finally, how to pay for long-term care insurance? Podcast show notes, Ask Joe & Big Al On Air: https://bit.ly/YMYW-331

Has the Government Ever Reduced Social Security Benefits? - 330 Jun 15, 2021

Have Social Security payments ever been cut for those already receiving them? Plus, survivor benefits, the Windfall Elimination Provision (WEP), and CalPERS. Also: what retirement accounts should you save into in what order? How should you withdraw from a brokerage account in retirement? And paying the tax on a Roth conversion, overfunding a 529 plan for education, and mortgage refinancing and interest deduction. Access the transcript and financial resources, ask Joe & Big Al On Air: https://bit.ly/YMYW-330

How to Protect Investments Against a Stock Market Crash? - 329 Jun 08, 2021

Strategies to protect your portfolio from a stock market crash: put options, collars, non-correlated alternative investments, and tax-managed buy-and-hold. Also: how to measure financial advisor performance? How does tax-loss harvesting work? Are health savings accounts (HSA) tax-free? Is alternative minimum tax (AMT) a concern when moving Roth to an annuity? And how to get your MIL not to smoke in your car? YMYW podcast show notes, free financial resources, transcript, Ask Joe & Al: https://bit.ly/YMYW-329

Should People in High Tax Brackets Save in Roth Retirement Accounts? - 328 Jun 01, 2021

Roth 401(k) contributions and "Megatron" (er, mega backdoor) Roth contributions for highly compensated employees, and the Roth conversion strategy of filling the tax bracket. Plus, moving a pension to an investment plan, owning real estate in a self-directed IRA, paying off the mortgage vs. refinancing your house, spousal vs. survivor Social Security benefits, and rolling a whole life insurance policy to a variable annuity. Access the YMYW podcast show notes and Ask Joe & Al on air: https://bit.ly/YMYW-328

How to Avoid a Tax Time Bomb: Retirement Plan Spitball Analysis - 327 May 25, 2021

Maxing out Roth IRA, 457, and HSA - check. Pension - check. What else do you need for retirement planning? How do pension and Social Security fit into your fixed income portfolio mix? Should you be more aggressive with Roth conversions? Is a 5% equities growth rate good for early retirement plans with inflation? Will a Spousal Lifetime Access Trust (SLAT) protect assets from a tax time bomb? Plus a SECURE Act 2.0 overview. Transcript, financial resources, ask your money questions at https://bit.ly/YMYW-327

How to Get Tax-Free Growth on Investments for Life - 326 May 18, 2021

Learn to rack up tax-free Roth retirement income: Roth IRA vs. Roth 401(k), paying the tax on a Roth conversion, avoid violating the 60-day rollover rule on a mega backdoor Roth, and Roth IRA contributions when receiving restricted stock units (RSU) in retirement. Plus, moving money from solo 401(k) to IRA before age 59.5, suggestions for a CFP® to be, and matching your umbrella insurance policy to your net worth. Access the transcript & financial resources, ask your money questions: https://bit.ly/YMYW-326

Capital Gains Tax Vs. Ordinary Income Tax Explained - 325 May 11, 2021

"Can you explain how long-term capital gains are 'stacked on top' of ordinary income?" Here are all the YMYW capital gains tax vs. ordinary income tax discussions, together in a single episode, to help you craft a tax-efficient strategy for managing dividends, Roth conversions, and paying less capital gains tax. Will your taxes be going up? Subscribe to the YMYW podcast and newsletter for the latest updates. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-325

Which Asset Classes Are Good Investments to Hedge Against Inflation? - 324 May 04, 2021

Your latest investing strategy questions answered: are gold, real estate investment trusts (REITs), international and small-cap value funds good inflation hedges? Besides the S&P 500, what sectors or asset classes should you invest in for long-term portfolio diversification? Should you buy bonds? How should an 18-year-old invest the money in a Roth 401(k)? Also, how can you get out of a non-qualified annuity? Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-324

Real Estate: Should We Sell Rental Property to Buy a Primary Residence? - 323 Apr 27, 2021

Spitballing a real estate strategy: sell investment rental properties to buy a home, use restricted stock units (RSU), or both? Plus, is it worth it to hire a financial advisor? Is it a good idea to do Roth IRA conversions to the top of your tax bracket each year? How can you move non-deductible IRA money to Roth IRA without paying taxes again? And a cautionary tale about Roth conversions and stimulus payments. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-323

Pay Down the Mortgage or Buy Long Term Care Insurance? - 322 Apr 20, 2021

Fielding emails on a wide range of personal finance topics: ex-spouse Social Security benefits, paying the mortgage or buying long-term care insurance, how the FIRE community uses the Roth conversion ladder, tax rules for sole proprietors hiring minors, using excess 529 plan education savings, paying taxes or paying back a Coronavirus Related Distribution, and when to file form 8606 to report IRA contributions. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-322

Inflation, Variable Annuities, Real Estate: How to Invest Against Risk - 321 Apr 13, 2021

Is selling rental property to buy a variable annuity a good risk management strategy against sequence of return and interest rate risks? Small-cap vs. emerging markets: which has better risk-adjusted returns for market volatility? Are eREITs (non-traded real estate investment trusts) a good retirement investment? Is RPAR Risk Parity ETF a good inflation hedge? Should you do tax gain harvesting in declining financial markets? Access the transcript and resources, ask money questions: https://bit.ly/YMYW-321

Early Retirement: Can You Afford to Retire Now? - 320 Apr 06, 2021

William has investing experience, money in the bank, and a retirement plan. Is he ready for early retirement at age 59.5? Plus, BRRR real estate investing and Roth IRA, Backdoor Roth conversions, and "Megatron" Roth contributions. Also, capital gains vs ordinary income, and are restricted stock units (RSU) ordinary income? Do they impact Social Security benefits? When can you collect spousal Social Security? Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-320

Roth IRA Excess Contributions and the Pro-Rata Rule - 319 Mar 30, 2021

Recharacterization of excess Roth IRA contributions, converting post-tax contributions to Roth 401(k), and the pro-rata rule. Plus, target date fund ladders? Also, investing 529 plan money, section 199A dividends from real estate investment trusts (REITs), and how Matt Stafford should save for retirement with his new $34M LA Rams contract (just in case you're expecting a football player's salary anytime soon.) Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-319

Firefighters' Retirement Plan Spitballing, Annuities, and RMDs - 318 Mar 23, 2021

Spitballing firefighters' retirement: deferred option retirement plans (DROP), HSA (health savings) vs. HYSA (high yield savings), and hear why YMYW always comes back to backdoor Roth IRA. Speaking of Roths, can you do a Roth conversion ladder with inherited IRA money? The fellas also break down required minimum distributions (RMDs) and they talk (or in Joe's case, rant) about variable annuities and indexed annuities. Access the transcript & financial resources, ask money questions: https://bit.ly/YMYW-318

Charitable Giving and Roth Conversion Retirement Tax Strategies - 317 Mar 16, 2021

How to make the most of a retirement strategy that involves a thrift savings plan, Roth IRA conversions, and charitable giving from a donor-advised fund or a QCD. Also, how to calculate multi-year Roth conversions, and do you lose compound interest when doing Roth conversions? Plus, thoughts on closed-end funds, a variable annuity rescue plan, and Social Security benefits when working vs. not working. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-317

Monthly Retirement Pension Vs. Lump Sum Payment: How to Choose -316 Mar 09, 2021

Choosing the pension lump sum or monthly payment: let it ride, roll it, or annuitize it? Plus, spitball analyses involving the 72(t) tax election, a donor-advised fund, 529 plans, and early retirement. Also, is growth on after-tax 401(k) contributions tax-free? How much of the portfolio should be in tax-free, taxable, and tax-deferred accounts? How does income from tax-deferred accounts impact Medicare premiums? Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-316

Are These Three Investment Products Too Good To Be True? - 315 Mar 02, 2021

Should you invest in a real estate investment trust (REIT)? What about a fixed indexed annuity or structured notes? What can be done about an indexed universal life insurance plan purchased by an employer to replace a defined benefit plan? Plus, understanding qualified small business stock gain exclusion. Joe and Big Al also discuss the value of hiring a CERTIFIED FINANCIAL PLANNER™. Are they worth it? Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-315

Is the Backdoor Roth IRA a Good Strategy For You? - 314 Feb 23, 2021

Are you eligible for a backdoor Roth IRA conversion? Is it taxed? How does a Roth 401k differ from a Roth IRA? Can you buy Mom's condo for below market value & rent it back to her? Can you max out Dad's Roth? Can you file 2020 taxes before receiving IRS form 1098? How should you diversify your portfolio into international investments? Plus, capital gains and ordinary income, and a correction on deemed Social Security. Access the transcript & financial resources, ask money questions: https://bit.ly/YMYW-314

Are You Financially Ready for Retirement? - 313 Feb 16, 2021

A retirement plan spitball analysis for an engineer wondering if he can afford to retire, required minimum distribution questions answered, and discussion on when to stop contributing to tax-deferred accounts, when to start Roth conversions, and a conversion strategy for someone with no income. Plus, "conversation" - not advice - about Joe's possible wallet syndrome, and a limerick and music from Paul Lemire. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-313

"Super Roth": Should You Overfund Supplemental Executive Retirement Plan Insurance? -312 Feb 09, 2021

Whether you call it a SERP, an individual supplemental executive retirement plan, a private pension, or the "Super Roth," the strategy is overfunding life insurance, and the question is, is it a good idea for retirement planning? Also: a Social Security, pension, retirement withdrawal, and Roth conversion strategy, portfolio modeling scenarios, the earned income tax credit, and other tax reduction strategies. Access the transcript and financial resources and ask your money questions: https://bit.ly/YMYW-312

Social Security, Medicare, HSA and Roth Conversions - 311 Feb 02, 2021

Find out just how intertwined healthcare and retirement are, with answers to questions about Medicare as it relates to Social Security, Health Savings Accounts (HSA), and IRA required minimum distributions (RMDs). Also, strategies for Roth conversions and Social Security, saving for retirement in a brokerage account, and paying debt out of retirement funds or with a mortgage refinance - and a couple of corrections. Access the transcript & financial resources, ask money questions: https://bit.ly/YMYW-311

[SPECIAL] GameStop: Stocks Gone Wild! Should You Join the Day Trading Craze? - 310a Jan 29, 2021

This week GameStop, AMC and Blackberry stocks went wild, with hedge funds shorting the stocks, and Redditors using the Robinhood investing app to put the squeeze on them - to the tune of billions of dollars. Is the stock market rigged? How do these investing plays affect you and your portfolio? Should you get in on the day-trading craze? Pure Financial Advisors' Executive Vice President and Director of Research Brian Perry, CFP®, CFA® joins Joe Anderson, CFP® to talk about it. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-310a

"The markets can remain irrational longer than you can remain solvent." - John Maynard Keynes, Economist

What's the Best Way to Take Retirement Distributions? - 310 Jan 26, 2021

Drilling down into the specifics of retirement distribution strategies: dollar cost averaging, pro-rata withdrawals, and buckets vs. the total return approach. Plus, a retirement withdrawal strategy with a side of pension and Social Security, another mortgage payoff question, the small business solo 401(k) trap, an LLC for a kayak side-hustle, and FIPhysician.com says nice things about YMYW. Access the podcast transcript and financial resources, and ask your money questions: https://bit.ly/YMYW-310

Retirement Plan Spitball Analyses for Side Hustles, Clergy & Grandkids - 309 Jan 19, 2021

Answering questions from across the personal finance spectrum: inherited IRAs and late RMDs, contributing to non-qualified deferred compensation plans, making Roth contributions for grandkids, how a Roth impacts student loans, taxation on ESPPs and RSUs, paying off the mortgage, and retirement plan spitball analysis for a clergyman and his wife, and for a couple with a profitable side hustle. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-309

How to Do the Mega Backdoor Roth IRA - 308 Jan 12, 2021

Backdoor Roth IRA withdrawal rules and the mechanics of the mega backdoor (dump truck!) Roth. Can you still contribute to a Roth after a rollover? How do you calculate Roth conversion taxes due to the pro-rata rule? Also, calculating a long retirement number or by age, a radical portfolio rebalance, why basis, gains, and losses are tracked, and donating stock upon death. Plus, does your financial advisor's location matter? Transcript, financial resources, ask your money questions: https://bit.ly/YMYW-308

How to Choose Your Pension Options and Retirement Withdrawal Strategy - 307 Jan 05, 2021

In this first YMYW episode of 2021, Joe and Big Al go over estate planning strategies for CFP® candidate/Redditor Nate in SC, they do a spitball analysis for John in TN who wants to retire early, a retirement withdrawal and 529 plan strategy for Ace in TX, and a breakdown of pension options for James in AZ - after Big Al figures out how to work his HP12C financial calculator. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-307

Social Security, Medicare and Real Estate - 306 Dec 29, 2020

Wrapping up the longest year in history with means testing for Social Security, healthcare when one spouse is on Medicare, and how Roth IRA conversions affect Social Security & Medicare costs. Plus, can you avoid capital gains when selling rental real estate? Should you pay off the mortgage on your rental property or keep investing? Is it a good idea to put a home equity line of credit (HELOC) on an investment property? Access the transcript, financial resources, ask money questions: https://bit.ly/YMYW-306

What's the Best Retirement Withdrawal Strategy? - 305 Dec 22, 2020

'Twas the Tuesday before Christmas and all through YMYW, Joe and Big Al's stockings were stuffed with your money questions: which strategy do they like best for retirement portfolio withdrawal? Plus, early retirement: calculating taxes correctly for it and dollar-cost averaging for it. Also, spreading SIPC risk, understanding the discrepancy in basis on a limited partnership, tax advantages of a health savings account (HSA), and some vehement listener comments on our discussion of paying off the mortgage from podcast #302. Access the transcript & financial resources, ask your money questions: https://bit.ly/YMYW-305

5 Last Minute Ways to Cut Your 2020 Taxes - 304 Dec 15, 2020

A final look at the CARES Act COVID-19 stimulus package, Coronavirus related distributions, and whether they affect your 2020 taxes. Plus, action items to pay less tax in 2020, like Roth conversions, tax gain and tax-loss harvesting, and charitable giving strategies. Also, when to do Roth contributions, how much of your portfolio should be in Roth accounts, and if you can lower your taxes from swing trading. Access the transcript & financial resources, ask your money questions: https://bit.ly/YMYW-304

How to Use Tax Diversification in Your Retirement Portfolio - 303 Dec 08, 2020

There are taxable, tax-deferred, and tax-free accounts, and the proper balance of investments in each is called tax diversification. Are you tax diversified enough? Plus, how do capital gains and ordinary income work again? Should you contribute to traditional 401(k) or IRA, or to Roth? What can you do about excess contributions to your Roth IRA? And to mix it up, are municipal bonds a good idea for conservative investors? Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-303

Should You Pay Off the Mortgage? First Consider Your Tax Strategy - 302 Dec 01, 2020

Paying off your mortgage? First, think of your investing and tax strategy. And, if you max out retirement and health savings accounts and own real estate, how else can you save? (Hint: brokerage account.) Should self-employed small business owners contribute to a Solo 401(k) or Traditional IRA? Solo Roth 401(k), or Solo 401(k) to Roth conversion? Finally, Medicare, HSA, capital gains, and modified adjusted gross income (MAGI). Access transcript, financial resources, and send in your money questions: https://bit.ly/YMYW-302

Borrow Money to Pay Tax on a Roth IRA Conversion? - 301 Nov 24, 2020

Should you borrow money to pay the tax on a Roth IRA conversion? Should you do a Roth conversion or capture non-qualified long term capital gains? How will Social Security benefits affect taxes after a backdoor Roth IRA conversion? Should a highly compensated employee use the mega backdoor Roth strategy? Are the tax savings on a conversion worth it? Plus the fellas explain the pro-rata rule - again. Access the episode transcript and financial resources, and send in your money questions: https://bit.ly/YMYW-301

Top Funniest Moments From the Your Money Your Wealth Podcast - 300 Nov 17, 2020

Joe and Big Al have been making retirement planning, investing, and tax reduction fun for years on the YMYW podcast. We're celebrating 300 episodes with just the funny stuff: great email intros, some of our funniest Derails, a couple never-before-heard outtakes, hilarious moments from our interviews with Dr. Daniel Crosby and Professor Jamie Hopkins, and the infamous story of Will and his free gasoline. Access the episode transcript and financial resources, and send in your money questions: https://bit.ly/YMYW-300

Rental Real Estate Property: How to Calculate Cap Rates and Depreciation - 299 Nov 10, 2020

When does the real estate depreciation 121 exclusion happen and how do you account for rental property equity, or cap rates, to calculate retirement income? Plus, estate planning beneficiaries and charitable donations, stock market investing in an LLC, understanding the national debt, the differences between Roth 40(k) and traditional 401(k), and of course, Backdoor Roth and Roth IRA conversions. Access the episode transcript and financial resources, and send in your money questions: https://bit.ly/YMYW-299

Retirement Portfolio Strategies and Making Sense of Fees - 298 Nov 03, 2020

Should retirement savings go in the older spouse's accounts first? Does Marion have a good VTSAX to VTWAX tax-loss harvesting and portfolio rebalancing strategy? Plus, making sense of fees from your financial advisor and on exchange-traded funds, or ETFs. Big Al provides pointers on selecting a good certified public accountant - other than him, of course, and finally, do 457 plans ever blow up? Access the episode transcript and financial resources and send in your money questions: https://bit.ly/YMYW-298

The Barn Door, Garage Door, Mega Backdoor Roth IRA Conversion - 297 Oct 27, 2020

What is the MEGA backdoor Roth IRA conversion and should you do one? How do you create retirement income for the gap between retiring at 66 and taking Social Security at 70 and RMDs at 72? Joe and Big Al also answer a question on the taxation of an overseas inheritance, and they discuss your comments. Access the episode transcript and financial resources and send in your money questions to be answered on the YMYW podcast: https://bit.ly/YMYW-297

YMYW Spitball Analysis 3: Tax Diversification and Asset Allocation - 296 Oct 20, 2020

On round 3 of the YMYW Retirement Plan Spitball Analysis, Joe and Big Al focus on your tax diversification and asset allocation questions: should more money be going into Christy's pre-tax Roth accounts? Has Roger set up a good portfolio for his elderly relative? Plus, the Rule of 100 or 120 for investing in stocks and bonds, as touted by Jack Bogle and the Bogleheads. Also, should Tom take a Coronavirus-Related Distribution? And finally, when to take Social Security, and that Social Security file and suspend rule that affects people born in 1954. Access the transcript and financial resources, send in money questions: https://bit.ly/YMYW-296

All About the Backdoor Roth IRA Strategy - 295 Oct 13, 2020

Should you wait until retirement to do a backdoor Roth IRA conversion? Plus, the pro-rata rule, self-employed modified adjusted gross income vs. AGI, and how capital gains work with Roth conversions. Also, strategizing for if and when the estate planning step up in basis tax laws change, whether a high yield savings account is good for investing $25K in cash, and listener comments on the show and the FIRE movement. Access transcript and financial resources, send in money questions: https://bit.ly/YMYW-295

Rebalancing Your Retirement Portfolio in Market Downturns - 294 Oct 06, 2020

Retirement portfolio rebalancing when the market goes down, accumulation, de-accumulation, dollar cost averaging, and IRR, ROR, and CAGR (not "kegger") as ways of calculating rates of return on investments. Plus step-up in basis, required minimum distributions or RMDs, capital accumulation life insurance plans, tax planning for new homebuyers, spousal Social Security benefits, and of course, backdoor Roth IRA conversions. Access transcript & financial resources, send in money questions: https://bit.ly/YMYW-294

Backdoor Roth Conversions and Investing for Kids - 293 Sep 29, 2020

Are you screwing up your Backdoor Roth IRA conversion? Find out. Plus, tax on mega-Backdoor Roth conversions, Medicaid spend-down rules and your Roth IRA, and Joe and Big Al take a burning confession about Roth conversions and IRS form 8606. Also, more on Vanguard's VTSAX and dividend yield, and various options for investing for minor kids including Paul Merriman's suggestions, UTMA, and brokerage accounts. Access transcript and financial resources, and send in money questions: https://bit.ly/YMYW-293

Will Estate Tax Law Changes Affect Your Family Financial Plan? - 292 Sep 22, 2020

How might Joe Biden's or Donald Trump's changes to the lifetime estate tax exemption impact your estate plan? Plus, is there any reason to have pre-tax retirement accounts? How long does money have to be in a traditional IRA before a backdoor Roth conversion? Can annuities be converted to Roth? And more on dividends, long term capital gains, Vanguard's Total Stock Market Index Fund, survivor Social Security benefits, and more. Access transcript and financial resources, send in money questions: https://bit.ly/YMYW-292

Roth Conversions, Annuities and Inherited IRAs - 291 Sep 15, 2020

Answering questions across the financial and retirement spectrum, with topics like when your traditional IRA is growing faster than you can convert to Roth, consolidating retirement savings, annuities, the SECURE Act and inherited IRAs, undoing SEP-IRA contributions, Roth conversions after age 72, offsetting conversion gains against tax-harvested losses, tax diversification beyond conversions, and what to do if you think you blew up your Roth IRA. Access the transcript, resources, send in money questions, and your chance at a $100 Amazon e-gift card in the show notes: https://bit.ly/YMYW-291

Market Timing and Day Trading in a Roth IRA? - 290 Sep 08, 2020

Is timing the market and day trading in your Roth IRA in retirement a good idea? How are you taxed if you collect dividends vs. reinvesting? Plus, tax loss harvesting, asset allocation, investing in bonds, the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) for spousal Social Security, and IRA vs. 529 plan for a newborn. Whew! Fill out the podcast survey for a chance to win a $100 Amazon e-gift card, send in money questions, and access free financial resources: https://bit.ly/YMYW-290

Backdoor Roth IRA Conversions, Stimulus and Self-Employed Retirement -289 Sep 01, 2020

How do you report a backdoor Roth IRA conversion over two tax years, and is there a point at which the backdoor Roth doesn't make sense? Plus, more strategizing for your Coronavirus related distribution, stimulus (and possible future stimulus) tax planning, and your self-employed, small business retirement plans. And finally, listener comments. Fill out the podcast survey for a chance to win a $100 Amazon e-gift card, send in money questions, and access the transcript and free financial resources: https://bit.ly/YMYW-289

YMYW Spitball Analysis 2: Retirement and Social Security - 288 Aug 25, 2020

The YMYW Retirement Plan Spitball Analysis was so popular that it's time for part 2! Where do Roth IRA conversions, primary residences, and rental real estate investment properties fit in your retirement plan? How much Social Security is taxed, and will taking your pension lump sum before Social Security impact your taxes? Fill out the podcast survey for a chance to win a $100 Amazon e-gift card, send in money questions, and access the transcript and free financial resources: https://bit.ly/YMYW-288

Roth Conversion Tax Planning Strategies and Annuities - 287 Aug 18, 2020

Tax planning for Roth IRA conversions with itemized deductions, dividends, and long term capital gains, a Roth conversion vs. investing a 401(k) distribution in your Roth, separating pre-tax and post-tax money for a rollover, and gong baths. Plus, is a 3 year fixed annuity a safe place to earn more than 20 basis points? What should you do if you're stuck in an annuity you don't want? Send in questions, access free financial resources, and sign up for the August 26 YMYW live webinar: https://bit.ly/YMYW-287

Dividend-Paying Stocks and Investing Strategies at All Ages - 286 Aug 11, 2020

Investing strategies for dividend-paying stocks and how the pro-rata rule for Roth conversions work with dividends. Plus, Wealthfront, M1, Paul Merriman? Should young investors use a robo-advisor or pay for financial advice? Also, thoughts on a Vanguard retirement portfolio and ideas for self-employed small business owners to save money in retirement plans like SEP IRA, SIMPLE IRA, and Solo 401(k). Send in money questions and access the episode transcript and free financial resources: https://bit.ly/YMYW-286

New Stimulus Check & Coronavirus Relief Package On the Way? - 285 Aug 04, 2020

With CARES Act provisions expiring, Joe & Big Al recap the two new stimulus bills - the HEALS Act and the HEROES Act - now being negotiated in Congress. Plus, estate planning considerations when it comes to required minimum distributions (RMDs) for non-designated and designated beneficiaries. And, the 403(b) escape hatch, Social Security, records of estimated tax payments, and assets on the FAFSA form. Send questions and access the transcript and free resources in the show notes: https://bit.ly/YMYW-285

What Is Your Retirement Number? YMYW Spitball Retirement Analysis - 284 Jul 28, 2020

Joe and Big Al spitball retirement plan considerations, including:

- investing in brokerage and Roth instead of pre-tax - getting tax diversification - pension lump sum or annuity - paying for education - calculating a retirement number to put savings on autopilot

Plus, what life insurance "investment" has a "guaranteed" 10% return? Do dividend paying stocks have a higher rate of return than VTSAX? Should individual stocks go in a taxable account?

Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/YMYW-284

Tax Gain Harvesting, Active vs. Passive Investments… and Roth Conversions - 283 Jul 21, 2020

Should you tax gain harvest or do a Roth IRA conversion? Should active or passive investments go in retirement accounts? If you're on the younger side, why own bonds? Are Vanguard Roth accounts any better or worse than others? What's the break even on taking Social Security early vs. late? Should you convert your 401(k) or retirement account to Roth all at once? Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/YMYW-283

How to Do a Roth Conversion and Pay Taxes On It - 282 Jul 14, 2020

Do you have to transfer from a 401(k) to a traditional IRA before you do a Roth IRA conversion? Does the pro-rata rule apply? Also, the logistics of paying the tax on a Roth conversion. Plus, stimulus package updates around paycheck protection program loans, required minimum distributions and Coronavirus-related distributions from retirement accounts. Send in money questions, access the episode transcript and free financial resources, and sign up for a free tax reduction analysis: https://bit.ly/YMYW-282

Will These Three Things Affect Your Social Security? - 281 Jul 07, 2020

What impact do ex-spouses, income, and early retirement have on collecting your Social Security benefits? Plus, indexed universal life insurance, estate planning with a step-up in basis on private placement real estate, and more on CRDs, RMDs, and stimulus checks. Joe and Big Al also submit their forecasts for whether Congress might tax Roth IRA growth in the future. Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/YMYW-281

Are These Retirement Investment Strategies On Track? - 280 Jun 30, 2020

Joe and Big Al take a look at an investing strategy a listener set up for his parents, and they run the numbers on their variable annuity. They also kick the tires on an early retirement plan and they discuss equity allocations in a portfolio. And since no YMYW is complete without some Roth talk, how might Roth contributions for grandkids affect college financial aid? Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/YMYW-280

Real Estate, Roth Conversions, and Social Security - 279 Jun 23, 2020

Reducing real estate taxes, leveraging new rental income properties, coordinating Social Security benefits with Roth conversions, and bragging about your 401(k) balance. Also, 5-year Roth clocks, converting from your TSP, Roth conversion vs. Backdoor Roth conversion, and paying taxes on conversions. Plus, a chat about Social Security survivor benefits - and freezers. Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/YMYW-279

Can You Do a Coronavirus-Related Distribution to Roth Conversion? - 278 Jun 16, 2020

Is it possible to do a Roth IRA conversion with a Coronavirus-Related Distribution from your retirement accounts? Joe and Big Al will explain whether you can, and if you should. Plus, more stimulus payment questions, charitable giving strategies from your required minimum distribution, selling stock for tax-free capital gains and an analysis of exchange traded funds vs. mutual funds. Send in money questions and access the transcript and free resources in the podcast show notes: https://bit.ly/YMYW-278

Roth IRA Conversion and Contribution Rules - 277 Jun 09, 2020

Roth IRA contributions and conversions come with plenty of rules: contribution rules, withdrawal rules, safe harbor rules, pro-rata and aggregation rules. In this episode, we explain these rules, and how they apply to both traditional retirement plans and accounts like SEP IRAs and thrift savings plans (TSP). Plus, understanding small-cap, mid-cap, large-cap, value, and growth asset classes when it comes to investing. Sign up for the exclusive YMYW live webinar on June 10, send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/YMYW-277

Pre-Tax or Roth Contributions for Retirement Savings? - 276 Jun 02, 2020

Should market volatility and the economic downturn due to COVID-19 change where you save for retirement? Should contributions go to pre-tax accounts or to post-tax Roth accounts? Plus, Coronavirus related distributions, how to use a PPP loan to pay your self-employed self, backdoor Roth IRA conversions, and strategies for funding a Roth IRA for children. Sign up for the exclusive YMYW live webinar on June 10, send money questions and access the transcript and free financial resources: https://bit.ly/YMYW-276

Social Security WEP, GPO & Roth IRA Conversion Strategies - 275 May 26, 2020

The windfall elimination provision (WEP), government pension offset (GPO) & spousal Social Security benefits. Also, Roth IRA conversions and Medicare, Roth conversions from a thrift savings plan (TSP), and conversions to buy real estate. Plus, asset location and other tax planning strategies beyond Roth IRA conversions, like life insurance and charitable remainder trusts. Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/YMYW-275

CARES Act: Distributions, RMDs & Dependents - 274 May 19, 2020

Financial planning strategies around Coronavirus-Related Distributions from retirement accounts and required minimum distributions (RMDs). Plus, listener corrections on dependents and the CARES Act stimulus package. Also, two very different market volatility strategies: living off of cash and Social Security only, and leveraging a home equity line of credit (HELOC) to invest. Sign up for the LIVE YMYW webinar on May 27, send in money questions, access the transcript and free financial resources: https://bit.ly/YMYW-274

Real Estate, Roth Conversions & Annuities - 273 May 12, 2020

A mixed bag of questions on everything from spousal solo 401(k) contributions and inherited IRAs to house-buying strategies, to the fan-favorite, ripping on annuities, with a healthy dose of Roth conversion planning thrown in the middle. Sign up for the LIVE YMYW webinar on May 13, send in money questions, read the episode transcript and access free financial resources: https://bit.ly/YMYW-273

Asset Location: Where Should You Hold Retirement Investments? - 272 May 05, 2020

What types of investments you keep in your taxable, tax-deferred and tax-free accounts can play a big part in how much tax you pay over time. In this episode, Joe and Big Al break down asset location and answer some of your tax planning questions. As always, the fellas also talk strategy when it comes to Roth IRA contributions and Roth conversions. Sign up for the LIVE YMYW webinar on May 13, send in money questions, read the episode transcript and access free financial resources: https://bit.ly/YMYW-272

4 Financial Strategies from the Stimulus Package - 271 Apr 28, 2020

In this jam-packed episode of the Your Money, Your Wealth® podcast, stimulus payments for self-employed, dependents, and those who message us on Facebook, plus, the paycheck protection program, round two of which started since this episode was recorded, coronavirus-related distributions, Roth and Backdoor Roth conversions, tax-loss harvesting, and the solo 401(k). Send in money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-271

In Market Volatility, Beware of Annuity Pitches - 270 Apr 21, 2020

In these volatile markets, pitches for fixed indexed annuities will be on the upswing. Here's how to analyze them for yourself. Plus, CARES Act stimulus payments for kids, retirement account distributions, and rethinking your retirement savings strategy. Also, SECURE Act stretch IRA rules, evaluating long term care insurance options, and why thrift savings plan (TSP) to Roth conversions are so complicated. Send in money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-270

Revisiting Roth IRA Conversion Strategies - 269 Apr 14, 2020

Roth IRA conversion pro-rata rule considerations with RMDs on an inherited IRA, tax bracket planning to account for the loss of a spouse, and the state income tax impact on Roth conversions. Plus, earnings on a reversed excess IRA contribution, how dollar-cost averaging affects capital gains tax first in, first out (FIFO) rules, zero-coupon bonds, whether to use the brokerage option in your 401(k) and more. Send in money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-269

CARES Act: What's in the Coronavirus Stimulus Package - 268 Apr 07, 2020

Recovery rebates, new rules for retirement account distributions, stimulus checks for those on Social Security & unemployment benefits. Plus, should a listener invest his forbearance, buy foreclosures, and capitalize on the financial crisis? We also get into the cash-on-cash math for rental real estate and potential property tax deduction changes for Californians under a revised Prop 13. Send in money questions, read the transcript & access free financial resources in the show notes: http://bit.ly/YMYW-268

Analyzing 5 Investing Strategies for Volatile Markets - 267 Mar 31, 2020

In these volatile financial markets, are you reconsidering your investing strategies? Joe and Big Al discuss cash, selling stocks in taxable accounts and repurchasing them in tax-deferred accounts, doing nothing and staying globally diversified, writing an investment policy statement, doing Roth conversions, and fixed indexed annuities (AKA equity-indexed annuities). Also: international and emerging market stocks, the Coronavirus stimulus package, inflation and much more. Send in money questions, read the transcript & access free financial resources in the show notes: http://bit.ly/YMYW-267

Tax Brackets Explained: How Much Are You Really Paying in Taxes? - 266 Mar 24, 2020

If you're in the 22% tax bracket, does 22% of what you make go to the IRS? How does capital gains tax work with ordinary income tax? Joe & Big Al explain how tax brackets work and answer your Roth contribution and Roth conversion questions: like what's the point of a Roth conversion if you're just leaving the money to your kids? Plus some Mega Backdoor Roth talk and spousal contributions. Send in money questions, read the transcript & access free financial resources in the show notes: http://bit.ly/YMYW-265

Bear Market Investing Strategies and Revisiting the 5-Year Roth IRA Withdrawal Rules - 265 Mar 17, 2020

Tax loss harvesting, Roth conversions and more: Joe and Big Al explain how bear markets like the one we're in now are the time to utilize these investing strategies in your retirement portfolio. And the fellas go over those Roth IRA 5-year withdrawal rules again. They'll cover some Roth withdrawal mistakes and Roth rollover consequences, and they have a mea culpa for one of their peers. Send in money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-265

How Much of Your Net Worth Should Be in Cash? - 264 Mar 10, 2020

How much of your money should you keep in cash? Should you buy VBK, the Vanguard Small-Cap Growth ETF? Plus, asset allocation and asset location, the pros and cons of the Roth 401(k), Medicare, spousal and survivor Social Security benefits, tax-saving charitable giving, small business strategies, who qualifies to be called Joe Anderson's "peer," and whether you'd rather hang out with a James or a Jimbo. Send in money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-264

7 Roth Conversion Strategies - 263 Mar 03, 2020

When to do a Roth IRA conversion, the pro-rata and aggregation rules, spousal conversions, Roth contributions and more. Send in money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-263

What's the Right Retirement Asset Allocation for You? - 262 Feb 25, 2020

With volatility, should you time the market and change the asset allocation of your investment portfolio, your pension, or your Thrift Savings Plan (TSP)? Plus, asset location: should equities be in a brokerage account, Roth IRA or traditional IRA? And diversification vs. concentration, calculating how much you'll have in retirement, how to get there from here, and Joe's favorite, negative listener feedback. Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-262

Real Estate Investing: How to Find Bread & Butter Rental Properties - 261 Feb 18, 2020

How do you run the numbers to find a good, profitable rental property? Should you pay off the mortgage, buy more real estate, or save for retirement? Should you buy a home all cash? Can a property be considered a rental for tax purposes? Should you refinance your home to pay student loans? What can you do with unused education savings? And what do we have against 72(t) SEPP for early retirement withdrawals? Ask money questions, read the transcript and access free financial resources: http://bit.ly/YMYW-261

When is the Tax Deadline for a Roth Conversion? - 260 Feb 11, 2020

As Tax Day approaches, you've got taxes on your mind. When do you have to pay the tax on your Roth IRA conversion? Is converting beyond the current tax bracket ever recommended? Plus, answers to more of your SECURE Act retirement questions on IRA contributions and inherited IRAs and other assets, and Roth conversion and Backdoor Roth strategies for self-employed small business owners with Solo 401(k)s and SIMPLE-IRAs. Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-260

"Collect Social Security at Age 70" is Common Advice. Why? - 259 Feb 04, 2020

We address a challenge to the advice to wait until age 70 to take Social Security and we tackle your questions on making the most of your benefits, what happened to annual projections for those on restricted applications, using a revocable trust to protect assets from Medicaid, converting from 403(b) to Roth IRA, rolling Roth 401(k) to Roth IRA, and whether to contribute to a Roth 401(k) or Traditional 401(k). Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-259

International Funds, Safe Investments, 1031 Exchange: Email Round-Up - 258 Jan 28, 2020

How to choose international funds in a diversified portfolio, a momentum investing strategy called The 12% Solution, and safe retirement investments like CDs and bonds. Plus Joe and Big Al touch on real estate investing with 1031 exchanges and qualified opportunity zones, and they answer your questions on the SECURE Act, IRA contributions, and calculating Social Security in this wide-ranging email round-up. Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-258

Why Not Just Go All in On VTSAX, Vanguard's Total Stock Market Index Fund? - 257 Jan 21, 2020

The Vanguard Total Stock Market Index Fund (VTSAX) comes very highly recommended by JL Collins in his book, The Simple Path to Wealth. So why not put all your money into it? Plus, Joe & Big Al answer your questions on the 4% rule for retirement withdrawals, what to do before and after age 59 and a half, whether to invest in the Roth or traditional thrift savings plan (TSP), and of course, Roth IRA conversions. Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-257

Your SECURE Act Retirement Questions Answered - 256 Jan 14, 2020

Joe and Big Al tackle your SECURE Act retirement planning questions: how minors can distribute inherited IRAs, whether a trust should be your IRA beneficiary, and what effect the new law has on required minimum distributions, or RMDs, and qualified charitable distributions, or QCDs. Plus, the fellas get schooled by YMYW listeners on their Thrift Savings Plan miss in episode 254. Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-256

Breaking Down the Confusing 5-Year Roth Clock Rules - 255 Jan 07, 2020

Joe & Big Al explain, once and for all, the 5-year clocks for Roth conversions and Roth contributions and pro-rata rules. (Well, hopefully it'll all make more sense to you by the time they get through it. If not, let us know.) We'll also find out what the fellas think about holding cash until the inevitable economic downturn, lump-sum investing versus dollar-cost averaging, and the Total World Stock Index Fund. Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-255

Roth Conversions from a Thrift Savings Plan TSP? - 254 Dec 31, 2019

The thrift savings plan (TSP) explained, and the rules around Roth conversions from TSPs. Plus, Joe and Big Al answer your questions about, what else, Roth conversions and contributions: age limits on making conversions, backdoor Roth conversions, Roth contribution phase-outs and recharacterizations, and the pro-rata rules. Plus, Joe explains, again, his distaste for fixed index annuities, and we find out why Big Al is called "Big". Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-254

Rules for Your Retirement Savings and Distributions Are Changing - 253 Dec 24, 2019

Just in time for the holidays, the Setting Every Community Up for Retirement Enhancement Act, or SECURE Act, has been made law, effective January 1, 2020. Joe and Big Al explain what it means for your stretch IRAs, required minimum distributions, retirement savings and more. Plus the fellas answer your questions on self-employed small business retirement plans and paying off the mortgage. Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-253

Strategies for Social Security, Annuities, and Inherited Assets - 252 Dec 17, 2019

Joe and Big Al answer questions about coordinating Social Security benefits with Roth contributions and required minimum distributions, weighing the Social Security restricted application against survivor benefits, the Windfall Elimination provision for teachers, whether to take RMDs from a brokerage IRA or an annuity - and of course, Joe will explain why that annuity is a terrible idea - and the fellas get into how to split an inherited annuity four ways and how to split a house eight ways! Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-252

Should You Convert to Roth IRA All at Once or Over Time? - 251 Dec 10, 2019

How much of a Roth conversion should you do and when? Does it make sense to convert to a Roth IRA all in one year, or to do it over time, based on your age? Joe and Big Al explain the reasoning behind their answer to this common retirement investing question. Plus, they answer your questions about converting from a thrift savings plan (TSP) to a Roth, limits when contributing to retirement accounts and a traditional IRA, and doing the tax math to decide if a Roth conversion is right for you. Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-251

Tanja Hester on the Flexibility of Financial Independence - 250 Dec 03, 2019

Tanja Hester (called the Matriarch of the women's FIRE movement by the New York Times) returns to YMYW to discuss the value of our time, how it's connected to our money, and the options financial independence provides for a life well-lived. Plus, Joe and Big Al answer questions about the balanced asset allocation strategy, taking a pension and another job AND Social Security, and what to do when your company changes 401(k) custodians. Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-250

What's the Break-Even on a Retirement Roth IRA Conversion? - 249 Nov 26, 2019

How do you figure out the break-even point on a Roth IRA conversion? Joe and Big Al discuss whether to convert, how much to convert, and when. Plus, the step-up in basis on a primary residence, self-employed small business retirement plan options, the difference between a financial advisor and financial planner, and defining a registered investment advisor and broker-dealer. Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-249

Is a Roth Conversion Affected By Social Security? - 248 Nov 19, 2019

Will a Roth IRA conversion be impacted by your Social Security benefit or vice versa? Plus, today we're talking Social Security spousal and survivor benefits, Roth IRA conversions, earned income, ordinary income, modified adjusted gross income, and taxable income. We're also talking about taking this job, shoving it, and doing Roth conversions all the way to Tennessee! Ask money questions, read the transcript & access free financial resources: http://bit.ly/YMYW-248

How to Talk to Mom & Dad About Their Money - 247 Nov 12, 2019

Cameron Huddleston discusses her book, Mom and Dad, We Need to Talk: How to Have Essential Conversations With Your Parents About Their Finances. But first, let's get into glide path: should you invest more aggressively through retirement? Which assets should you spend before you take Social Security? What should your portfolio withdrawal strategy be if you don't plan to retire? And when asked how to pay taxes on a Roth conversion, Joe and Big Al make a suggestion rarely heard on YMYW (hint, it involves debt and your primary residence). Ask your money questions, read the transcript, and access free financial resources at http://bit.ly/YMYW-247

Why This Life Insurance Is for the Most Part a Scam - 246 Nov 05, 2019

We tackle Indexed Universal Life Insurance one more time. And you may have heard that millionaires "buy term and invest the rest" to pay estate taxes, but is it a good idea? When you have appreciated company stock, how much should you "NUA" and when, and how do you deal with the taxes? Plus, can you convert an inherited 401(k) to a Roth? When is your required beginning date for RMDs? Ask your money questions, read the transcript, and access free financial resources at http://bit.ly/YMYW-246

Is It Time to Fire Your Financial Advisor? - 245 Oct 29, 2019

Should you stay or should you go? Joe and Big Al weigh in on whether a couple of listeners who are dissatisfied with their financial advisors should ditch or keep the advisors. Plus, how should you choose investments in your 401(k)? Is it a good idea to make Roth contributions for your kids? How do you manage taxes and penalties because of Roth conversions? Ask your money questions, read the transcript, and access more free financial resources at http://bit.ly/YMYW-245

5 Unique Social Security Questions Answered - 244 Oct 22, 2019

Social Security strategies if you are married to a younger spouse and have a minor child, affected by the windfall elimination provision, considering divorce for a better benefit, or unsure of the restricted application. And should you spend 401(k) money before taking Social Security? Next up, real estate: should you gift property now to reduce taxes later? Should you pay off your home? And the section 121 exclusion of gain from the sale of a principal residence on a split property. Transcript, show notes, and free financial resources: http://bit.ly/YMYW-244

The Truth About Indexed Universal Life Insurance - 243 Oct 15, 2019

Is indexed universal life insurance good for estate planning, investing or as a tax shelter for high-income earners? Should you pay down debt or save if you only have $100K saved for retirement at age 66? Should extra money be invested in your 457 or brokerage account? ETFs or mutual funds? And with the new tax laws scheduled to sunset in 2026, does it make sense to do a giant Roth conversion in 2025? Transcript, free resources, and show notes: http://bit.ly/YMYW-243

Investing the Money from a Real Estate Sale - 242 Oct 08, 2019

You've sold your primary residence or your rental property. How should you invest real estate proceeds for retirement? When do Joe and Big Al say you shouldn't do a Roth conversion? What's the math on federal vs state taxes when doing a Roth conversion if you move to a no income tax state? And how is your pension taxed if you move? Transcript, free resources, and show notes at http://bit.ly/YMYW-242

Answers to Your Top Roth Conversion Questions - 241 Oct 01, 2019

Your Roth IRA questions answered: when should you do a Roth conversion? Should you wait until you're in retirement to convert? What kind of income is it? How do you convert slowly so the tax bite doesn't hurt so much? How long do you have to work before you can contribute to a Roth IRA? Does the 5-year rule apply for Roth withdrawals after age 59 1/2? Plus, answers to non-Roth money questions about estate planning, reverse mortgages, transferring from a variable annuity to a traditional IRA, and using HSA funds to pay Medicare premiums. Transcript, free resources, and show notes at http://bit.ly/YMYW-241

How to Choose Your Own Financial Independence Adventure - 240 Sep 24, 2019

Choose FI: Your Blueprint to Financial Independence authors Chris Mamula (CanIRetireYet.com), Brad Barrett and Jonathan Mendonsa (Choose FI podcast) share principles that can change your life and your idea of retirement. Plus, answers to your FIRE (financial independence / retire early) questions on bridging the gap between early retirement and tapping retirement accounts, balancing ACA subsidy eligibility against allocation decisions, options trading, and just how much Roth savings is right for you. Transcript & show notes: http://bit.ly/YMYW-240

How Should You Invest? As Always, It Depends - 239 Sep 17, 2019

This week's questions all revolve around what to do with your money - and everyone's circumstances are different. What to do with a 401(k) after you retire and don't really need the money just yet? What to do with cash in savings? Is the Papa Bear portfolio a good one? How best to save for retirement when you're a sole proprietor AND a teacher? How to handle the basis in an s-corporation you're closing down? Transcript, free financial resources, and show notes: http://bit.ly/YMYW-239

Roth Conversions, Life Insurance & More: Email Round-Up - 238 Sep 10, 2019

An entire episode dedicated to money questions that run the gamut: we're talking about using indexed universal life insurance to insure future income, buying mutual funds or ETFs in an IRA, Roth contributions and conversions, changes to the thrift savings plan, doing a reverse mortgage leading into a possible recession, the Mega-Backdoor Roth strategy, what happens to retirement accounts in a divorce and more. Transcript, free financial resources, and show notes: http://bit.ly/YMYW-238

Mad at the Roller Coaster? Then You Don't Understand the Ride - 237 Sep 03, 2019

Back to investing basics: what makes for a wise investing philosophy while on the market volatility roller coaster? How do you find a financial fiduciary? How do you avoid people with bad financial intentions? What is a good investment policy statement? How do you figure out the annual percentage rate on an IRS payment plan? When should a teacher retire, and what should she do with her pension? Plus some Roth conversion talk, as you'd expect. Transcript & show notes: http://bit.ly/YMYW-237

How Much Can You Spend When You're On FIRE? - 236 Aug 27, 2019

What's a safe withdrawal rate from your investment portfolio when that money has to last 50 or 60 years because you're part of the FIRE (financial independence/retire early) movement? Karsten Jeske, Ph.D., CFA, aka "Big Ern" from EarlyRetirementNow.com shares his experiences. Plus, will listener Paul reach $5M by retirement? Can monthly payments from an IRA annuity be used for qualified charitable distributions (QCDs)? And what happens if you've made mistakes with your IRA that lead to penalties? Transcript, resources & show notes: http://bit.ly/YMYW-236

Recession and the Inverted Yield Curve - 235 Aug 20, 2019

An inverted yield curve has often led to a recession. Pure Financial Advisors' Executive Vice President and Director of Research, Brian Perry, CFP®, CFA, discusses the current state of the markets and he helps answer some questions from our 2019 YMYW podcast survey: are structured notes ever a good product? How can you make the most of small retirement contributions? How do you grow a portfolio, when should you rebalance, how should you invest, and what's a safe withdrawal rate? Transcript, resources & show notes: http://bit.ly/YMYW-235

Tax Postcard, Stretch IRAs & Life Insurance for Education - 234 Aug 13, 2019

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The revamped 2019 tax "postcard," how the SECURE Act could be a tax problem for those with IRA trusts, and is indexed universal life insurance a good investment for education costs? Should you roll your 401(k) to an IRA? How much can you convert from 401(k) to Roth after age 70 and a half? Will you go to jail for filing your taxes before receiving form 5498? Transcript, free financial resources, and show notes: http://bit.ly/YMYW-234

Using Alternative Investments to Boost Portfolio Returns? - 233 Aug 06, 2019

Private equity, venture capital, hedge funds, real estate investment trusts (REITs) and angel investing: Joe breaks down what these alternative investments are and whether they belong in your portfolio. Plus, the fellas talk about risk parity investing, net unrealized appreciation, what to do with a large settlement and the break-even point for Social Security benefits. Transcript, free financial resources & show notes: http://bit.ly/YMYW-233

Time to Dial Down Risk and Do a Roth Conversion? - 232 Jul 30, 2019

Jonathan Clements (founder, HumbleDollar.com, former Wall Street Journal personal finance writer) on portfolio rebalancing, reducing risk and doing a Roth conversion. Plus, Joe and Big Al answer your money questions: when is the best time to get into the market? When is the best time to retire? Can you start a Roth IRA for your Dad? And should you roll your 401(k) into a traditional or Roth IRA? Finally, some YMYW compliments and complaints. Transcript & show notes: http://bit.ly/YMYW-232

Appreciate How Good the Economy is Now - 231 Jul 23, 2019

According to Dr. Chris Thornberg of Beacon Economics, the US economy and real estate market are currently extremely healthy, so we should appreciate it and focus now on fixing the retirement crisis we're facing in 10-15 years. Plus, Joe and Big Al answer your money questions: Why is owning a home considered "profitable"? Is it a good idea to own real estate in a self-directed IRA? And should you buy a fixed index annuity? Transcript & show notes: http://bit.ly/YMYW-231

The Effect of the Media on Financial Markets - 230 Jul 16, 2019

Does the media impact financial markets and the economy? Oliver Renick (TD Ameritrade Network) has ideas on how we can best make use of what the media tells us about the financial world. Plus, where should bonds be allocated to lessen the tax burden? Should you contribute to a Roth 401(k) or traditional 401(k)? And a call from a listener with a strong opinion on the FIRE movement (financial independence/retire early). Transcript & show notes: https://link.chtbl.com/ymyw-230

Strategies for Social Security, Gifting, and Estimated Taxes - 229 Jul 09, 2019

Joe Anderson, CFP® and Big Al Clopine, CPA answer your questions on Social Security disability, the file and suspend strategy, IRA contributions and Roth conversions, estimated tax, estate tax, gift tax, Social Security tax, the qualified business income deduction, selling appreciated stock, and whatever else they can jam in. Transcript & show notes: http://bit.ly/YMYW-229

Liz Ann Sonders: Investing in the Face of Recession - 228 Jul 02, 2019

"If we're heading to a recession, we're already in it." Liz Ann Sonders (Chief Investment Strategist, Charles Schwab & Co.) shares her mid-year market insights and provides strategies for removing the emotion from investing, regardless of market conditions. Plus, Joe and Big Al answer your money questions: how do you diversify a portfolio for the best returns and tax efficiency? And when does it make sense to do a traditional 401(k) instead of a Roth 401(k)? Transcript & show notes: http://bit.ly/YMYW-228

This Retiree Helps Golfers Reach the Big Time - 227 Jun 25, 2019

Rick Durso tells us what his retirement hustle is like as a caddy for the Symetra golf tour, helping golfers make it to the Ladies Professional Golf Association (LPGA). Plus, Joe and Big Al answer your money questions about Roth conversions, solo 401(k) plans for the self-employed, and they get taken to task for something they said in last week's episode on Medicare. Transcript & show notes: http://bit.ly/YMYW-227

Medicare Beginner's Guide: What You Need to Know Now - 226 Jun 18, 2019

Danielle Kunkle Roberts of BoomerBenefits.com on Medicare basics, parts A to D, signing up, common mistakes, Medigap vs. Medicare Advantage, recent improvements to Medicare, and the future: will Medicare For All or Medicare At 50 become reality? Plus, Joe and Big Al answer your money questions: are health insurance premiums deductible? And when do you pay taxes to the IRS when you plan your charitable donations over multiple years? Transcript and show notes: http://bit.ly/YMYW-226

Real Estate Investing: Should You Buy Raw Land? - 225 Jun 11, 2019

The Land Geek Mark Podolsky shares his method for turning unwanted dirt and "rock farms" (aka raw land) into cash. Plus, can you aggregate rental properties into an LLC to take advantage of the qualified business income deduction? And can you avoid state taxation on your required minimum distributions (RMDs) if you move to a state that doesn't tax retirement accounts? Transcript & show notes: http://bit.ly/YMYW-225

New Retirement Legislation: Death to the Stretch IRA? - 224 Jun 04, 2019

Professor Jamie Hopkins (Carson Wealth & Heider School of Business/Creighton University) talks about impacts the SECURE Act could have on retirement planning - particularly the end of the stretch IRA provision, which allows inherited individual retirement accounts to remain tax-deferred. Plus, how to reduce taxes when you have significant capital gains, when you can take tax-free and penalty-free 457 distributions, and whether or not to max out your 401(k). Transcript & show notes: http://bit.ly/YMYW-224

Financial Independence Retire Early Hits the Big Screen - 223 May 29, 2019

Travis Shakespeare, Director and Executive Producer of Playing with FIRE, talks about making the first-ever documentary about the Financial Independence / Retire Early or FIRE movement. Plus, Joe and Big Al answer your rental real estate investing questions and clear up some confusion around Roth 401(k) income limits and contributions vs. conversions. Transcript and show notes: http://bit.ly/YMYW-223

How to Be Like the Millionaire Next Door - 222 May 21, 2019

Dr. Sarah Stanley Fallaw (co-author, The Next Millionaire Next Door) shares her research into how millionaires become wealthy, and what has changed since her father, Thomas J. Stanley, wrote his groundbreaking book The Millionaire Next Door in 1996. Plus, what should you do with universal life insurance policies with large cash values? Will you pay income tax on a Roth conversion made after you move from California to a no-income-tax state like Texas? Transcript & show notes: http://bit.ly/YMYW-222

How to Hedge Risk From the Brothel to the Surfboard - 221 May 14, 2019

Economist Dr. Allison Schrager, the author of An Economist Walks Into a Brothel, explains how the risk management techniques of surfers, prostitutes, magicians, and soldiers might relate to our own investing and retirement planning. Plus, stocks or bonds - does it matter which assets you withdraw first from your retirement portfolio? And how much can you convert to a Roth IRA without incurring the 3.8% Medicare surcharge? Transcript & show notes: http://bit.ly/YMYW-221

Social Security, TSP Changes, & Maintaining Your Tax Bracket - 220 May 07, 2019

Joe & Big Al answer your questions: from filed-and-suspended Social Security, living off of your investments overseas before taking Social Security, and transitioning from disability to regular Social Security, to how the sale of appreciated company stock or a Roth conversion will change your tax bracket, and what you need to do to prove a change to your state of residency. Plus, the fellas explain how the pro-rata rules for Thrift Savings Plans have changed. Transcript & show notes: http://bit.ly/YMYW-220

Standup Comedy: Gid Pool's Retirement Hustle - 219 Apr 30, 2019

Gid Pool took a standup comedy class 13 years ago at age 61 on a lark. He shares the story of his retirement hustle, traveling the US and 50+ countries as a standup comic, inspirational speaker, and the author of Act II and Beyond: Making the Rest of Your Life Spectacular. Plus, Joe and Big Al follow-up on ERISA protection for SEP IRAs, they discuss the Qualified Business Income Deduction for owners of rental real estate, and they offer financial tips and investing ideas for high school grads and college students. Transcript & show notes: http://bit.ly/YMYW-219

3 Ways to Turn Your Financial Negatives Into Positives - 218 Apr 23, 2019

Kristin Wong (author, Get Money, columnist, Joint Accounts @ Medium.com) talks about relationships and money and how communication, specificity, and gamification can improve your financial life. Joe and Big Al answer your money questions: should you increase your Roth 457 contribution when your spouse wants to retire 8 years before you? Does a SEP IRA have the same protections as a 401(k)? Must a company allow third-party management of a 401(k)? Plus, Big Al admits he answered a question incorrectly last week. Transcript & show notes: http://bit.ly/YMYW-218

How to Use Rental Real Estate to Build Legacy Wealth - 217 Apr 16, 2019

Top apartment broker Terry Moore, CCIM talks about using rental real estate not just to build wealth, but also to create a life worth imitating. Joe and Big Al answer your questions: can excess scholarship money be contributed to a Roth IRA? Will stock and bond income affect Social Security benefits? The fellas also do a couple of retirement assessments on the fly to help listeners generate and maximize retirement income while minimizing taxes. Transcript & show notes: http://bit.ly/YMYW-217

Here's What to Do When You're a Victim of Debit Card Fraud - 216 Apr 09, 2019

Ashley Patrick (former police detective and creator of BudgetsMadeEasy.com) on how debit card fraud happens, what to do when your ATM card is compromised, and ways to avoid it happening in the future. Plus, Joe & Big Al answer your money questions: how do you determine a good pre-tax to Roth savings ratio? Are trading apps and online trading services a good idea? Can you "retire," take money from your retirement plan, then return to work for the same company? And the age-old pension question: should you take the lump sum or the monthly annuity payment? Transcript & show notes: http://bit.ly/YMYW-216

Will Trump's Latest Proposals Reduce Student Loan Debt? - 215 Apr 02, 2019

David Carlson (author, Student Loan Solution) discusses the student loan debt crisis and President Donald Trump's plan to fix it, and Joe and Big Al answer listeners questions about contributing to a retirement plan without an employer match, doing in-plan Roth conversions, changing retirement accounts to protect investment properties and more. Transcript and show notes: http://bit.ly/YMYW-215

The Real Keys to Being Rich and Truly Wealthy - 214 Mar 26, 2019

Brian Portnoy, Ph.D., CFA® (author, The Geometry of Wealth) on the difference between being rich and wealthy, and how to achieve both. Plus, what about tax brackets? Joe and Big Al respond to a challenge of their critique of Ric Edelman's critique of the Roth IRA. And they answer questions that stress the importance of understanding financial vocabulary in retirement planning: Roth contributions vs. conversions, the Roth 5-year clock, and the difference between transfers and rollovers. Transcript & show notes: http://bit.ly/YMYW-214

Social Security Changes in 2019 - 213 Mar 19, 2019

Joe and Big Al discuss 7 changes to your Social Security for 2019. No, wait, six changes. Well actually, it's more like 5 changes and a useful tidbit. Plus, when to claim your spousal benefit, whether to buy long-term care insurance or self-insure, how to get more growth in your portfolio without adding more risk, and where to keep your emergency funds. Transcript and show notes: http://bit.ly/YMYW-213

Problems With the Arguments Against Roth IRAs - 212 Mar 12, 2019

Ric Edelman has some strong arguments against the Roth IRA. Joe & Big Al, aka "The Roth Brothers," offer their thoughts. Plus, understanding basis when it comes to Roth conversions. And what happens if you've already contributed, but by the end of the year you've exceeded the income limitation for Roth contributions? Can you open a Roth for your 12-year-old whose raking in babysitting bucks? What happens to your Roth when you die? It's an all Roth IRA episode! Transcript & show notes: http://bit.ly/YMYW-212

Retire Early Without Pinching Pennies - 211 Mar 05, 2019

Tanja Hester (OurNextLife.com, award-winning financial independence blog) talks about her new book, Work Optional: Retire Early the Non-Penny-Pinching Way. Joe and Big Al answer questions about whether kids will inherit a Roth IRA tax-free, the rules around a traditional IRA rollover, investing in a Vanguard target date fund, and where to safely invest for growth. Transcript and show notes: http://bit.ly/YMYW-211

"Hold It" Until You're Purple to be a Better Investor - 210 Feb 26, 2019

Behavioral finance expert Dr. Daniel Crosby talks about his latest book, The Behavioral Investor and cracks us up with stories of how "having to go" and other physiological, sociological, and psychological factors influence our investing choices. Plus, Joe and Big Al answer money questions about ACA subsidies and Roth conversions, strategies for reducing the tax burden on 1099 income to zero, and donating a required minimum distribution to multiple charities. Transcript and show notes: http://bit.ly/YMYW-210

Are These Two Funds the Only Ones You Need for Life? - 209 Feb 19, 2019

Nationally recognized investing expert Paul Merriman makes the case that owning just two funds for life is a "home-run" investing strategy for some investors. Plus, Joe and Big Al answer your money questions: how should teachers, and others without Social Security or pension, save for retirement? How do you record flexible spending account contributions on your taxes? How long should you keep your tax records? And of course, this wouldn't be YMYW without some talk about Roth IRAs - specifically, making Roth conversions and back door Roth contributions. Transcript & show notes: http://bit.ly/YMYW-209

Spousal Social Security Claiming Strategies You Need to Know - 208 Feb 12, 2019

Did you know there are over 2,700 rules governing Social Security benefits? File and suspend vs restricted claim... the list goes on! Mary Beth Franklin (InvestmentNews contributing editor, "The Goddess of Social Security") goes deep on spousal Social Security claiming strategies after Joe, Big Al and Andi tackle a couple Social Security disability and spousal benefits questions on their own. Mary Beth caps also explains the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO). Transcript & show notes: http://bit.ly/YMYW-208

This Myth is the #1 Barrier to Financial Freedom - 207 Feb 05, 2019

Grant Sabatier (author, Financial Freedom) share some of the steps that led him from $2.26 in the bank to over a million bucks in just 5 years, and the myth that he believes is the #1 barrier keeping the rest of us from achieving the same thing. Plus, a conversation about Senator Elizabeth Warren's wealth tax proposal, Joe and Big Al answer a question about keeping taxes in mind as part of an investing strategy, and a look at the complete disaster that was the Fyre Festival. Transcript and show notes: http://bit.ly/YMYW-207

How to Avoid the Five Horsemen of the Retirement Apocalypse - 206 Jan 29, 2019

Larry Swedroe (Buckingham Strategic Wealth) talks about his 16th book, Your Complete Guide to a Successful and Secure Retirement, the two biggest retirement mistakes, and what Larry calls the five horsemen of the retirement apocalypse. Plus, is there a way to consolidate your investment portfolio before you retire and avoid paying capital gains tax? Also, dancing to stave off dementia, the world of golf, and China and Brexit news - but probably not what you're expecting. Transcript and show notes: http://bit.ly/YMYW-206

5 Key Attributes That Make Millionaires Successful - 205 Jan 23, 2019

Chris Hogan of Ramsey Solutions talks about his brand new book, Everyday Millionaires: How Ordinary People Built Extraordinary Wealth – and How You Can Too. Joe and Big Al answer your money questions: do the stretch IRA rules apply to 401(k)s? Do you need to get an annual property appraisal if you own real estate in a self-directed IRA? And what is the best strategy for saving into retirement accounts and making Roth IRA conversions? Plus, a tribute to Jack Bogle of Vanguard, and a look at states' efforts to develop financially literate high school students. Transcript and show notes: http://bit.ly/YMYW-205

Liz Ann Sonders: Recession Inevitable, the Question is When? - 204 Jan 15, 2019

Liz Ann Sonders (Chief Investment Strategist, Charles Schwab & Co.) provides insight on what happened in the market in 2018 and her outlook for 2019. Liz Ann discusses the causes of recent market volatility, the Fed funds rate, the possibility of a recession in 2019 and what investors should do now. Plus, Joe and Big Al answer your email questions: If you're saving 55% of your income, should you keep saving or have more fun? Should you save for kids' college or your own retirement? Isn't deciding when to take Social Security a lifestyle choice? Finally, a look at how the gurus fared with their 2018 market predictions. Transcript & show notes: http://bit.ly/YMYW-204

Sex and Immigration: How Do They Affect Social Security? - 203 Jan 08, 2019

Devin Carroll (Big Picture Retirement podcast, Social Security Intelligence blog) explains how sex could save Social Security and the surprising effect that immigration has on your benefits. Joe and Big Al answer your money questions: How should I diversify from a single highly appreciated asset? They discuss charitable remainder trusts, life insurance trusts, and the collar strategy. Plus, one of the most common questions: will I outlive my money in retirement? Transcript and show notes: http://bit.ly/YMYW-203

4 Simple Ways to Keep Your New Year's Resolutions - 202 Jan 01, 2019

Marcus Garrett from Paychecks and Balances and author of Debt Free or Die Trying: How I Buried Myself in Over $30,000 in Debt and Dug My Way Out by Age 30 tells us the four simple actions he takes to make his New Years resolutions stick. Plus, Joe and Big Al answer your money questions: Do I owe taxes on a property gifted to me? Why would I use a financial advisor? And what are the small business owner limits on Roth and 401(k) contributions? Happy New Year from Your Money, Your Wealth®! Transcript and show notes: http://bit.ly/YMYW-202

7 Benefits of the Federal Reserve Interest Rate Hikes - 201 Dec 26, 2018

What do the increases in the Federal Reserve interest rates mean for the economy and our portfolios - and how can we benefit from the rate hikes? Lindsey Stanberry dishes about Refinery29 Money Diaries. Joe and Big Al answer your money questions on state vs. federal tax deductions, saving for retirement vs. paying debt, and RMDs on an inherited non-spouse Roth IRA. Plus, why did Joe say indexed annuities are some of the worst investments on the planet? Transcript & show notes: http://bit.ly/YMYW-201

How to Avoid the Top 8 Holiday Scams of 2018 - 200 Dec 18, 2018

Julia Wang from ValuePenguin.com tells us which holiday scams are all the rage this season - and how to be smarter than the scammers. Joe and Al answer questions about Roth conversions, Medicare premiums, RMDs, and taxes, doing a 1031 exchange for rental real estate when you don't really want the property, and what your financial bucket list should include before you retire. Transcript and show notes: http://bit.ly/YMYW-200

How to Use Leverage to Reduce Risk and Increase Returns - 199 Dec 11, 2018

Todd Tresidder of FinancialMentor.com shares the surprising ways to reduce risk and increase returns as outlined in his new book, The Leverage Equation: How to Work Less, Make More, and Cut 30 Years off Your Retirement Plan. Joe and Big Al answer your money questions on San Diego real estate investing, buying a house with your 401(k) money, and required minimum distributions - and they talk beer, tariffs, the inverted yield curve, and Friends. Transcript and show notes: http://bit.ly/YMYW-199

7 Tips and Financial Benefits for Military Families - 198 Dec 04, 2018

Ellie Kay and Bethany Bayless (Heroes at Home, The Money Millhouse podcast) share some of the financial challenges America's military families face that civilians may not think about - along with some tips and benefits to help them make the most of their money. Plus, Joe and Al answer your money questions: when should you claim Social Security to avoid any changes for the worst that the government might make to the system? Is a Roth 401(k) or a traditional 401(k) better for dealing with taxes and inflation? And, Joe, Al, and Andi share their Cyber Monday shopping stories. Transcript & show notes: http://bit.ly/YMYW-198

Mobile Home Parks: Is This Undiscovered Real Estate Investment Right For You? - 197 Nov 27, 2018

Jefferson Lilly from Park Avenue Partners and the Mobile Home Park Investors podcast and LinkedIn group tells us why he thinks mobile home parks are the best real estate investment available. Plus, Joe Anderson, CFP® and Big Al Clopine, CPA answer your money questions on investing in natural resources, asset location when investing $50,000 cash, how to plan for retirement in the event your pension disappears, TSP allocation when retiring in 20 years, and transferring your 401(k) into your spouse's solo 401(k). Transcript & show notes: http://bit.ly/YMYW-197

Living Beyond Your Means Now? You'll Live Beneath Your Means In the Future - 196 Nov 20, 2018

JP Morgan Chief Global Strategist Dr. David Kelly discusses the mid-term elections, market volatility, interest rates, tariffs and trade wars, Brexit, his 2019 economic predictions and what all of that means for you and me. How should you be invested now? Dr. Kelly also gives his opinions on value versus growth stocks, international stocks versus US stocks, emerging markets like China, and other asset classes like bonds and commodities. Plus, Joe and Big Al have money-saving year-end tax strategies and answers to your money questions: should you sell stock to pay back taxes, and should you take investing advice from one of the big name investment companies? The answer might surprise you. Transcript and show notes: http://bit.ly/YMYW196

Do These 9 Simple Things to Improve Your Retirement - 195 Nov 13, 2018

Dr. Stephen Wendel, Head of Behavioral Science at Morningstar, talks about the challenges that keep us from making good investing decisions, and 9 simple actions we can take to create a better retirement for ourselves. Plus, a quick look at how companies helped get out the vote for the midterm elections and some market movers and shakers. And of course, answers to your money questions: Can you contribute the max to both a Roth and a traditional IRA, then do a conversion in the same year? If you roll a 401(k) with after-tax assets to a Roth, will the pro-rata tax rule apply? And if you're living comfortably within your means in retirement, is it wise to invest? Transcript and show notes at http://bit.ly/YMYW-195

Apple, Spotify and RMDs Feeling Volatile Markets - 194 Nov 06, 2018

How the most volatile month of the year affected Spotify and Apple, and how to avoid volatile markets and sequence of returns risk affecting your required minimum distributions. Plus, should a self-employed small business owner contribute to a solo Roth 401(k)? If you max your Roth IRA contributions and receive a company match, is that over-contributing, and how is that match taxed? And what should you do about that variable annuity you're locked into? Transcript and show notes: http://bit.ly/YMYW-194

Why Market Corrections Are a Good Thing - 193 Oct 30, 2018

The market has been in correction territory more than once over the past week, and Joe and Big Al explain why that's a good thing. Plus, is the three bucket investing and withdrawal strategy good for large portfolios? What's the real value of your net worth? You'll think the fellas have lost their sanity when you hear them talking about ways to protect your sanity and your money as you age. And, on the heels of the Red Sox winning the World Series, Big Al's got some baseball and money stats. Transcript and show notes: http://bit.ly/YMYW-193

Jean Chatzky on the Big Shift to Women in Financial Power - 192 Oct 23, 2018

Jean Chatzky (NBC's Today Show) talks about HerMoney.com, her new project giving women the confidence to lead the charge into the financial future. Plus, what women get wrong about money, how automation can help our health and our wealth, and why the gig economy isn't helping. Joe and Big Al discuss the Uber IPO, taking RMDs from your IRAs, paying all cash for real estate investments, 1099 versus W2 employment, and why one woman's "personal tax shelter" was rejected in tax court. Transcript and show notes: http://bit.ly/YMYW-192

Tempted to Panic and Sell? Do These 3 Things Instead - 191 Oct 16, 2018

Brian Perry and Larry Swedroe on market volatility, whether, as President Donald Trump said, the Fed is crazy, and what 3 things you should do next to be like the greatest investor of all time, Warren Buffett. Plus, answers to your questions: can you roll a 401(k) into a home purchase? What's a good allocation of stocks vs. bonds? And find out why Joe says to contribute to your 401(k) plan regardless of the investment options and fees, and why he thinks Suze Orman is crazy and out of her mind! Transcript and show notes: http://bit.ly/YMYW-191

4 Roth Conversion Options for Tax-Free Portfolio Growth - 190 Oct 09, 2018

Trump tax cuts are slated to sunset in 2025, but the House has passed the GOP bill to make them permanent. Life insurance settlements, or "Death Bonds," are being offered as a "solution" to senior bankruptcies. Four different Roth conversion options to avoid a tax bracket jump, with a caveat. And answers to your questions: Will the IRS take FICA taxes out of those conversions? What's the deal with required minimum distributions, qualified charitable distributions, and Roth IRA rollovers? Plus, Joe and Big Al go off on self-directed IRAs. Transcript and show notes at http://bit.ly/YMYW-190

IRA Basics: What You Need to Know About Individual Retirement Accounts - 189 Oct 02, 2018

How much do you know about the individual retirement account, also known as an IRA? In today's podcast, the basics: contributing to an IRA, SEP IRAs and SIMPLE IRAs for small business owners, self-directed IRAs, and IRA mistakes to avoid. Plus, Joe and Big Al answer your questions - like what's the return on an IRA? Why is owning real estate in an IRA a terrible idea? Transcript & show notes: http://bit.ly/YMYW-189

Risks and Rewards of Vacation Rentals and Real Estate Investing - 188 Sep 25, 2018

Cubert from AbandonedCubicle.com shares his plans for using real estate, including AirBnB and VRBO vacation rentals, on his path to financial independence at the age of 46. Is it worth the risk? Plus, Joe and Big Al answer your questions about real estate investing: will it help you minimize taxes in a high tax state? And how can you avoid capital gains when selling rental property? Transcript & show notes: http://bit.ly/YMYW-188

Trump Retirement Security Executive Order: Small Business Opportunities and Concerns - 187 Sep 18, 2018

Jeffrey Levine (Forbes, Kitces.com, BluePrint Wealth Alliance) on President Donald Trump's executive order on Multiple Employer Retirement Plans and required minimum distributions. Jeff also tells us how the IRS is throwing salt in the state and local tax deduction limit wound. Plus, will contributing to your retirement account lower your taxes and let you keep more take-home pay, and when should you file for Social Security or spousal benefits? Transcript and show notes at http://bit.ly/YMYW-187

Stop Spending Money the Wrong Way: 77 Days to Financial Happiness - 186 Sep 11, 2018

HumbleDollar.com's Jonathan Clements (former Wall Street Journal) helps us stop spending money the wrong way and shows us how to enrich our financial lives in just 77 days with his new book, From Here to Financial Happiness. Big Al has 3 things you need to do now if you want to retire in 5 years, and Joe and Al answer your questions: why are there required minimum distributions on employer-sponsored Roth accounts, and can Elizabeth's husband contribute to his defined benefit pension plan AND his company 401(k)? Transcript and show notes: http://bit.ly/YMYW-186

What You Need to Know About Social Security and Making Money - 185 Sep 04, 2018

Answering your questions on how collecting a paycheck or investing during retirement might affect your Social Security benefits. Plus, "the Goddess of Social Security," InvestmentNews contributing editor and nationally recognized Social Security expert Mary Beth Franklin goes over the basics of Social Security, claiming benefits as a single person, a married couple, a public employee - and are you eligible for retroactive Social Security benefits? Transcript and show notes at http://bit.ly/YMYW-185

How to Manage 8 Risks That Can Derail Your Retirement - 184 Aug 28, 2018

Plenty of risks threaten retirement, and today we focus on managing risks from longevity, inflation, sequence of returns, taxes, interest rates, and lost opportunity. Plus, Professor Jamie Hopkins from The American College and the New York Life Center for Retirement Income talks about how our risky investor behavior needs Rewirement (which happens to be the title of his most recent book), how a reverse mortgage can help, and why "set it and forget it" may also be a risk to retirement. Transcript and show notes at http://bit.ly/YMYW-184

Your 2018 Taxes: 10 Ways to Prepare and Save - 183 Aug 22, 2018

2018 taxes will be very different than previous years. We've got 10 ways to make sure you're properly prepared, and perhaps even reduce your 2018 tax burden. We'll talk about the "cumbersome and confusing" tax changes for small business owners. What exactly are QBI, 199A, and QCDs? Plus, we talk about the benefits of Roth IRAs quite a bit - but when might a Roth IRA be WRONG for you? And is it nuts to go with CDs in a traditional IRA? Transcript and show notes at http://bit.ly/YMYW-183

Morgan Housel: How to Cure the Investing Disease of Fear and Greed - 182 Aug 14, 2018

Morgan Housel (Collaborative Fund, former Wall Street Journal and Motley Fool) offers practical ways to determine your actual risk tolerance and perhaps help avoid the investing disease of fear and greed. And, listen to find out where you fall on Morgan's spectrum of financial dependence to financial independence. Plus, should you invest in a hybrid fixed indexed annuity? Is an indexed universal life insurance policy right for you? Transcript and show notes at http://bit.ly/YMYW-182

Are More Trump Tax Cuts and Big 401(k) & IRA Changes On the Way? - 181 Aug 07, 2018

More possible tax cuts from the Trump administration, and big changes coming to our 401(k)s and IRAs? Plus, If you had to buy and hold one stock for the rest of your life, or if you had to choose one investing style and stick with it for the rest of your life, what would you choose? Meb Faber from the Meb Faber Show podcast answers those questions and talks about his upcoming book, The Best Investment Writing, Volume 2. And we'll check in with Pure Financial Advisors' Director of Research, Brian Perry, CFP®, CFA® for a 2018 second quarter market update. Transcript and show notes: http://bit.ly/YMYW-181

Why Do You Need To Understand Financial Markets? With Marc Levinson - 180 Jul 31, 2018

Marc Levinson, author of The Economist Guide to Financial Markets: Why They Exist and How They Work explains how understanding financial markets can help you make fewer investing mistakes and improve everything from your home to your job to your portfolio. Plus, what does Tax Reform 2.0 have in store for us? What to do with a few extra bucks before they burn a hole in your bank account? Can you avoid taxes on an inherited annuity? Do SEP IRA's have ERISA protection from creditors, "like the OJ stuff?" Joe Anderson, CFP® and Big Al Clopine, CPA have some answers. Transcript and show notes at http://bit.ly/YMYW-180

Can Risk Revolutionize How You Work? With Joel Comm - 179 Jul 24, 2018

Joel Comm (best selling author, entrepreneur and co-host of the Bad Crypto Podcast) talks about his new book, The Fun Formula: How Curiosity, Risk-Taking, and Serendipity Can Revolutionize How You Work. Plus, should you quit a high paying job to be a DJ? Should you save for retirement or pay off student loan debt? Do you have to prove to the IRS that 529 plan money went to education expenses? And for show and tell, what little Joe and little Al did for cash before they became the self-made men and podcast hosts they are today. Transcript and show notes at http://bit.ly/YMYW-179

Michael Batnick: The Best Investors and Their Worst Investing Mistakes - 178 Jul 17, 2018

Even the best investors make terrible investing mistakes. Michael Batnick talks about his new book, Big Mistakes: The Best Investors and Their Worst Investments. Plus, should you sign up for Medicare, and which parts? And, Big Al's got 5 smart ways to collect more Social Security benefits, and the fellas answer the question, can you still take a lump sum from those benefits to buy a red Ferrari? Transcript and show notes at http://bit.ly/YMYW-178

50 Or Older? Don't Skip These 5 Key Retirement Questions - 177 Jul 10, 2018

7 Steps to Retire in 10 Years, 5 Key Retirement Questions You Need To Answer When You're 50 Or Older, 10 Frequently Asked IRA questions, and some questions answered, like, "The estate is in probate and the accounts are frozen, now what?" and, "Where should you invest any extra money you have left over each month?" (Oh, and Joe and Big Al bicker like they've been married for years!) Transcript and show notes at http://bit.ly/YMYW-177

Use This Quick Calculation to See If You're on Track for Retirement - 176 Jul 04, 2018

Are you on track for retirement? Big Al Clopine, CPA created a quick retirement calculation to help you find out. If you're a little behind in your savings, Big Al also has 3 ways to get caught up. Wondering if Joe contributed anything to this episode?? That would be a yes! We've got questions and Joe's got answers on the differences between the 403(b), 457(b) and 401(a), he clears up the whole Roth IRA 5-year clock thing, and producer Andi gets an answer to her question on doing a Roth conversion from her current 401(k) plan. Transcript and show notes at http://bit.ly/YMYW-176

How to Rock Retirement With The Retirement Answer Man - 175 Jun 26, 2018

The Retirement Answer Man, Roger Whitney, CFP® talks about his book, Rock Retirement: A Simple Guide to Help You Take Control and be More Optimistic About the Future (listen to find out how to get a free copy!) Also, in some states, you may be able to pay your state taxes as a charitable donation and get a tax deduction, but Joe and Al explain why you might want to be careful with that. Plus, 5 hidden taxes that could bite you in retirement, the fellas help a listener make the most of her passive losses, and what's the latest with the deductibility of home equity loans? Transcript and show notes at http://bit.ly/YMYW-175

Will Cryptocurrencies Disrupt Real Estate Investing? - 174 Jun 19, 2018

Cryptocurrencies have taken investing into risky, adventurous new territory over the past few years, and now a new blockchain-based real estate investing platform wants a place in your portfolio. Learn more about it and about Sam Ball, the young investor and Twitter influencer promoting it. Plus, how not to screw up your Roth conversion and legal ways to get tax-free retirement income. Transcript and show notes at http://bit.ly/YMYW-174

Life Insurance, Long Term Care, Annuities, and Ranting About Reddit - 173 Jun 12, 2018

A Reddit thread about getting sold life insurance when going to a life insurance company for financial planning gets Joe Anderson, CFP® ranting! To make sure Joe's insurance rant doesn't apply to you, and to help you avoid buying insurance you don't need, Paul Lim CFP® talks about term life insurance, permanent life insurance, long-term care, and annuities: what they are, when you need them, and how they fit into your overall financial plan. Transcript and show notes at http://bit.ly/YMYW-173

How Much Can You Really Spend in Retirement? - 172 Jun 06, 2018

Wade Pfau on the 4% rule for retirement withdrawals. How a risk-filled burrito can earn up to 11%. Joe & Big Al take on Dave Ramsey's advice to pay debt before saving for retirement and they debate real estate vs. bonds. IRA planning for the rest of 2018 to save on taxes - tell the grandparents to use RMDs for QCDs. Work remotely? Consider a move to Vermont. Lifestyles of the middle class in a new segment, "Where Does Big Al's Wife Anne's Family Live?" Transcript & show notes: http://bit.ly/YMYW-172

Jonathan Clements on The Secret to Defeating Ingrained Financial Failure Instincts - 171 May 29, 2018

Jonathan Clements (HumbleDollar.com, former Wall Street Journal columnist) on how to get from here to financial happiness and success, defeating the instinctual urges ingrained in us by our ancestors that often lead to financial failure. Plus, should you give your graduate the gift of a Roth IRA? Listen and learn why that gift could be worth $2 million. And what are the chances that you'll be subject to an IRS tax audit - by agent Will Smith?? Transcript and show notes at http://bit.ly/YMYW-171

Can Market Predictors Make You a Better Investor? - 170 May 22, 2018

Larry Swedroe, Director of Research at Buckingham Strategic Wealth and columnist at ETF.com, talks about how his views on active vs. passive investing, the value premium, market predictors and expected returns held up since he wrote his first book 20 years ago - and how he feels today about global diversification and alternative investments. Plus, Joe and Big Al talk dynasty trusts, for those with an estate like Secretary of the Treasury Steve Mnuchin, who is worth about $300 million. Transcript and show notes at http://bit.ly/YMYW_170

Sell in May and Go Away: Can You Time the Market? - 169 May 15, 2018

Nationally recognized mutual fund, index investing and asset allocation authority Paul Merriman gives us the truth on market timing versus buy and hold - and he explains why he still does both. Plus, answers to your questions on collecting Social Security and a pension, non-deductible, Roth and SEP IRA rollovers, Backdoor Roth conversions, and are there financial perks to getting married before the end of the year? Transcript and show notes at http://bit.ly/YMYW-169

3 Ways a Reverse Mortgage Can Supercharge Your Retirement - 168 May 08, 2018

Dr. Wade Pfau of RetirementResearcher.com returns to Your Money, Your Wealth® to share some incredible reverse mortgage strategies that can supercharge your retirement when executed correctly. He also updates us on the new rules for reverse mortgages, explains why they have traditionally gotten such bad press, and how they've changed. Transcript and show notes at http://bit.ly/YMYW-168

Money & Divorce: 14 Disastrous Mistakes That Will Steal Your Financial Dignity - 167 May 02, 2018

The financial lifeguard Christine Luken talks about her new program, Financial Dignity After Divorce, which will be especially useful if you make any of these 14 money mistakes during a divorce. Plus, how much the average couple will spend on healthcare costs in retirement, and with all this market volatility, is your 401(k) safe? And the fellas answer questions about buying a house with cash vs investing in a mutual fund, and paying into Social Security after you quit working so you can max out your benefit. Transcript and show notes at http://bit.ly/YMYW-167

From Consumer to Creator: How to Reach Financial Independence with Philip Taylor - 166 Apr 24, 2018

Philip Taylor, AKA PT of PTMoney.com, shares the method he used to reach financial independence as he transitioned from CPA to financial media mogul as the creator of the annual FinCon conference for financial media creators. Plus, 5 ways to turn retirement savings into income, how a big lottery win might affect your Social Security benefits, and if you dollar cost average into Bitcoin to buy winter parkas, how is that actually taxed? Transcript and show notes at http://bit.ly/YMYW_166

250 Creative Ways to Save and Make More Money with Nick Loper - 165 Apr 17, 2018

Nick Loper of Side Hustle Nation shares just a few of the 250 ways he's found that everyone from millennials to baby boomers can make more money and trim expenses in this new era of creative entrepreneurship and freelance work, from shuttling booze to making some bread teaching people to make bread. Plus, Joe and Big Al do the math for a listener who wants to know if they need to curtail some of their spending as they plan for retirement. Transcript and show notes at http://bit.ly/YMYW_165

How to Be Financially Alert and on FIRE at Age 36, Even With Market Volatility - 164 Apr 10, 2018

Michael from FinanciallyAlert.com reached Financial Independence / Retire Early, or FIRE, at age 36. He shares his inspiring success story of how being financially alert allowed him to transition from small business entrepreneur to stay-at-home Dad and FIRE blogger with a growing net worth of over $2M - and how he can coach you to FIRE too. Plus, market volatility is back, but Chuck Norris laughs in the face of market dips - and Brian Perry, CFP® has the Q1 market update. It's tax season and you might not get audited, but watch out for those penalties. And just how much should you have in Roth, tax deferred and taxable accounts at retirement? Show notes and transcript at http://bit.ly/YMYW-164

6 Things to Look For When Buying Investment Property with Joel Larsgaard- 163 Apr 03, 2018

Joel Larsgaard from the Pour Not Poor podcast (now called the How to Money Podcast) talks about drinking beer and simplifying your life to save money that you can put towards buying rental real estate. And, some things to drink about - er, think about - before you commit to that investment property. Plus, the best places to invest in commercial real estate, why early retirement might kill you, and Joe reminisces about his experience at a foam party in Mazatlan. Show notes and transcript at http://bit.ly/YMYW-163

She Saves $85,000 Annually. Learn Jamila Souffrant's Secrets -162 Mar 27, 2018

Jamila Souffrant from JourneyToLaunch.com explains how she can save $85,000 every year, and how you can save and invest more money too. Plus, Financial Planning Tips for Young Investors and the merits of buying company stock. And interest rates are on the rise - what does that mean for your bond portfolio? Show notes and transcript: http://bit.ly/YMYW-162

Ditch Your Debt: Robert Farrington's Student Loan Debt Movement - 161 Mar 20, 2018

Robert Farrington from TheCollegeInvestor.com has a goal of helping people eliminate a million bucks in student loan debt in the Month of March. Join the movement, ditch your debt and win prizes! Plus, Americans have reached record-breaking net worth - but which Americans? And, 4 ways you might be attracting a tax audit without knowing it. Show notes and transcript: http://bit.ly/YMYW-161

10 Commandments of Retirement from The Retirement Manifesto - 160 Mar 15, 2018

Fritz Gilbert from TheRetirementManifesto.com shares his 10 Commandments for Retirement - well actually it's 11, but that extra one is important! Plus, Big Al has 10 ways to pay less in taxes this year, and in future years. And Trump's steel and aluminum tariffs have set off more market moves, but could they also jack up the price of a Jack and Coke? Show notes and transcript: http://bit.ly/YMYW-160

16 Money Tips and Mind Tricks from Broke Millennial's Erin Lowry - 159 Mar 09, 2018

Broke Millennial's Erin Lowry shares her mind tricks for more effective saving and her clever tips for paying down debt. Plus, working the tax brackets with Roth conversions, some crazy options that may or may not work when you've contributed too much to your 401(k) to get the employer match, and how DIY investing can be like Joe's bad golf swing. Show notes and transcript: http://bit.ly/YMYW-159

Seven Secrets for a Happy, Successful Retirement with Jan Cullinane - 158 Mar 07, 2018

Best-selling author, retirement expert and fluent backward-speaker Jan Cullinane lets us in on how many of the Seven Secrets for a Happy, Successful Retirement have to do with money - and how many don't. And you won't have to understand backward speak to get it! Big Al's got a whole new mindset for happiness after visiting South America, why it might be a mistake to get married later in life - or at all if you're Joe - and the fellas discuss a gentleman who finds himself bored after early retirement. Show notes and transcript: http://bit.ly/YMYW-158

Pay Off Debt, Starve & Stack, Retire Rich & Happy with Jackie Beck - 157 Mar 02, 2018

How to retire rich and happy: the two income starve-and-stack strategy, losing the ego, and the Pay Off Debt by Jackie Beck app. Oh, and Rondo soda pop, and never saying the word "tissue." Joe and Big Al also talk a bit about retirement readiness and taxes. Show notes and transcript: http://bit.ly/YMYW-157

Don't Scream "Get Me Out!" How to Stomach Market Dips - 156 Feb 22, 2018

What happened to the market correction, what happens next, and how can you avoid hitting your GMO (get me out) point? Larry Swedroe of the BAM Alliance and ETF.com gazes into his crystal ball. Plus, 5 questions to ask your estate planner after the new tax law, and what happens to your social media estate after you die? Who will manage all those videos of Joe playing golf on Instagram?

6 Things to Help You Avoid a Miserable Retirement with Catherine Collinson - 155 Feb 15, 2018

Avoid a miserable retirement with 6 actions that can help you prepare for the retirement of your dreams, according to Catherine Collinson of the Transamerica Center for Retirement Studies. Big Al's got a list of 10 reasons people don't create a budget. Plus, the fellas cover the best states in which to retire, and they answer yet another question Trump's new tax law as it relates to the sale of a primary residence.

SPECIAL: Market Volatility and Corrections - 154 Feb 13, 2018

Welcome to stock market volatility. Today the market clawed back some of its big losses from last week's correction, but what's in store tomorrow or next week or next month? What should you be doing with your portfolio, and how will this affect your retirement? Joe Anderson, CFP®, Al Clopine, CPA and Brian Perry, ChFC® provide some guidance.

How To Successfully Retire at 41 with Chris Mamula- 153 Feb 11, 2018

Chris Mamula retired early - at age 41! He now blogs about his experiences at CanIRetireYet.com. How did he do it, after making a decade of retirement planning mistakes? Plus 5 Things to Consider Before Tapping Your Retirement Accounts, and the good, the bad and the ugly of the popular "guaranteed income" products known as annuities. But first, the fellas have a bone to pick with CNN Money about the confusing new business tax deduction.

7 Changes to Social Security You Need to Know - 152 Feb 04, 2018

Today on Your Money, Your Wealth, seven new changes to your Social Security benefits - Joe and Big Al talk about the good and the bad. Plus, how small business owners may be in danger of screwing up their Social Security, how the new tax law lets you save big money if you're taking required minimum distributions, and Joe's fear of commitment is further cemented by the story of a fella who lost 60% of his life savings in a divorce.

Bitcoin, Blockchain and Cryptocurrency: Everything You Need to Know - 151 Jan 28, 2018

Cryptocurrency expert and controversial crypto-celeb Amanda B. Johnson answers the most common altcoin questions: what is digital currency? What's a blockchain? Is Bitcoin safe? Why is Bitcoin so volatile? Should I own any cryptocurrency? Can cryptocurrency actually prevent "secret inflation"? Plus, how trading Bitcoin could ruin your mental health and 9 strategies to retire this year so you'll have time to ponder whether or not you've "made it" in America - and what the heck is BillyRock?

Opportunities, Challenges and Tricks Coming From Trump's New Tax Law - 150 Jan 21, 2018

Joe and Big Al weigh in on 10 retirement resolutions experts say you should make for 2018. We'll learn some new opportunities, challenges and potential tricks coming out of President Donald Trump's new tax law. We'll find out the secrets to Big Al's big wallet, and how Joe is unwillingly helping his boy Mikey cut expenses. And we'll hear one of the rare instances when the fellas kinda butcher the answer to an estate planning question. (Photo of Donald Trump by Gage Skidmore)

How To Capitalize On The Goldilocks Economy in 2018 - 149 Jan 14, 2018

Brian Perry, CFP®, CFA® from Pure Financial Advisors recaps 2017's global Goldilocks economy. Will the bull run continue in 2018? Should we change our asset allocation to prepare our stock and bond portfolios for a market slow down? Are you properly allocated? What would Jim Cramer do, and should you care?! Plus, tax filing season is approaching, and Big Al's Big Brain contains a whole bunch of stuff you need to know about the new tax law before you start working on those 1040s.

How To Tailor Your Retirement Income Strategy - And Why You Need To - 148 Jan 07, 2018

Retirement nest eggs have become bigger, but fixed income rates of return are low. How do you create a cash flow? What strategy will allow your investment portfolio to provide income throughout your retirement? Joe and Big Al explain what matters when tailoring your own personal retirement income strategy. Plus, determining in which type of accounts you should have your retirement savings, from where you should withdraw your required minimum distributions, and whether any of it will matter once the robots take over.

12 Things You Need To Know About Trump's New Tax Law - 147 Dec 31, 2017

How Trump's new tax law, the Tax Cuts and Jobs Act, changes state and local tax deductions, brackets, the child tax credit, medical deductions, property taxes, mortgage deductions, home equity debt, charitable contributions, itemized deductions, alternative minimum tax, residential gain on sale exclusion and small business taxes. Plus, the top things no one tells you about retiring, Social Security claiming strategies, and do Roth TSP and Traditional TSP dollars "commingle?" And the Ghosts of Joe's Christmas past, or "oh s***, Ruthie stole baby Jesus."

What You Need To Know Before You Buy or Sell Gold with Peter Hug - 145 Dec 17, 2017

Peter Hug from Kitco Metals, Inc. describes the four types of people that buy precious metals, how to best buy and sell silver and gold yourself, and whether these commodities are similar to cryptocurrencies like Bitcoin and Blockchain. Joe and Big Al talk permanent vs term life insurance and tax reform. Plus, holiday gift ideas to transform the quality of life for the retirees in your life: they get new tech, and you get your third grade report card and high school lettermen's jacket.

8 Ways To Avoid Holiday Debt Hangover & Save Big Cash with Laura Adams - 144 Dec 10, 2017

Laura Adams, host of the Money Girl Podcast, joins the show this week to give us eight ways to save serious cash, so we can avoid the holiday debt hangover. (Can't guarantee that you can avoid working out, though.) She also lays out how to tackling debt and whether you should lease your car or not. Plus, the latest tax reform news, and eight ways to create tax-free income. And is Joe going to start charging his dear sweet mother Ruthie rent when she comes to visit him from Minnesota?

9 Retirement Tips If You Don't Plan To Retire - 143 Dec 03, 2017

Retirement planning tips and benefits when you don't plan to retire. Plus, how much should you have saved for retirement at different stages of life, how much has the average millennial saved, and the Roth 5 year clock: should you get married so you can take advantage of the fact that your new spouse's Roth is already over 5 years old? And, should you really be asking marriage advice of Joe and Big Al?

Use These Tax Deductions Now, They May Be Gone In 2018 - 142 Nov 23, 2017

Recharacterizing your Roth conversion, getting that knee replacement, meeting with every client you have all across the country and more: Joe and Big Al cover many things you might want to do before tax laws potentially change in a big way come January 1. Also, Suze Orman thinks everyone should work until they're 70 - we'll find out what Walter Updegrave from RealDealRetirement.com and Money Magazine thinks about that, and we've got 20 retirement stats that will blow you away. Plus, Big Al reveals his secret man crush.

Trump Tax Cuts? False. Try Tax Increases. - 141 Nov 20, 2017

Actual news you can really use about the ever-changing landscape of tax reform, why Trump's promised biggest tax cuts ever are actually a tax increase for many of us, and how it will affect you. Plus, Joe and Big Al have a yarn with Joe's fair dinkum, true blue, Aussie fine arts painter mate, Pete Tillack, on finding your passions in life, couches at the bottom of swimming pools, and getting thrown out of Christmas parties. (photo of Donald Trump by Gage Skidmore)

A Last Minute Feel-Good Way to Reduce Your 2017 Taxes - 140 Nov 13, 2017

Elaine Martyn from Fidelity Charitable explains how donor advised funds can help others and reduce your 2017 taxes. Retirement jitters, a retirement crisis, and 7 ways to teach your kids the value of saving for retirement to help them avoid both the jitters and the crisis. Plus, is there any way to undo rolling a 401(k) into a 403(b) annuity? And can Joe explain why a 60/40 mix of stocks and bonds isn't necessarily the best way to go - without snapping?

Six Secrets to Living A Luxe Life & Still Saving Money - 139 Nov 06, 2017

The Luxe Strategist offers six secrets to splurging on nice things while still saving 50% of your income. Joe and Big Al cover the latest on Trump tax reform, the retirement crisis, 7 Retirement Catch Up Strategies for Lifelong Procrastinators, and why caller Maria maybe shouldn't trade options. Plus, the fellas confess to their worst impulse purchases.

Losing Money Sucks. Time For Asset Protection with Doug Lodmell - 138 Oct 30, 2017

Asset protection attorney Doug Lodmell has the secrets to keeping your money safe in the event of a lawsuit. Social Security benefits and 401(k) contributions are going up, but the 401(k) thing may also be a nightmare. Al's got 6 myths about freezing your credit in the wake of the Equifax double debacle, and the fellas answer your emails on when to take RMDs, family real estate entanglements, and how not to self-deal in your Roth IRA, because that's illegal.

FIRE & The Retirement Manifesto: What Will You Do With Your Free Time? - 137 Oct 23, 2017

Fritz Gilbert, blogger at TheRetirementManifesto.com, one of the fastest growing financial blogs on the internet, talks about the Financial Independence / Retire Early or FIRE movement, and how to make the most of your retirement. Also, three tax tricks just for retirees and more on the Trump Administration's proposed tax reform. Plus, Joe and Big Al answer calls and emails on donor advised funds, day-trading, and risk tolerance vs risk capacity.

How To Rescue Yourself From Financial Rock Bottom with Christine Luken - 136 Oct 16, 2017

Financial Lifeguard Christine Luken explains how she used Mindful Money Management to rescue herself when she hit financial rock bottom, and how you can, too. Joe and Big Al answer questions on when the magic of compounding is gonna kick in, Roth conversions, required minimum distributions and how Trump tax reform will affect both. Plus, paying off the mortgage in retirement, marrying up for a better Social Security benefit, Joe's drinking and college football watching habits, and skydiving at age 90.

Trump Tax Reform: More Jobs, Fairer Taxes, Bigger Paychecks? - 135 Oct 09, 2017

Will the changes to tax brackets, deductions, exemptions, the alternative minimum tax, estate tax, individual taxes, small business taxes, corporate taxes and expenses in Donald Trump's "Unified Framework For Fixing Our Broken Tax Code" proposal provide more jobs, fairer taxes, and bigger paychecks as promised? Plus, Important Steps to Take in the Last 10 Years Before Retiring, and the financial dangers of fly-fishing with the wrong beer in retirement.

Millennial Money Founder Side-Hustled To a Million In 5 Years - 134 Oct 02, 2017

Millennial Money founder Grant Sabatier on how extreme saving and the art of the side hustle took him from $2.26 in the bank to a net worth of $1 million in just 5 years. Plus, 7 things YOU should do to become a millionaire, what Trump's tax plan means for the middle class, whether you should pay off the mortgage or save for retirement, and a whole bunch of Star Wars nonsense.

The Truth About Reducing Your Taxes Through Charitable Giving - 133 Sep 25, 2017

In the aftermath of natural disasters at home and abroad, Elaine Martyn from Fidelity Charitable explains how donor-advised funds can make for tax efficient, high impact giving. Plus, how to protect yourself from identity theft following the Equifax security breach, financial tips for the five stages of your relationship, soap opera estate planning, Joe and Big Al's beer tastes, and biker fashion.

3 Dimensions of Expected Returns with Apollo Lupescu - 132 Sep 18, 2017

Apollo Lupescu of Dimensional Fund Advisors explains how risk and expected returns are affected by size, price and profitability of a company, why the latest from President Trump shouldn't affect our investing choices, how diversification can protect us from market downturns, and how our fear and greed have us tripping over our portfolios. Also, emails and phone calls on timing retirement and saving while pregnant, plus 6 Last Minute Retirement Strategies and some retirement tips for our younger selves.

Mind The Gap: How To Make More Than You Spend In Retirement with J David Stein - 131 Sep 11, 2017

J. David Stein, host of the Money for the Rest of Us podcast, on managing emotions when it comes to investing and market volatility, and how to Mind the Gap between income and spending in retirement. If that gap is too large, we've got 99 side hustles that can help you make some cash. Also, 6 Tax Planning Tips to Consider for 2017, withdrawing from a Roth to fund college, and cost basis of stock held in trust for beneficiaries.

How to Turn $3,000 into $50 Million - 130 Sep 04, 2017

Investing authority Paul Merriman explains how to turn $3,000 into $50 million and talks to Joe and Big Al about value vs growth companies, market timing, choosing the right mix of stocks, bonds and other investments, and which stocks don't beat even Treasuries in the long term. Plus, The 10 Best - and Worst - Places to Retire, Ways to Fund Children's Education, and how to minimize taxes in retirement.

How To Fix Retirement Savings and Social Security with Robert Pozen - 129 Aug 28, 2017

Harvard Business School Senior Lecturer and Brookings Institution Senior Fellow Robert Pozen suggests fixing the retirement savings crisis with the Automatic IRA, and using Progressive Indexing to fix Social Security. Joe and Big Al discuss 6 Ways to Survive Retirement Income Shock, recourse versus non-recourse loans, RMDs on annuities in a 401(k), the difference between stocks that pay dividends and those that don't, and Aretha Franklin's plans for retirement.

Exposing Wall Street Marketing BS - 128 Aug 21, 2017

BAM Alliance Director of Research and author Larry Swedroe exposes what he calls "Wall Street marketing BS" about active management, dollar cost averaging - which he says is a dumb strategy - and more. Plus, 5 Mistakes to Avoid in Retirement, an update on the Department of Labor Fiduciary Rule, and… Pikachu eggs.

3 Retirement Tips From the Very Rich with Walter Updegrave - 126 Aug 07, 2017

Walter Updegrave from RealDealRetirement.com analyzed a recent survey of the needs, goals and concerns of very wealthy investors, and shares some useful retirement tips for the rest of us. Also, 12 Common Sources of Tax Free Income, 4 tax breaks that may be on the chopping block, the basics of Medicare, and Medicare mistakes. Plus, Joe still wants to grow a 'fro, and who doesn't like the Eagles? (hint, it's Big Al.)

Finance For Normal People with Meir Statman - 125 Jul 31, 2017

Meir Statman, professor of finance at Santa Clara University and author of Finance For Normal People: How Investors and Markets Behave tells Joe and Big Al how smart people can avoid doing stupid things when it comes to investing. Also, are you house rich but cash poor as you approach retirement? The fellas have some strategies for making use of that home equity to create some additional retirement income.

6 Values to Fuel Business Growth and Achieve Work Life Balance with Scott Ford - 124 Jul 24, 2017

Scott Ford, co-author of The Sustainable Edge: 15 Minutes a Week to a Richer Entrepreneurial Life tells Joe and Big Al how he and co-author Ron Carson achieved faster business growth and a better work/life balance. Also, can you avoid state taxes in retirement by getting a PO box in a no state tax state? Plus, 10 timeless financial tips and 4 documents you'll want for a solid estate plan.

Top 10 Tax Saving Strategies - 123 Jul 17, 2017

The Top 10 tax saving strategies of the last 25 years: From tax loss harvesting to 529 education savings plans. From LLCs vs. S-Corps to asset location (that is, what type of assets you put in what type of accounts). From charitable giving to estate tax planning, and then some. Also, an overview of what happened in the market in the second quarter, and titans, tritons, sun gods and mermen.

Is Stock Picking Dying Because There Are Fewer Stocks? - 122 Jul 10, 2017

Financial researcher Larry Swedroe offers several reasons you may not be getting the returns you've enjoyed in the past, and he challenges Jason Zweig's assertion in the Wall Street Journal that it's because there are fewer stocks to choose from. Plus, 4 Ways To Reduce RMD Taxes - what are QCDs and QLACs, anyway? And, can you retire at 60 when you're 43 and have no savings? How do chauffeurs and ambulances play into that equation?

Are You Retirement Ready? Calculate Your Power Percentage To Find Out - 121 Jul 03, 2017

USA Today columnist Pete The Planner tells us how to calculate our Power Percentage for retirement readiness, and how to set house rules to get on the path to a successful retirement. Plus, 8 benefits of claiming Social Security later, how a Roth 401(k) may give you more purchasing power in retirement than a traditional 401(k), and Joe wants to grow a fro.

Money Secrets of the Super Wealthy With Paul Sullivan - 120 Jun 26, 2017

Paul Sullivan, author of The Thin Green Line: The Money Secrets of the Super Wealthy tells Joe and Big Al how the decisions you make about your money can put YOU in the wealthy club. Plus, how should you prepare for President Trump's "biggest tax cut ever?" 3 things you may be getting wrong about retirement planning, and international taxation if you're planning to move out of the country in retirement.

Want To Be Stacking Benjamins? Do Nothing - 119 Jun 19, 2017

Guest Joe Saul-Sehy of the Stacking Benjamins podcast explains the value of having a financial planner (while avoiding his stalker, Your Money, Your Wealth host Joe Anderson.) Joe and Big Al discuss what the Department of Labor fiduciary ruling means to you and 10 steps to get ready for retirement. They also answer questions about saving for retirement as a self-employed person and whether you should talk finances with your girlfriend before moving in together.

7 Mistakes New Real Estate Investors Make with Alex Goldstein - 118 Jun 12, 2017

Alex Goldstein, author of No Nonsense Real Estate, offers 7 Mistakes New Real Estate Investors Make. Joe and Big Al discuss 3 ways to sell your real estate, Social Security taxation, and 7 Social Security mistakes to avoid. Plus, potential ways to fund Trump tax reform, and who pays for weddings these days?

Using Reverse Mortgages To Secure Retirement with Dr. Wade Pfau - 117 Jun 05, 2017

Dr. Wade Pfau reveals new research on the reverse mortgage as an insurance policy and investing tool, and discusses the 4% rule for withdrawing retirement income from your portfolio. Plus, Joe and Al have 10 tips to boost retirement savings, the pros and cons of rolling your 401(k) into an IRA, long term care tax strategies, the latest on the Department of Labor Fiduciary Rule, Prince's $250 million estate planning mistake, and who is better at investing, men or women?

Beat The Market, Save, Retire At 30? | Rob Berger - 116 May 29, 2017

From stock picking to retiring at 30, Rob Berger spills secrets learned in 10 years hosting The Dough Roller Money Podcast. Joe and Big Al talk about market volatility caused by President Trump's potential tax cuts, healthcare plan and proposed budget, and they cover 5 "fatal error" type inherited IRA mistakes, the merits of Star Wars merch, Johnny Depp's compulsive spending habits, and how joining a nudist colony may help your wallet.

The Value of Debt in Building Wealth | Tom Anderson - 115 May 22, 2017

Author Tom Anderson discusses the value of debt in wealth building through the four phases of life. Joe and Big Al go over 6 common myths that can mess up your retirement, and how much you need to save in order to have $1 million when you retire. Also, how will making a large IRA withdrawal affect your taxes, Medicare and Social Security? What are the pro-rata rule and aggregation?

The Investing Lie Wall Street Needs You To Believe - 114 May 15, 2017

Larry Swedroe, author of "Think, Act and Invest Like Warren Buffett," explains Wall Street's passive investing lie and what kind of returns you can really expect. Plus, how he relates investing performance to Babe Ruth and Roger Federer. Also, 5 Things Parents Need To Teach Kids About Money from Jack Kosakowski, President and CEO of Junior Achievement, 10 Retirement Planning Moves To Make in your 20s, and a closer look at Donald Trump's tax outline.

Low Cost, Diversified, Tax Efficient Funds That Trade Like Stocks: Are ETFs Right For You? - 113 May 08, 2017

Daniel Prince, CFA (BlackRock) explains exchange traded funds and what the future holds as investing evolves. Will Trump's new tax plan simplify taxes and spur economic growth as promised? If you're one of the 10,000 boomers a day now reaching required minimum distribution age, how do you avoid screwing it up? Why consider making a Qualified Charitable Distribution? And which is safer: Treasury bills or fixed indexed annuities?

Investor Psychology: You Can Be Right And Still Be a Moron - 112 May 01, 2017

Are you a fearful moron when it comes to investing? Can you invest in LGBT rights and gender equality? Is today's market forgetful? Behavioral finance expert Dr. Daniel Crosby, author of "The Laws of Wealth," discusses. Joe and Big Al consider The Biggest Tax Cut Ever, 7 Common Investor Mistakes, Ric Edelman's Social Security solution, and your 401(k), Roth IRA and Social Security questions.

The Trump Effect On The Markets - 111 Apr 17, 2017

Investor optimism reached a 17 year high with the Trump Effect and emerging markets, but what does that really mean? Joe thinks being emotionally invested in your portfolio may serve you better in the long run. Al quizzes Joe on 6 basic retirement questions most Americans can't get right. Plus, gifting a Roth IRA to a grandchild, whether to sell a losing stock, and contributing to a Roth IRA after leaving employment.

10 Tax Mistakes That Could Cost You Huge Penalties — Or Worse - 110 Apr 10, 2017

The pros and cons of taking Social Security before full retirement age, tax mistakes that could cost you huge penalties or worse, IRA myths, the morality of found money, and what Joe and Big Al know and love about social media. The fellas also answer emails about making 40% annual returns on your investments, and sound strategies for putting inherited IRA money into a Roth.

6 Steps To Get Super Rich & Work Your Wealth | Mary Beth Storjohann - 109 Apr 03, 2017

Mary Beth Storjohann, author of Work Your Wealth, helps millennials wrap their heads around financial basics. Joe and Al discuss a proposal to cut the corporate tax rate by taxing 401(k) gains, and spotting an IRS phone scam. Also, answers to questions on LLC vs. S-corp income, deductions for traditional IRAs, and taking a personal loan for the downpayment on investment property. Also, Big Al lists 6 steps to get SUPER rich.

Understanding Social Security & Donald Trump's Tax Return - 108 Mar 26, 2017

Social Security expert Mary Beth Franklin explains the current claiming rules. Joe and Big Al offer tips for managing taxes and they answer emails on rollovers, Roth IRA, 401(k), debt, and building a stock portfolio. And from sole proprietorships to real estate; alternative minimum tax to capital gains and losses, the fellas analyze the tax return of one Donald J. Trump.

Teaching Kids Economics With Author Michelle Balconi - 107 Mar 20, 2017

Our guest is Michelle Balconi, who co-authored the children's book Let's Chat About Economics! with economist Dr. Arthur Laffer. Joe and Big Al debunk retirement myths, discuss 8 things most Americans don't know about retirement, and answer emails on Roth IRAs, 401(k)s, and investing. Also: Joe is retiring to Togo to manage the fortune of an email scammer, and the fellas muse on Anthony Weiner's use of Snapchat.

6 Small Business Retirement Plans From Easy to Complicated - 106 Mar 13, 2017

Six small business retirement plans from easy to complicated, including the SEP IRA, SIMPLE IRA, Solo 401(k) and defined benefit plan. And, how to calculate your "power percentage" for retirement readiness (here's a hint, it involves adding up savings and old debt payments and dividing that into your income.) Plus, Joe and Big Al explain how buying expensive cologne online relates to behavioral finance.

8 IRA Mistakes That Can Mess Up Your Retirement - 105 Mar 06, 2017

8 IRA mistakes to avoid, the most expensive purchase you'll ever make, the best state tax breaks for retirement and how to prioritize where you save, to maximize what you save. Plus, Joe and Al answer questions on advisor credentials, the 60 day rollover rule, and which is safer, T-bills or fixed indexed annuities?

Portfolio Diversification Using Factor-Based Investing - 104 Feb 27, 2017

Larry Swedroe from Buckingham Strategic Wealth talks about factor-based investing for a widely diversified portfolio, and the difference between alpha, beta and smart beta. Seven tax planning tips for millionaires and those who want to be millionaires. Joe and Big Al talk about Social Security and the often-overlooked family benefits. And, the fellas answer emails on SEPP, 72(t), IRAs, 8606's, 1040's and other mysterious numbers and acronyms.

Do You Really Need a Financial Advisor? - 103 Feb 20, 2017

The value of a financial advisor (aka "Advisor's Alpha") and a discussion of target date funds with Don Bennyhoff from Vanguard, estate planning and the difference between a will and a trust, and Joe and Big Al answer emails on Roth conversions, taxation on day-trading stocks, tax write-offs on retirement contributions, and why some great companies have low stock prices. Plus, the fellas discuss a recent survey where millennials said they'd rather disclose a sexually transmitted disease to a potential partner than to reveal their debt. Original publish date February 11, 2017. Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 01:00 - Young Americans Would Rather Disclose Their STDs Than Their Debt 12:11 - The Importance Of An Estate Plan: Estate Planners 11 Tips for the New Year 26:47 - Should I Convert to Roth as Quickly As Possible or Over Time? 32:41 - Interview with Vanguard Senior Investment Strategist Don Bennyhoff on Target Date Funds and Advisor's Alpha 48:00 - How will my profits and loss from day trading be taxed at the end of the year? 50:46 - Can I still deduct a maximum amount of taxes on a traditional IRA if I contribute to a 401(k) plan? 55:51 - What is the best way to leave retirement accounts to children and minimize our RMD tax implications? 1:00:43 - Why do some companies have a lower stock price than other, less profitable companies?

How To Retire Early and 7 Retirement Rules For Anyone Over 50 - 102 Feb 13, 2017

How to retire early - like, really early - and real estate investing with Andrew Fiebert from the Listen Money Matters podcast, Seven Essential Retirement Rules for Anyone Over 50, and Joe and Big Al answer emails about target date funds, making the most of your pension income, buying Mom's house rather than inheriting it and determining capital gains on the sale of a rental. Original air date February 4, 2017. Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 00:50 - Department of Labor Fiduciary Rule: What It Means for You 10:48 - 7 Retirement Rules For Anyone Over 50 30:32 - Stocks, Bonds and Cash: How to Allocate Pension Income Assets 36:50 - How to Retire Early, with Andrew Fiebert from Listen Money Matters podcast 47:31 - Real Estate Investing Tips 51:18 - How to Manage Mom's Financial Assets and Tax Planning 56:08 - How can I determine capital gains tax from the sale of a rental property? 01:02:15 - What do you think about target date funds?

Stretch IRA's and The Business of Family - 101 Feb 11, 2017

Kiplinger's Retirement Report editor Rachel Sheedy tells Joe Anderson, CFP® and Big Al Clopine, CPA how to inherit a retirement account without paying a boatload of taxes all at once. Family, Inc. author Doug McCormick talks about how to use sound business principles to make the most of your family's money, and the fellas answer emails about retirement contribution limits, taxation on stock dividends and splits, and the voodoo of overfunding life insurance. They also discuss Social Security and Medicare changes in 2017, and the do's - and dont's - of saving for retirement.

00:00 - Intro 01:00 - 2016 Market Recap 07:39 - The Stretch IRA Explained, with Rachel Sheedy from Kiplinger 23:51 - 5 Ways to Become an Extreme Saver 30:20 - 2017 Social Security Changes 36:03 - Family, Inc. With Doug McCormick 47:16 - Answers to Money Questions 48:03 - I am currently contributing a company sponsored 401(k) plan. Can I also contribute to a Roth IRA? 50:52 - Are stock dividends and stock splits taxed? 56:06 - I've heard I can use life insurance like a Roth. How do I do this? And is it a good idea?

8 Proven Ways to Boost Your Retirement Income - 100 Jan 28, 2017

With so many retirement planning strategies and the plethora of information on the internet, it can be hard for some to prioritize where to start when it comes to planning for their retirement. Joe Anderson, CFP® and Alan Clopine, CPA share eight proven ways to boost your retirement income. Original publish date January 28, 2017 (hour 2). Note that content may be outdated as rules and regulations have changed.

02:02 "After age 70 ½, you cannot do an IRA contribution but you can do a Roth IRA contribution."

04:49 "Why do we not want to solely focus on dividend paying stocks? There's a lot of risk involved."

07:52 "If you are in a high dividend strategy and you don't necessarily need the income, you may want to readjust and be more sophisticated in your strategy."

10:18 "Delay your retirement by a few years…sometimes we run analyses for people if they retire at 65 versus 68 and it's incredibly different because what happens in a lot of cases is people are in relatively high earning years so they're putting maximum amounts in their 401(k) and getting maximum matches from their employers."

12:17 "When you add the Social Security to components, sometimes working just a few more years could add ten years to your portfolio."

12:35 "See whether a reverse mortgage makes sense for you…we did a webinar on home equity and that was one of the things we talked about."

17:59 "Can I claim a loss from my Roth IRA? I have a Roth IRA open for over 10 years now. I have contributed about $15K, but I lost around 80% of it due to some stocks that I invested in. Can I claim this 80% lost in my tax return? I know that I can claim up to $3,000/year for capital losses in regular investment, but can I claim my losses in the Roth IRA when I withdraw the money, or sell the stock(s)?" *Question from Investopedia Advisor Insights

18:35 "Once any dollar goes into a Roth IRA or regular IRA, the capital gains rules don't apply anymore, so you don't get to claim the gains or losses."

20:26 "It's difficult to get money into a Roth IRA because a) there are contribution limitations…b) if you convert money, that's unlimited but realize that you're paying tax as you convert those dollars."

29:35 "Should I retire early to take care of my parents? Within the next six months, I plan to quit working so that I can relocate and take care of my parents. I will be 50 years old at that time. I have no debt, am not married, and have no children. All of my living expenses will be paid for by my parents as compensation for taking care of them. In addition, I have a $700,000 nest egg. Many friends and colleagues are telling me I am ridiculous to retire so early. I don't agree. What is your opinion?" *Question from Investopedia Advisor Insights

31:44 "Well, how bad of shape are mom and dad? Are they going to live another twenty years or two years? If they're going to live another twenty years, then sure, go for it."

32:53 "This may not be forever; you can always go back to work."

7 Reasons to Say Yes to a Roth IRA - 99 Jan 28, 2017

How do you get motivated to save for retirement? Joe Anderson, CFP® and Alan Clopine, CPA share smart saving tips for retirement then shed light on why you shouldn't depend solely on your pension for future income. They close the hour with seven reasons why you should say yes to a Roth IRA. Original publish date January 28, 2017 (hour 1). Note that content may be outdated as rules and regulations have changed.

02:06 "I want to go over in this segment a few ways to motivate yourself to save more for retirement, and I think this is something that's true for all of us – whether you've saved little, none, or a whole lot."

04:48 "No matter where you're at – whether you're in your thirties or in your sixties, you want to be saving as much as you can because retirement is going to happen."

07:46 "If I save $10,000 after tax (let's say I have a Roth component in my 401(k) plan), I forgo the $2500 savings today and then it grows to $100,000 and then [when] I pull out the $100,000 I don't pay any tax at all. Let's assume we're in that same 25% tax bracket – that's a $25,000 savings. So I forgo the $2500 to save $25,000 down the road, versus a $2500 tax deduction today and then down the road paying $25,000 in tax."

09:25 "If you have the discipline to save that tax savings and you're in a higher tax bracket, by all means, go for the pre-tax and get that deduction… take that $2500 and save it - put it in a Roth IRA as a contribution; that would be the best [case scenario]…people forget about this because they just spend it."

16:17 "A lot of companies, as ours, we do have a 401(k) and a match, but it's not the same amount as a pension plan."

17:05 "If you do have a pension, private or public – that doesn't necessarily mean you should just coast."

19:28 "The most obvious benefit of a Roth IRA is it can provide you with tax-free income in retirement."

22:56 "A couple of things when it comes to RMDs (required minimum distributions) – you don't necessarily have to sell the investment. You're taxed on it, but you don't need to sell it if it's in an IRA. You can transfer shares out and put it into a brokerage account."

27:36 "If you don't have a Roth, we would encourage you to at least open one up because then that starts your five-year clock."

28:06 "A Roth IRA can be a great compliment to other retirement accounts. A lot of people don't realize the power of this."

32:22 "Roth IRAs are great for estate planning as well because your kids get them tax-free as well."

The Value of Debt with Author Tom Anderson - 98 Jan 21, 2017

Joe Anderson, CFP® and Alan Clopine, CPA interview Tom Anderson, author of The Value of Debt in Retirement, to discuss why debt isn't always a bad thing in retirement. The Value of Debt placed #2 on Forbes List of Personal Finance Books Financial Experts Say Will Change Your Life. Plus, Joe and Al answer more email questions on-air. Original publish date January 21, 2017 (hour 2). Note that content may be outdated as rules and regulations have changed.

0:58 "We're answering email questions as well, and this is fitting for our next segment."

1:03 "I have a large 401(k) plus a pension. I want to retire before the end of 2017. I will be 62 years old in September. Would it be wise to pay off my car loan so I don't have any debt when I retire? Should I withdraw from my 401(k) to do this?"

2:56 "Maybe this will work for you…I would look at my income over the next eight, nine months and try to budget extra payments so that by the tenth month I can have it all paid off with my salary."

3:35 "A lot of people go into retirement thinking they have to have their mortgage paid off; that's not necessarily true."

6:28 Start of Interview with Tom Anderson

Joe (7:11) "Tom, let's talk first of all about the title [of your book], 'The Value of Debt in Retirement' – when you think of most financial pundits, that's the opposite take of what you might hear when you approach retirement."

Tom (7:27) "That's the general plan, is people are saying they need to rush in and get rid of all their debt before they retire – so we went with a more controversial title…we tried to put the math around it and explore that topic."

Joe (7:57) "Most individuals, as they approach retirement, don't necessarily take a look at both sides of the balance sheet. They might focus on the debt side a little too much where they pay extra on their mortgage payments and they have very little liquid capital to provide any type of retirement income, and they might think that will be a safer route approaching retirement where in actuality that might be the opposite thing they should be doing."

Tom (8:25) "That's exactly right…what happens is a lot of people find that they don't have enough retirement savings…while many people feel they've under-saved for retirement, what they're doing is they're rushing in to pay off their debt, and they're finding that they don't have the liquidity or flexibility or the resources to put them on track for retirement."

9:03 "Your listeners have to know that I don't think all debt is good."

Joe (9:37) "Right, it's figuring out what is good debt and what is bad debt. I think people just lump debt into one category and say 'no, it's all bad – I want to be debt-free' and then all of a sudden when they get into retirement they may have a paid off house but they have very little liquid assets and don't have the retirement income they need long-term."

Tom (10:09) "I would love for everybody to be able to pay off their house, but what happens is when you're getting close to retirement, until you have enough money to pay off all of your house, I suggest why pay off any of it, because it's a one-way liquidity trap."

10:34 "What readers need to be thinking about is how to protect the liquidity and flexibility and make sure there are enough resources; [consider] working with an advisor…"

Joe (10:55) "What are the right types of debt?"

Tom (10:58) "Any debt that has a rate of return or a cost of it less than what you think you're going to earn long-term in your portfolio…"

Joe (11:47) "Are there certain ratios that you take a look at?"

Tom (12:00) "When you retire, you basically have a pod of money that you're trying to create an income stream from in retirement…there's no clear math-compelling case that debt will add value. If you need to have between a 4% or 6% distribution rate – let's say I have $1 million and I want to spend $50,000 a year, then I show that a 30% debt to asset ratio actually can add value. Those people have to take risk either through investing in risky assets or debt…some debt, the right kinds of debt, the right way, can actually reduce that risk."

13:40 "It is a mathematical fact that debt can increase the rate of return in your portfolio. It is a mathematical fact that debt can reduce taxes; it is a mathematical fact that counterintuitively debt can reduce risk…it is a fact that this is not a guaranteed path and that you're basically choosing between two different risks."

18:36 End of Interview with Tom Anderson

19:34 "It's not the end of the world to have a mortgage these days, particularly because interest rates are low, and this is what we call good debt because your home should continue to appreciate."

24:54 "Which retirement account should we set up for our children? We would like to set-up accounts for our three kids, who are young adults. We are not sure if it is smart to make them wait until they are 59 1/2 years old. Would you recommend we set up a Roth IRA or a low cost index fund?"

26:45 "With a Roth contribution, the kids can always pull the money out – I would have them put it in a Roth IRA."

18 Questions to Ask Yourself Before You Retire - 97 Jan 21, 2017

Asking yourself these important questions before retiring helps rule out any unwanted surprises. Joe Anderson, CFP® and Alan Clopine, CPA dig into the email bag to answer your questions. Original publish date January 21, 2017 (hour 1). Note that content may be outdated as rules and regulations have changed.

2:48 "When you use debt properly, it can actually be pretty effective."

9:32 "Here are 18 questions to ask yourself before you retire…let's start with the first one: what does being retired mean to you?"

13:02 "Absolutely make sure you communicate what your retirement vision looks like to your spouse."

16:58 "What would you like to add to your life and eliminate from your life?"

20:19 "How do you feel about downsizing? A lot of our equity and net worth is pent up in our home."

25:06 "Should I recharacterize my Traditional IRA contributions to a Roth IRA?"

26:12 "Virtually anyone that's working and has earned income can do a regular IRA contribution as long as you're under 70 ½, however here are a couple stipulations…"

27:31 "If you're single and your income is in between $118,000 and $133,000 you can do a partial Roth contribution."

28:48 "You can do a Roth conversion regardless of your income level and age, and you don't have to be working."

30:33 "Recharacterization means you're undoing your contribution that you made."

31:36 "Control is everything when it comes to your money in retirement, because in retirement you actually do have more control over how much you pay in taxes [according to] which accounts you take money out of, and each account may be taxed differently."

The Thin Green Line with Author Paul Sullivan - 96 Jan 14, 2017

Paul Sullivan joins Joe Anderson, CFP® and Alan Clopine, CPA to discuss the biggest lessons from his book The Thin Green Line: The Money Secrets of the Super Wealthy on creating and maintaining wealth. Also in this hour: answers to financial questions. Original publish date January 14, 2017 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:38 "[With] the 60-day rollover, you can only do one per year for all of your IRAs (individual retirement accounts) so all of your IRAs are considered to be one account."

04:18 "I don't think this one is widely known, and when you have a 401(k) that has company stock and you roll it over into your IRA, you completely lose a strategy called net unrealized appreciation (NUA)."

08:07 Start of Interview with Paul Sullivan

Joe: (08:30) "Tell us the genesis of the book. It's the secrets of the ultra-wealthy – what did you learn and what are some of the things that we can give to our listeners?"

Paul: (08:58) "The gist of the book is this: how we think about money matters more than anything else…"

Joe: (10:15) "How did you come up with the title?"

Paul: (10:20 "If you think about the S&P 500 or your favorite stock index over the past 50 years – it starts low, goes high but it's not in a straight line, it's a little bumpy along the way. That's the thin green line; the people who are on top of it – they're wealthy, whether they make a little money or a lot of money. Everybody else is rich and poor so you could be at the very tippy top making a ton of money each year but you're really rich. The difference is freedom. The people who are wealthy are able to make all the decisions and choices that they want to make with their money. They're in control, they control life.

10:57 "The people who are rich – you can think in the most simple context – is someone who is wildly over-leveraged. They may make $1 million a year but they have $5 million in debt obligations. Life is going to control them."

Joe: (11:51) "So wealthy is not necessarily a dollar figure in your bank account – it's basically the control that you have within the wealth you've created."

Paul: (12:13) "It's all about having those choices and knowing that when you make them you're not endangering some of the essential things in your life."

Joe: (15:01) "Give us some tidbits about your own personal journey."

Paul: (15:54) "It's been an interesting journey but it gives me perspective on [the fact that] it (wealth) can go away, how do you make sure it does go away and more importantly, how do I talk to my kids and my kids' friends so they understand that a lot of this is decisions and being aware of the decisions you make; and just as important is your behaviors."

17:27 "You can save money, you can spend money, you can give it away – but most importantly, you can think about it, and it's how those four work together that I hope will allow people to make better decisions in their own lives."

19:35 "The Château Margaux is something I like, but if I'm going to have it once a year, there are other decisions I'm going to have to make to offset the splurge for that amazing bottle of French wine."

Joe: (20:02) "Where can people find more information about you?"

Paul: (20:04) "Go to my website: pauljsullivan.com or go to the New York Times website and type in my name."

20:23 End of Interview with Paul Sullivan

25:00 "I have a beneficiary IRA that I doubled by investing in Apple Stock. I now have sold 90% of that stock because I felt it was too risky to have all my eggs in one basket. I would like to primarily live off of the interest and not touch the principal ($900K) of my IRA. How would you suggest I invest to accomplish that? How should I invest for the long term inside my IRA?"

26:07 "I would look at this as more of a total return; I would look at a globally diversified portfolio total return, not just income."

29:11 "Should I diversify between different financial institutions? As a high net worth individual, should I diversify between financial institutions or should I just diversify within one organization such as Wells Fargo or Chase?"

30:55 "Well what if Chase or Wells Fargo goes out of business? You're investing in a security versus a bank."

33:56 "What tax rate will my mother have to pay on a cashed out IRA? I have a terminally ill mother who is 69 years old. She has a traditional IRA worth around $500K that she converted to an annuity at 4%. Her medical care requires increased cash flow to pay day-to-day bills. The company has agreed to cash out the full value of the IRA with 0 surrender fees. The company will not transfer the IRA to any other investment vehicle. If she takes the cash value, what are the tax implications? Her income last year was ~$30K and her effective combined federal and state tax rate was ~3%. Will she pay 3% on the $500K or the full federal and state rate of 41% (FED ~35 NC ~6)?"

34:55 "If you cash out an annuity, and the company is allowing you to do that without surrender, it can still stay out of an IRA."

35:37 "When you have effective rates like 3%...when you add additional income, now you're on the marginal rate concept which means whatever tax bracket you're currently in…that's actually the tax you're going to pay on the additional income."

*Email questions from Investopedia Advisor Insights

All About The 401(k) - 95 Jan 14, 2017

Joe Anderson, CFP® and Alan Clopine, CPA discuss why the father of the 401(k) regrets creating it. Plus, the worst mistakes you can make with your IRA and 401(k). Original publish date January 14, 2017 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

01:46 "[For today's topics,] I've got ten important considerations for 401(k) rollovers, and Ed Slott's three fatal IRA (individual retirement account) errors."

02:59 "Ted Benna, in case you don't know, is known as the father of the 401(k) and we was a benefits consultant with Johnson companies, and he was among one of the first to come up with the notion that American workers should set aside their own pay pre-tax for retirement."

04:02 "He and other early proponents dislike what the 401(k) has spawned. The tool was never meant to serve as the main means by which workers save for retirement, but that's precisely what it's become – it's increasing the financial risk for workers along the way."

08:25 "The other thing he doesn't like about the 401(k) is he says 'I helped open the door for Wall Street to make even more money than they were already making. That is the one thing I do regret.'"

11:36 "A majority of retirees rolled over their 401(k) to an IRA at retirement."

14:29 "Let's say you go back to an old company, you could roll all of your 401(k) into that new 401(k), that avoids the required distribution until you're retired."

20:03 "When you think of an appropriate globally-diversified portfolio with a rebalancing strategy, a rebalancing strategy simply means that whatever asset class you have that's done really well – you shave some of those profits off…and buy an asset class that hasn't done as well – you're constantly selling higher and buying lower by discipline...you take the emotion out of it."

22:57 "The true value-add of an advisor is to take a look at what the strategy is, what their plan is and coming up with the tax alpha if you will, because if you can reduce the overall tax liability of the income that you're trying to produce, that's more money – it's a rate of return. If you look at rebalancing when markets go up and down or sideways to keep that risk parameter based on your goals – that's huge."

29:24 "Here's another one (mistake) that's irreversible. This is when you have a non-spouse rollover…let's say you inherit an IRA from your father or mother and you roll it over into your own IRA…you may not realize this but it's a prohibited transaction. That's treated as a full distribution."

Family, Inc with Author Douglas P. McCormick - 94 Jan 07, 2017

Douglas P. McCormick joins Joe Anderson, CFP® and Alan Clopine, CPA to discuss the framework and premise of his book Family, Inc.: Using Business Principles to Maximize Your Family's Wealth. Also in this hour: Social Security changes for 2017 + answers to financial questions. Original publish date January 7, 2017 (hour 2). Note that content may be outdated as rules and regulations have changed.

6:27 Start of Interview with Douglas P. McCormick

Joe: (6:57) "Tell us a little bit about yourself and what made you write the book Family Inc."

Douglas: (7:12) "I'm an undergrad from West Point; I was an active duty army officer for five years and after that time decided a military career was not for me, so then I went back to business school at Harvard and graduated with a master's degree in finance and worked on Wall Street for a couple of years. In spite of all that great experience, I never had what I considered to be a good foundation in personal finance. Today, I think financial literacy is one of the biggest problems in America and our traditional education system is not doing a good job of teaching these principles.

7:49 For me, the Family Inc. framework is an elegant way to help people think about all the competing choices that they have out there with their assets and finances."

Joe: (8:15) "There are billions of books out there on personal finance and we still have a financial literacy problem. Why is your book different?"

Douglas: (8:23) "My objective is not to give you answers, but to teach people how to think so they can get their own answers. What is unique about Family, Inc. is that it provides people with a framework. The premise of the book is that all families could look at themselves as a business. Each family predominately has two big assets – they have their labor assets and they have their financial assets and the name of the game is to manage those assets, to do all the things you want to do in life and when it comes time to retire to have capital to support your consumption.

9:00 "I think the great thing about that framework is that businesses have been dealing with those kinds of decisions for many years…and when you look at the family that way it really allows you to borrow many of those tools and best practices that have been time-tested in business."

Al: (9:16) "Doug, give us a sample of what families ought to be looking for or looking to do."

Douglas: (9:22) "Let me give you some of the big mistakes. First of all, I think you can't really talk about financial independence or financial security if you're not thinking about how to maximize your labor potential…another thing the book does a good job on is helping people focus on the right time frame…to think about your performance not in terms of how you got paid this year but in terms of lifetime compensation – that's a very important change in time horizon."

10:26 "One of the things I really preach in the book is a family CFO's job is much broader than simply how you manage your investments or how you budget – it's things like managing your risk or training the next generation in the family to be good stewards of your capital and it's things like investment and education and entrepreneurship."

Joe: (13:34) "How would you do that calculation to see what the appropriate asset mix is in regards to equities?"

Douglas: (13:41) "Both Social Security and labor you can roughly calculate similarly which is you kind of make assumptions about either how long your working career is or how long you're likely to live…then you project your future income with a growth rate and tax rate…and you essentially discount that back with some adjustment for inflation. First of all, on familyinc.com there are calculators for both your labor and Social Security. Second, I promise you the estimate you come up with will be wrong – it's less about projecting a single number and more about thinking about that asset in the context of your overall plan because it's going to be directionally right."

Joe: (15:51) "What advice would you give our service men and women?"

Douglas: (15:56) "One of my primary objectives for doing the book is to support the military community and veteran community with a good framework to think about navigating transition. First of all, the big thing I'd say for the military community is you have to acknowledge that your circumstances are different from mainstream America, and so your plan must be different…it really starts with understanding those differences – the Family Inc. framework can also be applied to those circumstances."

17:35 End of Interview with Douglas P. McCormick

18:40 "I am currently contributing to a company sponsored 401(k). I contribute 8% (annual salary $60K), which comes out to $4,800 for the year. Can I also set up and contribute to a Roth IRA? If so, what amount can I contribute?"

18:59 "The answer is absolutely yes. With a Roth IRA, you can contribute $5500 per year. If you're 50 and older, you get a $1,000 catch-up so you can do $6,500. With the 401(k), it might have a Roth option in it. In that case, if you're under 50 you can contribute $18,000 total."

19:58 "If you fully fund a 401(k), you can fully fund a Roth IRA if you're under the income limits."

27:05 "Can I use life insurance like a Roth IRA? I make too much money to contribute to a Roth IRA. However, I would like to save more in a tax saving manner. I've heard I can use Life Insurance like a Roth. How do I do this? Is it a good idea?"

27:42 "Certain life insurance policies allow you to put more money into them than the actual life insurance premium so you start building up a cash surrender value. You can in many cases invest that how you see fit; it grows inside that insurance policy, there is no current taxation and then you get to a point where you retire and if it's a big enough balance you can borrow against that and it's tax-free."

Rachel Sheedy on Inheriting IRAs - 93 Jan 07, 2017

Editor of Kiplinger's Retirement Report, Rachel Sheedy joins Joe Anderson, CFP® and Alan Clopine, CPA to discuss inherited IRA (individual retirement account) rules & strategies for beneficiaries. Plus, how to become an extreme saver in 2017. Original publish date January 7, 2017 (hour 1). Note that content may be outdated as rules and regulations have changed.

Important Points:

04:43 "Let me recap on 2016 – I have a year-end report here. We had a rocky start in the beginning of the year…the first month was the first January in the history of the stock market…"

07:46 "Almost half of the gains happened in just a few weeks - that's why timing markets is so incredibly difficult. No one guessed this."

08:37 "Be fully diversified and make sure that you have the right risks at the right times given your specific goals…to wrap up 2016, it was a wild ride – there were a heck of a lot of different things that happened but at the end of the year if you stayed true to your investment strategy, you probably ended up with a decent year."

11:24 Start of Interview with Rachel Sheedy

Joe: (11:57) "What are some things that you're writing about that people should be aware of?"

Rachel: (12:00) "There are definitely some key points that heirs really need to be aware of that can really maximize an inherited IRA…a big key is [looking at if there] are there different rules for spousal beneficiaries of an IRA versus non-spouse beneficiaries. Spousal beneficiaries have a lot of leeway – they can essentially take the account as their own. Non-spouse beneficiaries can't do that. They've got more rules that they need to pay attention to."

12:30 "One of the key things they need to know is that they need to re-title the account…they need to re-title it as an inherited IRA and make sure that their name and the decedent's name are listed when they re-title it to make sure they know who is who – that's step number one."

Joe: (13:06) "That's right, it has to stay in the decedent's name or it could really blow up on them."

Rachel: (13:10) "That's definitely a move people should not make, they should not roll that inherited account over into their own if they're a non-spouse beneficiary. They need to re-title it as an IRA."

Joe: (13:20) "When it comes to spouses, what would you talk about in regards to keeping it in the decedent's name or rolling the decedent spouse into their own?"

Rachel: (13:32) "One of the big things is whether the surviving spouse is younger than 59 ½. If they're younger than 59 ½ and they need that money, if they keep that account as a beneficiary they can cap it without having to pay the early withdrawal penalty, and that's true for any beneficiary that's capping a traditional IRA."

Al: (16:47) "The rules are so complicated when it comes to IRAs…if you're not the spouse then you have to start taking required minimum distributions and a lot of people don't realize it even if you're 20 years old you've got to start taking a required minimum distribution."

Rachel: (17:13) "Right, that's a key point. If you want to be able to keep that IRA alive and be able to stretch it out for potentially decades, you need to start taking required distributions. You can also take out more if you wanted to, but if you take out that minimum amount you can keep that IRA going."

Al: (17:31) "That's also true for Roth IRAs, because the account owner doesn't have to take a required distribution but a non-spouse beneficiary does, although it's tax-free."

Rachel: (17:46) "Roth IRA heirs need to realize that they've got to take distributions even though the owner didn't, but the distributions will be tax-free – they are taxable income if it's a traditional IRA."

Joe: (18:00) "Rachel, this is great information. Where can our listeners get more information about you and read up on what you're currently doing?"

Rachel: (18:06) "Kiplinger.com is a great resource if you go to the retirement section our cover shows up there. You can search by different topics – IRAs, Social Security, etc."

18:19 End of Interview with Rachel Sheedy

20:02 "These are mistakes that we see those people 55 years and older making, and mistake number one is underestimating longevity."

24:05 "If you find it impossible to save, start at least small – just get the ball rolling."

33:31 "Another thing that people don't think about is the taxation of saving accounts because there are different places to save. You can save in your 401(k) or 403(b) if you have one, you can save in your trust account, savings account, you can save into a Roth IRA or a Roth provision in your 401(k) or 403(b)."

2016 Year in Review + Retirement Tips - 92 Dec 31, 2016

Joe Anderson, CFP® and Alan Clopine, CPA summarize the highs and lows of 2016 in YMYW podcast episode 92, then talk about how to automate and increase your retirement savings, how to create a retirement lifestyle game plan, and steps to take if you plan on moving in retirement. Original publish date December 31, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

01:30 "This year, if you take away any lesson from this [past] year in 2016 when it comes to your investments…is that it's very difficult for you to time the market."

04:52 "That's what investors need to do – they need to look at the long-term and not worry about the day-to-day, month-to-month, quarter-to-quarter because if you have the right investment allocation for you, then let that work."

11:23 "Evaluate your Social Security claiming strategies because we know that you can start collecting as early as 62 but there are downsides there – your full retirement age, for most of you, is 66 unless you're born after 1953 and you can take it as late as age 70. Start thinking about Social Security before you even get there because that's potentially going to be a big chunk of income for you."

15:20 "Evaluate your savings. If you have $500,000 in savings, you probably should plan not to take any more than about 4% per year. This is a rule of thumb – it's called the 4% rule… and doesn't work in all cases…in fact, if you retire younger than 66, you probably don't want to take 4% because you're probably going to run out of money sooner."

22:35 "Pay yourself first – by that, you're saving first before you're spending, and the best way to do that is if you have a 401(k) or 403(b) at your work because it comes right out of your paycheck and you never miss it. Not all of you have 401(k)s, so in that case you'll have to open your own savings account."

26:06 "Understand tax ramifications. This one is missed a lot because you may not even realize this but all the money that you've saved into your 401(k) or your 403(b) or in many cases your IRAs – [when] that money comes out it's taxed at ordinary income rates which is the same rates you're used to paying right now."

33:03 "Get serious about relocation plans. If you plan to move when you retire, find out how much you'll actually net for your house and how much it will cost to move to your new location."

34:30 "In some cases it may make sense to refinance your loan – do that while you're working because you need the income to qualify."

What's the Difference Between a TSP and a Roth IRA? - 91 Dec 17, 2016

Will a financial advisor give you an unbiased opinion? What's the difference between a TSP and a Roth IRA? Joe Anderson, CFP® and Alan Clopine, CPA answer these questions and more in YMYW podcast episode 91. Original publish date December 17, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:54 "A stretch IRA is a way for your children, when they inherit your IRA, to stretch it over their lifetime…this may go away…if it goes away, we will go back to old rules which means all money in the IRAs needs to be withdrawn within five years, which could put your kids and grandkids in much higher tax brackets."

05:17 "A Roth IRA will grow 100% tax-free. There is no required minimum distribution in a Roth IRA. If you pass with a Roth IRA, then your kids can take those dollars out tax-free. So, it grows tax-free you're your life, your spouse's life and the kids' lives. It's very powerful if you do this right."

06:54 "This is one of the most important times ever to be doing conversions; the unfortunate thing is you have to do it before December 31st for this year."

13:52 "If you're broke, you can always pull out your Roth contribution regardless of what age you are – no tax, no penalty."

15:08 - "I'm in a 30 year fixed mortgage with Wells Fargo. There have been several financial criminal incidents regarding Wells Fargo this past year. Could my mortgage be negatively affected by this as well as the interest rate hike?"

23:03 - "I recently changed my job. My new employer offers a 401(k) plan, but only after I have worked a certain number of hours. So technically, I cannot contribute towards any retirement account. So as to reduce the tax, can I contribute towards my spouse's 401(k), and max out his contributions? We file taxes jointly."

25:09 - "Will a financial advisor provide an unbiased assessment of a financial plan I already have in place? I already have an Investment Advisor connected with an insurance company who handles our investments. I would like to have an independent financial advisor who can provide an unbiased assessment of our financial plan and investments. Is it possible that an advisor would provide this service and what fee might be expected?"

33:33 - "Can I move money from a retirement account to a Roth IRA and what is the process like? Tax ramifications? Do I have to move all of it?

34:36 - "I am a government employee and have a TSP. What is the difference between that and a Roth IRA? A civilian Roth IRA and TSP?"

Tax-Saving Moves to Make Before Dec. 31st - 90 Dec 17, 2016

It's your last chance to lower your tax bill – find out some last-minute moves to save on taxes before year-end. Plus, how are your assets titled? Joe Anderson, CFP® and Alan Clopine, CPA explain why making the wrong move could cost you big time in YMYW podcast episode 90. Original publish date December 17, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

13:52 "The market magnet has begun to pull the long dormant mutual fund investors, so domestic stock funds have seen an estimate net flows of $35.8 billion in the past four weeks (Investment Company Institute)."

14:40 "History tells us that money tends to flow near market peaks…it's interesting how that tends to happen."

15:12 "Now is a really good time to take a look at your overall portfolio, and look at a rebalance strategy. There are a lot of people who set it and forget it, and then the other side of the spectrum is people who day-trade the heck out of their 401(k) plans."

20:44 "I've got five ways to lower your tax bill now, this is from Nerd Wallet and came out on December 14…when it comes to tax planning, a majority of strategies need to be accomplished by December 31st for that tax year."

23:30 "There's a special account called a donor advised fund, where you can set up the account, put your own money into it, and that money will ultimately go to charity, not necessarily this year. Here's the key – the year that you put the money into the account is the year you get the tax deduction."

24:15 "It's a great way to take a deduction when your tax bill is higher."

27:26 "Offset your capital gains with losses."

28:21 "When you tax-loss harvest, here's how you do it properly: you sell the position that's down to create that loss, and then you buy something that's very similar so you're still in the market because the market because the market may come zooming right back."

29:37 "It's important to realize how things are titled when it comes to your assets, especially your retirement assets."

29:55 "A lot of you have named your living trust as the beneficiary of that retirement account…there are pros and cons to this. There's so much misinformation on what people should do. I would say the majority of you who are married should not name your trust the beneficiary of your retirement account unless a) it's a second marriage and you want to preserve those assets if you had kids from a previous marriage; b) second of all, if you're not married and have children and those children might not be able to handle the type of wealth that is inside your retirement account."

34:59 "If I just named my spouse as the beneficiary, she could keep it in my name and take a required distribution if she wanted to, or she could roll it into her own and avoid any type of income coming out of it and being taxed on it and let it grow tax-deferred until her retirement date."

36:54 "A retirement account is completely different than say your brokerage account or checking or savings account. A retirement account has to have a required distribution from it…so be careful with how you name your beneficiaries."

37:12 "The death of the stretch IRA could happen as early as next year."

Will IRA Contributions Reduce Your Tax Burden? - 89 Dec 11, 2016

Would contributions to a traditional IRA reduce your tax burden? How do you start saving money at a young age and what are the benefits of a Roth IRA? Joe Anderson, CFP® and Alan Clopine, CPA answer your email questions in YMYW podcast episode 89. Original publish date December 11, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

02:31 - "Would contributions to our traditional IRAs reduce our tax burden? My wife and I currently have no tax write-offs and our mortgage is paid off on our home. I contribute the maximum to my 403(b), but I also have a traditional IRA and a Roth IRA, as does my wife. We have been contributing to our Roth IRAs over the years to the neglect of the traditional IRAs. I was wondering if it would make sense to start contributing to the traditional IRAs so we can start to decrease our tax burden every year. Of course, the benefit of the Roth would have tax advantages years from now when I retire. My wife and I are both in our late 40s and I have about 10 to 11 years before I think I can retire."

10:52 - "How should I start saving? I just started my first job and they don't provide 401(k)s. What should I do to prepare for life, and to start saving? I've heard a Roth IRA is the way to go. Is this something I want? Other than tax benefits, does it grow?"

15:24 - "What are the tax implications of removing part of my IRA to give to my ex-wife? My ex-wife and I had separate IRAs. We divorced in 2014, but I kept the house. I owe her money in several months as a first payment on the value of the home. What are the income tax issues I will face by removing a large portion of my IRA to hand over to her?"

19:09 - "Will a loss on our sold home off-set taxes on a 401(k) withdrawal? My wife is 65 years old and I will be turning 65 in May 2017. We are planning to move out of California to Las Vegas for good. I will have to withdraw 100% of my 401(k) to put as a down payment to purchase a home in Las Vegas. Then, we plan to sell our house in California which is paid-off. We believe that after the sale, we will have a loss. Would we be able to use that loss to reduce taxes on the 401(k) or IRA withdrawal?"

24:38 - "Will a Trump presidency reduce the tax and regulatory burdens placed on my small business? I own a small business in the New York area and have recently started to work on our 2017 financial projections. I have spoken to a number of friends, family and other small business owners about the ramifications of a Trump Presidency. Although I do not agree with many of his polices, I am hopeful that he will be able to reduce the tax and regulatory burdens of operating a business. When creating my forecast, what should assume and what should I ignore?"

27:35 - "Will I be thrown into a higher tax bracket due to a high ordinary income tax? I reach age 66 in July, full retirement age, and will continue working. I'm considering taking Social Security retirement at 66 and contributing to a 403(b) account to increase the balance. Is the entire amount, Social Security and wages, taxed as ordinary income, so that I will be thrown into a higher tax bracket? Is Social Security income counted dollar for dollar? Would it pay me to invest the max amount in my 403(b)?"

12 Ways You Could Go Broke in Retirement - 88 Dec 11, 2016

Joe Anderson, CFP® and Alan Clopine, CPA start off YMYW podcast episode 88 with a quick discussion on potential tax changes under Trump. Plus, 12 ways you could go broke in retirement and put yourself at financial risk. Original publish date December 11, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

08:28 "There are things that you want to make sure that you take a look at in regards to your overall retirement planning and tax planning, [including] Roth IRA conversions."

09:00 "Most tax planning strategies have to be finished before December 31st, so now is the season for tax planning."

10:03 "There's a lot of confusion about taxes and what may be coming in the next year with the Trump proposals and GOP proposals."

13:59 "In terms of the Trump proposal – this is also true of the GOP proposal – it would only be three tax brackets, 12%, 25% and 33%."

14:44 "Under the Trump plan, if you're married and your taxable income is below $75,000 you'd be in a 12% bracket – if it's above $75,000 then you're going to move into the 25% bracket and by the time you hit $225,000 you get to 33%."

15:00 "When you look at single taxpayers, it's the same exact thing but cut in half."

17:12 "One of the biggest things I [would consider] from a planning perspective at the end of this year would be if I'm charitably inclined."

17:46 "Charitable donations are really important and big right now because if you are in a higher tax bracket this year or next year or in the next couple of years, you want to take that deduction in a year where you get more tax benefit. There is a way to take future year contributions in the current year and that's by setting up a special account called a donor advised fund."

23:49 "The amount of money that you have in stocks versus bonds has nothing to do with your age…it all depends on when you cash flow, how much income you need and how much it needs to last."

27:08 "Multiple streams of income are better than one."

33:53 "Long-term care – that's going to be a big deal. Most of these companies are totally getting out of the business."

Is the Tax Code Changing? - 87 Dec 03, 2016

Joe Anderson, CFP® and Alan Clopine, CPA discuss a brief history of the tax code and where it might be headed in YMYW podcast episode 87. Find out some possible tax exemptions and deductions under Trump's presidency; plus, key tax strategies to take advantage of now before the tax code could change. Original publish date December 3, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

02:35 "Over the decades, Congress simply amended the tax system by adjusting and assessing new taxes in a series of 17 internal revenue acts. By 1939, the series of tax rules became the first formal internal revenue code. 15 years later was the first real tax reform….tax rates got as high as 91%."

03:51 "It was in the Fifties that the alternative minimum tax came into play, and that was really designed for the wealthiest of people."

05:50 "There's Trump's plan, and then there's the GOP plan – there are similarities but [also] some pretty big differences."

08:02 "Tax reform is not a slam dunk, even though we have a Republican president and a Republican majority in the House and Senate."

09:50 "Here's a quick nutshell on the ordinary income tax basis; this is what the proposal is. Right now we have seven brackets. They (GOP) wants to break it down to three. We have a 10%, 15%, 25%, 28%, 33%, 35% and 39.6% bracket. They want to combine the 10% and 15% bracket and call it 12%. Then they'll combine the 25% and 28% tax bracket and call it 25%. Anything over the 25% tax bracket they're calling it 33%."

11:19 "Under Trump, he would like the standard deduction to be $15,000 for an individual and $30,000 for a married couple."

15:01 "Capital gain rates right now are 0%, 15% and 20% depending on what your income levels are."

18:07 "If you are in the 10% or 15% tax bracket today, if you sell that asset there is no tax up to the top of the bracket. Here's a simple example…"

21:48 "You have to understand that things might be changing here, for the good or for the worst depending on what your overall situation is. Get an grasp on your overall situation before the end of the year to make sure you can take advantage of anything you should be taking advantage of this year and set yourself up appropriately for whichever changes may or may not happen."

26:50 "There are two main proposals on the table right now: the Trump plan and the House GOP plan. They both want to change the way we deduct itemized deductions." 27:50 "A donor advised fund is kind of like a mini private foundation..."

30:09 "One of the real benefits of the Roth conversion is for you and potentially your beneficiaries will potentially get all of that money tax-free."

33:48 "Net unrealized appreciation is another one that's probably on the chopping block. That's taking stock out of your retirement account, moving it into a brokerage account to enjoy capital gains tax."

Pros and Cons of Rolling a Retirement Account Into an IRA - 84 Nov 19, 2016

Dividend paying stocks: do you understand how they work? Also in YMYW podcast episode 84, Joe Anderson, CFP® and Alan Clopine, CPA answer your biggest financial questions, from how to claim a loss on a Roth IRA to the pros and cons of rolling over an employee retirement plan into an IRA (individual retirement account). Original publish date November 19, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:04 "Most [people] don't understand that when the dividend is paid, the stock price falls by that amount."

04:55 "It's not necessarily the best idea to focus solely on dividend paying stocks…with dividend paying stocks you're paying taxes as you go."

06:58 "It's only a matter of time that the dividend stock prices go up because of demand."

11:05 "I have a Roth IRA, open for over ten years now. I have contributed about $15,000 but lost about 80% of it due to some stocks that I invested in. Can I claim this 80% loss in my tax return?"

15:39 "I was recently told by more than one financial advisor that I should roll my employee retirement plan now that I've left the company, into an individual IRA. When I called that company to do just that, I was told by their advisor not to roll it over. He explained that I began investing in 2007/2008 when the market was low. If I were to roll over into an individual IRA today, I would be buying in when market prices are high, thus buying fewer stocks/bonds (whatever prices comprise the plan). He also said, since your plan has averaged a 5.1% gain this year, why would I want to lose that? Can someone speak to this logic for NOT rolling over?"

24:43 "Are profits from trading options (or stocks) in a non-qualified brokerage account subject to the 10.4% FICA tax?"

26:41 My wife and I are both 60 years old. We have taxable investments valued at $900,000, 401k and IRAs valued at $1,200,000, and a Roth valued at $23,000. We would like to retire in about 8 years. A co-worker said he heard that it is possible to pay no income tax in retirement, even on Social Security benefits. With my situation how is that possible?"

32:21 "A lot of people retire at 62 or 64 and are in a very low [tax] bracket, and could be doing Roth conversions all the way until age 70 1/2 and then be in a much better spot and in some cases pay little to no taxes."

Are You Ready for Retirement? Answer These Questions to Find Out - 83 Nov 19, 2016

Are you prepared for retirement? These 6 questions will help you see if you're ready in YMYW podcast episode 83. Original publish date November 19, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

Have you explored downsizing your living expenses?
Do you have a clear end game?
Where are you on your debts?
Have you "right sized" your mortgage?
Have you considered the different types of income sources available to you in retirement?
How would continuing to work at your peak earning years impact your quality of life in retirement?

Later, Joe Anderson, CFP® and Alan Clopine, CPA discuss what Trump's presidency could mean for your taxes. Plus, strategic tax moves for year-end, including tax-loss harvesting and proper asset allocation.

01:36 "Here's the first question: have you explored downsizing your living expenses?"

04:21 "I would say a lot of individuals need to reduce their living expenses."

05:09 "Do you have a clear game plan? You may have a general sense of how much money you need to retire, but you aren't truly ready to retire until you understand what it means in day to day terms."

05:21 "It's comparing your retirement number to your anticipated monthly expenses, making adjustments as needed and from there it's doing simple mathematics."

10:02 "It's [about] looking at your entire overall situation to make sure that you answer a few different questions to make sure you're doing everything appropriately."

11:00 "There could be some tax reform, there could not be…but we can at least tell you some ideas that Capitol Hill is throwing around and to make sure you're prepared…the thing you can control is how much you pay the IRS."

11:49 "I would say the people who are going to be affected if any of the changes go through is going to be small business owners, corporations and people who have a ton of money."

14:16 "There are few things that won't change, probably – one is the definition of income. Everything is still income whether it's salary, pension, rental income, interest, dividends, lottery income, gambling income, all of that is still income so that's very unlikely to change. The tax rate, however, could change but the fact of how income is being calculated is one thing that'll likely stay the same."

14:40 "Another thing is the 1099 forms which you get if you're an independent contractor. Those will still be very applicable."

16:26 "Reply to every IRS letter unless it says not to – this is common sense and it won't change under Donald Trump."

20:12 "Do not talk to the IRS if they visit you…if they come to your home or business, decline to speak to them and tell them your lawyer will call."

22:53 "If you understate your income by 25% or more – that's substantial understatement – the IRS can go back six years. Keep your tax returns forever."

24:10 "Avoid amending returns; but if you do amend, don't cherry pick…amended returns have a high audit rate, especially they request a refund."

25:46 "Be careful with a big refund. If you're getting a giant refund, the IRS is more likely to look at your tax return."

29:04 "I'm going to give you some quick tips for end of year tax planning, some real simple things you can do."

29:10 "One of them is tax-loss harvesting. What is it? Let's say you had a loss in a certain position, you sell it and buy something similar. Those losses will offset any future gain."

31:23 "Certain asset classes are in favor at certain periods of time in a cycle."

34:07 "If you don't have the right asset location, it's going to be pretty difficult for you to do tax loss harvesting. Asset location is looking at what asset classes you hold in each account (tax-deferred, taxable, tax-free)…so you need to understand the taxation of the assets you hold in each account."

36:06 "It's about being more tax-savvy in your overall scheme of things to make sure you get the best after-tax rate of return."

Money for the Rest of Us | Interview with J. David Stein- 82 Nov 12, 2016

J. David Stein, host of popular podcast "Money for the Rest of Us" joins the show to talk about, you guessed it, money. Joe Anderson, CFP® and Alan Clopine, CPA interview Stein on the state of the markets after the nomination of President-elect Trump. Original publish date November 12, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

Stein sheds light on failed market forecasts and how this past week demonstrated two points. First, you can't predict future outcomes, and second, you especially can't predict how the markets will react to those outcomes. Joe responds with the importance of ignoring short-term market volatility and instead, focus on your long-term goals when investing.

3:14 "We have two more topics, estate planning and IRAs. One of Trump's proposals is to get rid of estate taxes."

3:30 "Right now under current law if you were to pass away, your beneficiaries would receive your assets with no estate tax if your estate is less than about $5.45 million. So if your estate is $10 million and you're single, well some of that is going to be subject to an estate tax at 40% and some of it will come tax-free."

4:00 "Donald Trump would like to get rid of estate taxes altogether which is a huge saving for families that have a lot of assets, a lot of wealth, but there's a negative to that and I want to explain that."

4:10 "The last time we didn't have an estate tax was 2010, for one year, and we've had the estate tax basically since the Civil Year."

5:00 "Here's what's interesting about estate taxes is because the government doesn't want to tax an estate twice. There's an estate tax and then there's a step-up in basis for the next generation which means that any asset that you hold outside of a retirement account gets a step-up in cost basis to the value at date of death. So you bought a home for $100,000 and now it's worth $1,000,000 and your kids get the home, because it's under the exemption limit, it's as if they bought it for $1,000,000. They turn around and sell it right there and there's no gain or loss. The reason for the step-up is so you don't pay estate taxes and capital gains on the same property. Now if there is no estate tax, there may not be a step-up in basis."

6:20 "Last thing when it comes to estate planning which will affect just about everyone listening is retirement accounts.....right now there is something that's called the Stretch IRA. What that means is if your IRA goes to a non-spouse beneficiary, they have the right to stretch out the tax liability of that account for their lifetime. Once they inherit it, it's going to be taxed at ordinary income rates....right now they have the ability to stretch the tax out over their life. So it's a very favorable tax law for us individuals that inherit retirement accounts."

8:22 "What is probably going to happen, is what some experts say, first quarter next year - first 100 days, is that the [Stretch IRA] is gone."

9:46 Start of interview with J. David Stein

11:00 Joe Anderson: "Given this week, we had a lot of experts on their toes a little bit. Donald Trump is now our President...as Donald Trump was pulling ahead, you was the futures go down 700 points so everyone's thinking, oh man the market is going to crash. The week has been okay. I mean how the heck do we explain that?"

11:25 J. David Stein: "We explain that by saying, you cannot predict these one-off events. I had listeners expressing concern; if Donald Trump gets elected the market is going to crash, should I be pulling my money out? Now this was a month or two ahead of time. My response was, for one-off events you just can't predict what the reaction is going to be.

12:00 J David Stein: "Now what I teach is to adjust one's asset allocation for what I call regime changes. Where the risk of a recession is high, the risk of a 20% type decline in the stock market is high."

12:42: Joe Anderson: "We're emotional creatures and I think that's one of the biggest things from an education perspective. It's that you cannot worry about this short-term volatility. What's the goal for the money? You probably need it for your retirement over the next 10-20-30-40 years. We'll have many more presidents, we'll have many more corrections and we'll have many more crises and everything else."

14:15 J David Stein: "My insurance company had a 50% proposed increase for our health insurance. So that got me thinking, what's going on here? What is driving these dramatic increases in health insurance cost? Turns out, much of it is pharmaceutical."

15:20 Alan Clopine: "What is some of the best advice you would give to someone who is about to retire?"

15:54 J David Stein: "What I tell retirees is to find a source of income outside of investing. Have a lifestyle business or something of interest."

17:00 J David Stein: "One can't even imagine a 40-year retirement, I mean we can't comprehend what that's even like."

19:50 End of interview with J David Stein. Visit moneyfortherestofus.net to hear more from J David Stein

Taxes under President Trump - 81 Nov 12, 2016

It's been 30 years since the last tax reform, but President-elect Trump is planning for a change. Joe Anderson, CFP® and Alan Clopine, CPA take a comprehensive look into Trump's proposals in YMYW podcast episode 81 and discuss how his potential tax law changes could affect you. Original publish date November 12, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

Reduce income tax brackets from seven brackets (10-39.6%) to three (12%, 25%, 33%)
Increase standard deduction
Remove personal exemptions

03:03: "Right now we have 7 [tax brackets] and Trump is proposing to go down to three."

03:10 "A lot of people are predicting that these first 100 days that Trump is in office, we might see a lot of action."

05:30 "[Trump] is combining the 10% and 15% tax bracket to 12%."

05:48 "It all depends on what happens with the standard deduction. They are looking at doubling up the standard deduction. So for lower wage income earners that doubling up of the standard deduction will potentially have less money taxed going into that 12%, where before they might have been taxed a little bit earlier on the 10%."

06:08 "The exact numbers if you're single, you get a standard deduction right now of $6,300 and $12,600 if you're married..."

06:40 "The new numbers being proposed would be a standard deduction of $15,000 if you're single and $30,000 if you're married."

06:50 "However, right now we get an exemption of about $4,050 per person, including dependents. Trump plans to get rid of that."

08:30 "The biggest tax savings will be clearly for those who make a lot of money."

08:34 "LeBron James, he's going to save $15 million in taxes."

10:05 "The last major reform was 1986, Reagan years. That was the tax simplification act."

11:40 "How you get to your taxable income today is after your exclusions and exemptions."

13:00 "[The proposed tax changes] could hurt those with a lot of kids."

15:15 "Let's get into capital gains. If you follow what Trump is saying, capital gains is not going to change except for the net investment income tax on top of capital gains."

15:38 "The net investment income tax is not taxed on ordinary income."

15:45 "The capital gains rate, as well as what's proposed by Trump, is as a married couple, the first $75,000 of taxable income, capital gains are taxed at 0%. There is no tax, they are actually tax free."

16:16 "Then you look at, up to the 25% tax bracket into the 39.6% bracket, you're at 15% and then it's at 20%. Basically the new capital gains law, and Trump's side is the same. If you look at Paul Ryan's it's a little bit different. It's 6.5% and then it goes to 12.5% to 16.5% - those are the three different levels depending on your holding period."

16:47 "One difference with Trump is that the 20% rate will kick in at the highest bracket which he's proposing at $225,000 of taxable income and right now for a married couple that highest rate doesn't happen until about $460,000 of taxable income. So that would actually be a slight increase."

18:15 "Right now is such a key time to be thinking about year-end tax planning because the tax law may change."

23:00 "That's a great way to create tax-free income in retirement is to net your losses with your capital gain income and then you don't pay any tax on that."

The Value of a Financial Planner with Joe Saul-Sehy - 80 Nov 05, 2016

Joe Saul-Sehy, host of the top-rated personal finance podcast Stacking Benjamins joins Joe Anderson, CFP® and Big Al Clopine, CPA on Your Money, Your Wealth® podcast episode 80. Saul-Sehy talks about what investors or anyone interested in personal finance can learn from his unorthodox show focused on headlines and impressive guest perspectives. Joe and Big Al wrap up the show answering listeners personal finance questions. Original publish date November 5, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:29 - Start of Interview with Joe Saul-Sehy

03:41 - "Our goal is headlines – it's a magazine-style show…we have great discussions about current events, financial planning and making sure people have the type of great advice that's out there."

06:02 - "That's kind of how "Stacking Benjamins" was born – it allowed me to talk about money in a way where we kind of learn through play."

08:05 - "There's all this noise going on – you've got big media outlets with talking heads…everyone is talking about what you need to do now, yet you know most of the time the thing you should do is absolutely nothing. Study after study shows that the thing a great advisor brings to the table is convincing you that holding the line is the perfect thing for you to do."

12:44 - "When I was an advisor, every smart person that was a client of mine could have done my job on their own but they always went to an advisor to look over their shoulder."

15:12 - "I found that the more blunt I got, and the more I challenged people about their thinking when I disagreed with it, the more they wanted to hire me. That's probably who you should be searching for when you're looking for an advisor."

16:00 - End of Interview with Joe Saul-Sehy

19:25 - "What are some examples of a value-added tax?"

21:26 - "I am 60 years old and plan to retire at 67. I have a 403(b), a HSA, and a couple mutual funds, but I keep hearing I should start a Roth IRA. Why would I want to start a Roth on the home stretch?"

24:30 - "If you're in a low tax bracket right now, you might even want to look at Roth conversions relative to your retirement. There a lot of things we'd have to know about you to see if that's a good idea or not."

27:29 - "How much income can I make a year before my Social Security payments reduce?"

30:23 - "Can I apply to have 401(k) funds pay for a home purchase instead of an existing loan?"

7 Scary Retirement Moves to Avoid - 79 Nov 05, 2016

Are you making these mistakes that could sabotage your retirement? In episode 79 of the YMYW podcast, learn tips to avoid making costly financial mistakes with your nest egg. Original publish date November 5, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

03:15 - "You've got public pension plans and private pension plans, and sometimes they play by different rules."

06:43 - "The problem with some of these defined benefit plans and why there is $1.7 trillion underfunded is the assumptions are a little off."

09:43 - "The point is, you don't have any control over these defined benefit plans."

12:18 - "Mistake one is failing to plan for medical expenses."

17:00 - "Mistake number four is helping out adult kids."

19:03 - "When it comes to retirement, you have to pull money out of your IRAs and 401(k)s and you pay taxes on that. A lot of people don't realize that. In many cases when you've done a great job saving you're in a higher tax bracket even when you're working because of that required minimum distribution."

22:04 - "[one of] the seven scariest retirement moves…is holding most of your retirement funds in a single company stock."

24:32 - "If you do have company stock and you're heavily weighted there, before you diversify out – just make sure that you understand net unrealized appreciation."

33:11 - "Here's another scary retirement move: thinking you can actually beat the stock market."

36:20 - "No tax diversification - that means you've got all your assets in your retirement accounts…"

Propositions That May Impact Californians' Finances - 78 Oct 29, 2016

Joe Anderson, CFP® and Alan Clopine, CPA discuss some of the 2016 California propositions and how they affect your finances, in episode 78 of the YMYW podcast. Plus, what's the difference between gross income and taxable income? Original publish date October 29, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

07:02 - "Prop 13 is when you buy a home in year number two and your property taxes can only go up 2% regardless of how much the home increases in value."

09:24 - "What is the difference between gross income and taxable income?"

10:49 - "There's something called itemized deductions and exemptions. Itemized deductions would be like a home mortgage, estate taxes, property taxes and things like that."

15:26 - "For those who have the Roth provision in your 401(k) plan – you want to look at your taxable income."

17:40 - "What should I do with a lump sum pension in an IRA?"

23:52 - "I took out a personal loan of $8,000 for debt consolidation purposes with my credit union. I'm simply wondering if this loan will affect my income tax in any way. Do I report the loan on my taxes? Will it make a difference in how much my refund will be?"

25:03 - "Can I obtain a loan on a quitclaim property?"

What is the Social Security Spousal Benefit? - 77 Oct 29, 2016

What is the Social Security spousal benefit? Joe and Big Al explain in episode 77 of the YMYW podcast. Plus, how leveraging your home equity in a reverse mortgage can help you generate retirement income. Original publish date October 29, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:57 - "If you're married you have a spousal benefit, or if you were married and divorced and were married to that individual for ten years, you could potentially qualify for that spousal benefit on your ex-spouse as long as you haven't re-married."

05:23 - "If I take the spousal benefit prior to my full retirement age, I would receive a reduction in that benefit. You can take Social Security benefits as early as 62."

08:17 - "When you look at a restricted application, that goes hand in hand with your spousal benefit."

14:19 - "A lot of us are living longer and you've got to think of Social Security as maybe longevity insurance."

17:23 - "The difference between [taking your Social Security] at age 62 versus age 70 is a 76% increase."

23:03 - "[Hillary Clinton] wants to keep the tax brackets that we have right now as is except she wants to add a surtax if your adjusted gross income is over $5 million."

25:31 - "Trump would actually like to reduce our taxes; he wants to take it to three brackets – 12%, 25% and 33%. Right now our lowest bracket is 10% and our highest is 39.6%."

35:57 - "Costs of buying and selling a home only to do it again during retirement might cost you more money."

How Bond Investments Work - 76 Oct 22, 2016

In episode 76 of the YMYW podcast, Joe Anderson, CFP® and Alan Clopine, CPA answer investors' questions about bond returns, how interest rates affect bond prices, the difference between short term vs. long term bonds, and more. Original publish date October 22, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

00:44 - "Is it sensible to live on my own?"

04:06 - "Will I be penalized for a 401(k) withdrawal?"

04:59 - "I am about to turn 21 and currently in my junior year of college. I have budgeted my income so that I have a portion of it stashed in my savings every month. What sort of investments should I look into to generate more income with the excess income I receive?"

11:36 - "We should stress that we are going to talk taxes and strategies, not politics."

12:12 - "Should I invest in bonds now or after the presumed interest rate hike?"

17:05 - "The shorter term of the bond, the less risk that you're taking, hence less volatility."

18:12 - "What's the advantage of going into a short-term bond versus staying in cash?"

24:20 - "With bonds, there are two sides to this: the price and the coupon rate."

29:40 - "If you have a SIMPLE plan, can you still contribute to an IRA?"

34:16 - "Should I move my 401(k) into a money market account?"

Social Security Strategies Explained - 75 Oct 22, 2016

Joe Anderson, CFP® and Alan Clopine, CPA discuss Social Security strategies for couples claiming spousal benefits in episode 75 of the YMYW podcast, as well as strategies for single people to consider. "Big Al" closes the hour discussing the downsides of annuities. Original publish date October 22, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:25 - "Many Americans will be living solely off Social Security... people are going to need to play catch-up."

04:50 - "There are new law changes that happened with Social Security last year when it comes to restricted application and file and suspend."

06:24 - "There are two different benefits that you claim from Social Security if you're married: you can claim your own or you can claim the spousal benefit. The spousal benefit represents 50% of your spouse's benefit."

10:10 - "Just a couple of years deferring your Social Security and deferring your overall retirement means added savings and added benefits."

11:10 - "The full retirement age right now is age 66…but you can delay it as late as age 70. Every month you delay Social Security you get an increased benefit."

11:58 - "If you look at us collectively, it makes sense to wait. But if you look at us individually, it's a whole different matter. Even though we try to tell people to wait until they're 70, there are situations when you should take it early. One situation is if you're disabled."

13:38 - "If you push it (your Social Security benefit) out three years, it adds 30% more income."

21:45 - "Which annuity is better for a hands on investor?"

25:25 - "Variable annuities are very expensive…understand that variable annuities have high internal costs…and people are purchasing them for guaranteed income."

29:19 - "You have to look at the present values of those future cash flows to figure out what your internal rate of return is."

30:34 - "In most cases I would not recommend a variable annuity, I would recommend an immediate annuity. An immediate annuity means you're going to give your money to an insurance company and immediately receive income. That's the cleanest way to receive guaranteed income."

37:35 - "When it comes to retirement accounts, one of the things that is often overlooked is taxes."

Investing for Retirement Questions Answered - 74 Oct 15, 2016

In YMYW podcast episode 74, Joe Anderson, CFP® and Alan Clopine, CPA answer questions about investing for retirement, covering investment options for 403(b) accounts, tax implications of moving part of your IRA and how to avoid tax penalties when withdrawing from an IRA. Original publish date October 15, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

06:30 - "If you have a 401(k) that has a Roth option, you can put $18,000 (per year) into that Roth 401(k)."

07:51 - "If you have a 401(k) that allows you to put yet more money into the 401(k) after you max out, some plans allow you to put after-tax money into that 401(k)... here's why this could be such a good idea, particularly if you're close to retirement…"

11:11 - "How should I invest my 403(b)?"

14:38 - "Our advice is always to maximize those (employer's retirement) plans."

22:05 - "What are the tax implications of moving a portion of an IRA to open a new IRA with a different firm?"

27:17 - "With a 401(k) by law it's mandatory to withhold 20% in taxes if you do that with the 401(k)."

28:44 - "Taxes don't stop when your paycheck does – once you start tapping that retirement nest egg for your living expenses, there are all kinds of new rules and opportunities."

30:14 - "Will I be penalized for an IRA withdrawal?"

32:08 - "There is no age limit for Roth IRA conversions …so if you take money from your IRA and move it into a Roth IRA, there is no 10% penalty on that conversion. The IRS classifies that as a rollover. There would be a 10% penalty if you're under 59 ½ and you withheld taxes when you did the conversion."

32:36 - "Here's another mistake: don't withhold taxes when you do a conversion – pay the tax the following year in April when you do your taxes. If that tax bill is too high, re-characterize some, part or all of the IRA that you converted back into the IRA."

Best Time to Take Social Security Benefits - 73 Oct 15, 2016

Most women take their Social Security benefits early causing them to lose out on an increased benefit amount. Joe Anderson, CFP® and Alan Clopine, CPA discuss Social Security claiming strategies so you can get the most out of your benefit in episode 73 of the YMYW podcast. Original publish date October 15, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

10:34 - "According to Investment News, most women claim Social Security early (before full retirement age)."

12:14 - "The answer we'll always give you is to push it [your Social Security benefit] out to age 70 if you have normal life expectancy."

15:39 - "It's especially important for women because women live on average four to five years longer than men. If you can wait and take those benefits later, you'll have a lot more money to work with in retirement."

17:38 - "Social Security benefits are based on your highest 35 years of earnings."

22:30 - "When you put a tax strategy or tax plan into place with your retirement savings, you can stretch those dollars out more than you think."

26:31 - "Worst case is 15% of your Social Security income is 100% tax-free…California does not count Social Security as taxable income."

33:41 - "When you do a Roth IRA conversion… set up a separate Roth IRA."

37:51 - "When someone makes a mistake, they finally get serious about getting advice. The truth is you can save more in taxes than you think."

How to Pick the Right Target-Date Fund - 72 Oct 08, 2016

Your 401(k) plan options probably include at least one target-date fund. Joe Anderson, CFP® and Alan Clopine, CPA discuss this one-step strategy for investing for retirement in episode 72 of the YMYW podcast, then answer listeners' investing questions. Original publish date October 8, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:47 - "Unfortunately, a lot of you are not using these target-date funds correctly…first of all, a target-date fund has its own allocation."

07:53 - "There are two expenses in any investment: expense ratios and then the other cost is risk."

11:32 - "Should I withhold my taxes when purchasing a home?"

17:06 - "Will I be taxed if I don't touch the funds in a transferred IRA?"

19:21 - "We now have a monthly standing lunch n' learn; it's called Road to Retirement…it's an introduction to financial planning and the key areas you should look at. We'll go into some specific strategies when it comes to taxes, Social Security, investments."

22:02 - "What are the pros and cons of investing before/after tax dollars into a 401(k)?"

26:34 - "If we were disciplined enough to save those tax savings and invest it, we'd probably come out ahead…but most of us don't do that and we just spend whatever we have."

28:59 - "What should I do with my portion of my ex-husband's IRA?"

32:47 - "I am 51 years old and finally in a job which offers a 401(k) option…should I invest in my 401(k) or pay off my debt?"

35:58 - "Even if I don't have an [employer] match, I still want to save for retirement and I don't want to ignore it. The longer you give that money to compound, the more you're going to have. So the sooner you start saving, the better."

Tapping Into Your Home Equity With a Reverse Mortgage - 71 Oct 08, 2016

A reverse mortgage gives you the opportunity to tap into your home equity to generate retirement income. Joe Anderson, CFP and Big Al Clopine, CPA discuss whether a reverse mortgage is the right move for you in YMYW podcast episode 71. Original publish date October 8, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

01:02 - "I've got a lot [to explain] about retirement that you need to be aware of, some new tax plan strategies, pros and cons of retiring in your seventies…"

04:44 - "Part of the reason why college is so expensive is because you can borrow money so now colleges are charging more and administrators are paid more."

13:57 - "Have you ever considered how you will use your home equity in retirement? If you're going to stay in your home, will you tap into that?"

18:42 - "Home equity has not always been part of the retirement income discussion."

22:10 - "What happens is either you borrow a lump sum or a payment stream or just a line of credit that you can draw when you need it; so then what happens is you don't actually make payments – the interest that you would have normally paid just keeps accruing and adding to your loan so when your house is sold, whatever your loan is gets paid off by the equity."

24:55 - "How do you use a reverse mortgage properly?"

25:28 - "Here's a way to get cash flow: if you don't have any in your savings, you can get a home equity line on a reverse mortgage and pay for your bills that way…"

28:54 - "If all your money is sitting in traditional retirement accounts, it's 100% taxable. For a lot of you, that's where the majority of your savings are. If there were a way to get control over your taxes, the home equity loan can be a tool if you utilize it with other strategies so you pay less taxes for the rest of your life…there are a lot of ways to reduce taxes in retirement."

32:55 - "With an IRA or individual retirement account, you can buy stocks, bonds, mutual funds and ETFs. With a MyRA (my retirement account) you're buying U.S. treasuries."

Laws of Wealth | Interview with Dr. Daniel Crosby - 70 Oct 01, 2016

Joe Anderson, CFP® & Alan Clopine, CPA answer personal investing questions in episode 70 of the YMYW podcast, then welcome New York Times and USA Today bestselling author, Dr. Daniel Crosby on the show to discuss his book, The Laws of Wealth, on behavioral finance. Original publish date October 1, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

01:07 - "Will I be penalized for an excess contribution to my IRA?"

02:57 - "You may or may not be able to deduct it based on your income level and if you're in another retirement plan."

08:25 - "Will the 401(k) distribution tax be offset by the loss of my section 1231 property?"

10:26 - "That qualifies for a special tax treatment because it's a business asset, it's under code section 1231 which simply means this – if you sell the rental property at a gain, you get that lower capital gains rate."

17:15 - "Once you get to know what some of the rules are, you can actually pay a lot less in taxes."

18:43 - "Should I cash out my investments or continue to invest?"

21:21 - "You can make your own dividend, which people still don't understand. A dividend is not a coupon payment."

25:16 Start of Interview with Dr. Daniel Crosby

27:36 - "People who watch more CNBC tend to have worse results. People who are monitoring every little thing that Janet Yellen does are actually getting outperformed by people doing nothing at all, so there are a lot of ways investing runs contrary to our natural human tendencies."

30:06 - "Part of the reason why I wrote the book was to try and address the delta between what the research says are the determinants of investment returns and what most people understand them to be."

30:18 - "What do you think is the biggest bias that hurts us the most?"

33:55 - "Most people are overconfident and the people who aren't overconfident tend to be depressed – there isn't a lot of middle ground."

Will Your Taxes Get Audited? - 69 Oct 01, 2016

Joe Anderson, CFP® & Alan Clopine, CPA discuss the latest statistics on who's most likely to get audited, how often it happens, and what to do if it happens to you, in episode 69 of the YMYW podcast. Original publish date October 1, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

00:56 - "The latest stats on how often we're being audited. Who's more likely to get audited? I'll take it one step further – what do you do if you get audited?"

09:44 - "There's such a lack of planning, and that's why we do the show."

13:30 - "The oldest baby boomers are turning 70 ½; those who were born in the first half of 1946. When they turn 70 ½ that triggers a required minimum distribution (RMD)

17:42 - "The truth is, our tax rates now are lower than most times in our history..."

22:28 "A sole proprietorship goes on your tax return on what's called schedule C. You show your income, you show your deductions, and whatever the profit is – that's what you pay income taxes and self-employment taxes on."

26:22 - "In general, corporations have a lesser chance of being audited than individuals."

34:02 - "If you have to go to an audit office, here's what you do…"

8 Financial To-Dos Before Year-End - 68 Sep 24, 2016

Joe Anderson, CFP® & Alan Clopine, CPA discuss the importance of properly diversifying your 401(k) in episode 68 of the YMYW podcast. Plus, should you invest in real estate or index funds? How you can determine stock loss with a non-public company? Finally, 8 financial tasks you must do by year-end. Original publish date September 24, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

00:53 - "Why do I need to diversify my 401(k)?"

03:57 - "Bonds are there to even out the ride, to even out the overall portfolio."

05:57 - "When you take a long-term average of asset classes, more often than not emerging markets is either the top performing asset class."

11:05 - "Should I invest in real estate or index funds?"

15:35 - "If you are so inclined to do real estate, treat it as if it were a business, a company or another job because there's a lot to it. There are a lot of things that can go wrong."

21:32 - "How do you determine stock loss in a non-public company?"

26:42 - "When you have rental real estate and you sell that at a loss, that's considered business with a tenant and you can generally take an ordinary loss."

27:23 - "What is the best way to transfer or refinance through a quit claim?"

32:45 - "If you would like to go through a comprehensive retirement planning course, go to our website at purefinancial.com to learn about the course.

35:27 - "Rebalance your portfolio, and that could potentially create tax loss harvesting."

Can I Roll My Solo 401(k) to a Simple 401(k)? - 67 Sep 24, 2016

Joe Anderson, CFP® & Alan Clopine, CPA discuss some last-minute tax planning tips before year-end in episode 67 of the YMYW podcast. They also answer frequently asked financial questions, including whether you can roll your solo 401(k) to a simple 401(k). Original publish date September 24, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

04:35 - "One of the most critical elements is checking your emergency funds."

07:55 - "Take your retirement budget for a test drive and adjust your spending plan."

16:15 - "Can I convert my Individual 401(k) to a SIMPLE 401(k)?"

17:50 - "We like solo 401(k)s a little bit better, because if you're not making a lot of money you can put a lot more money into it if you want to shelter that."

22:02 - "You have to do [Roth] conversions before December 31st…you can convert any dollar amount you want to."

24:29 - "Should I be concerned about the Department of Labor scare?"

29:11 - "In some cases, the financial industry, banking industry or maybe insurance companies might feel a bit of a hit because they'd have to do things differently but I think over the long term this is good for people and the industry… in fact, this should have been done a long time ago."

30:02 - "Where should I invest my inherited money?"

35:03 - "You just have to figure out what your goal is and that will help you figure out how to invest it."

Where the Presidential Candidates Stand on Taxes - 66 Sep 17, 2016

The state of the US tax code couldn't be more uncertain. In episode 66 of the YMYW podcast, Joe Anderson, CFP® & Alan Clopine, CPA discuss the presidential candidates' opposing views on taxes and explain what tax strategies you should take advantage of now before it's too late. Joe and Al answer some listeners' questions later in the show. Original publish date September 17, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

2:37 "When you look at Clinton, her proposals for the most part are adding extra taxes for those that make a lot of money."

2:57 "Trump wants to lower the tax rates and the highest would be 33% instead of what it is right now -39.6%."

8:06 "When it comes to your own retirement, trying to conserve your own dollars and pay less taxes is huge, because if you can pay less in taxes then you can live closer to that lifestyle you want to live."

12:05 "What is the best way to leverage an old ex-employer's 401(k)?"

15:37 "At 70 ½ you have to take a required minimum distribution and if you don't, it's a 50% penalty."

15:54 "Should I retire at 66 or take a low paying job?"

16:49 "A lower-paying job will never hurt you. They will never reduce the benefit, it will help you."

20:10 "How do I report my estate distribution?"

24:55 "What should I spend first in retirement to minimize high RMDs and avoid return risk?

35:10 "There's something called smart beta. What's your take on it?"

5 Lessons to Learn from Wealthy Investors - 65 Sep 17, 2016

Joe Anderson, CFP® and Big Al Clopine, CPA discuss a two-decade study on the character traits of America's wealthy and uncover the lessons that can be learned from the millionaire next door, on episode 65 of the YMYW podcast. Original publish date September 17, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

06:41 - "Successful people often spend more time early in life focusing on bettering themselves which leads to higher income the remainder of their lives."

06:50 - "We need to keep investing in ourselves all throughout our career – things are changing so rapidly that we have to stay ahead of the curve."

13:23 - "The first check you write every single month should be to yourself – to your 401(k) or IRA. If you can automate it, all the better."

16:12 - "If you're thinking about saving money in taxes in retirement, having some of your dollars come out tax-free is key because that's what is going to keep you out of higher brackets later."

19:11 - "A lot of people don't realize they can take control over their taxes and especially in retirement."

22:00 - "If you're not maxing out your 401(k) plans and Roth IRAs, you have to get there."

24:52 - "A lot of you underestimate how much you are actually spending."

31:11 - "The fee-only community is pretty small. The really good fee-only advisors have minimums of millions of dollars."

32:07 - "Right now we have a tax system that starts at a lowest bracket of 10% and goes up to 39.6%. Hillary wants to keep that in place but an extra 4% if you have more than $5 million in income."

32:30 - "Donald Trump wants to change the brackets to be 0%, 12%, 25% and 33%."

34:35 - "Couple more things – for the alternative minimum tax, Donald Trump wants to eliminate it all together, and Hillary wants to expand it a little bit by having a 30% minimum rate for incomes over $1 million."

Best & Worst Boomers' Retirement Plans - 64 Sep 10, 2016

Joe Anderson, CFP® and Big Al Clopine, CPA discuss the good, the bad and the ugly of baby boomers' retirement plans in episode 64 of the YMYW podcast. Plus, Big Al quizzes Joe on retirement and investing questions. Original publish date September 10, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

03:30 - "There is talk about how to fix Social Security. I personally think what they'll do is they'll raise retirement age; they may raise the rates, or the amount we put in Social Security..."

08:49 - "How will you make your money work for you while reducing your risk? How will you avoid the retirement tax trap that we've been talking about that could cost you thousands of needless taxes?"

16:10 - "There are ways that you can increase your possibility of working longer; one is staying healthy, one is performing well at your current job…going back to school and learning new skills."

18:07 - "As you near retirement, tax planning becomes more important than ever, but you must use a forward-looking tax strategy."

21:42 - "True or false? If you take your Social Security benefit early, you'll lock in reduced monthly payments for life."

24:08 - "At what age do you qualify for the maximum Social Security retirement benefit? 68, 70 or 72? If you wait until age 70 you get the maximum benefit."

30:22 - "How do I avoid filing a trust return every year?"

33:27 - "I am a non- U.S. citizen living outside the U.S. and trading stocks through a U.S. internet broker. Do I have to pay taxes on the money I earn?

34:22 - "How do Roth IRAs gain interest?"

Cracking Down on the 'Mega-Roth' - 63 Sep 10, 2016

Oregon's State Senator Ron Wyden is proposing a limit on Roth IRA accounts so high-income households would face restrictions on this tax-advantaged retirement account. Would this solve anything? Joe Anderson, CFP® and Big Al Clopine, CPA discuss in episode 63 of the YMYW podcast. Later, 6 reasons to convert to a Roth IRA in your 50s and 60s. Original publish date September 10, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:50 - "People who have a retirement plan through their employer tend to have more money in retirement."

05:17 - "There's no such thing as a mega-Roth IRA."

07:12 - "Taxpayers 'are pouring dollars into incentives for retirement savings, but still far too many Americans struggle to set money aside after they cover their basics. Tax incentives for savings ought to be available to more working families and more generous to middle class.'"

11:49 - "The IRS is getting their tax money upfront when you put money into a Roth."

14:19 - "At age 70 ½, you have to take a required distribution."

23:18 - "What does a [company] match mean? It's when you put a dollar in and your company matches it."

26:50 - "If you have extended your tax return or even if you have not…and you did a Roth conversion last year, you're allowed until October 15 to re-characterize that amount."

30:53 - "If you pass away with a retirement account, the IRS wants their tax money…When you pass away, it will go to your named beneficiary…your spouse has different rules."

33:58 - "Roth IRAs do not have a required distribution to the owner but if I'm a beneficial owner it doesn't matter what type of retirement account it is…they will have to take that requirement."

Factor-Based Investing with Larry Swedroe - 62 Sep 03, 2016

Investing expert Larry Swedroe joins Joe Anderson, CFP® and Big Al Clopine, CPA to discuss his new book on factor-based investing in episode 62 of the YMYW podcast. Larry also discusses smart beta, his take on the upcoming election, and how investors should react depending on the outcome. Original publish date September 3, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:02 - "Can the IRS take the property from my trust?"

04:38 - "How much can I collect in widow's benefits?"

08:24 - "Can I re-gift a stock?"

12:35 - "A 401(k) plan will allow someone to put an amount directly into their paycheck into an account that will grow 100% tax-deferred…it's out of sight, out of mind."

15:02 - "When you start tapping your retirement nest egg, there are all types of rules – if you don't have a retirement nest egg, you have nothing to tap."

15:50 Start of Interview with Larry Swedroe

18:27 - "We identify eight factors in this book – six for stocks and two for bonds…"

20:12 - "We should have a risk-based explanation for these premiums and/or a behavioral explanation that should hold up."

20:20 - "The book goes through all of these issues for every one of the factors we recommend, and shows you the historical evidence."

22:47 - "Now there's something that's called smart beta. What's your take on that? That's just factor investing with a marketing ploy isn't it?" 24:49 "That, to me, is smart beta because it's patient trading and over time will outperform the index."

25:44 - "There is a thing that you can call smart beta, but 98 or 99 percent of what the industry calls smart beta is marketing hype."

29:19 - "Never let your political views influence your investment decisions. You should have that well thought-out investment plan that has your asset allocation. The only thing you should be doing is 1) rebalancing if necessary and 2) tax managing if the opportunity to harvest a loss is there."

33:38 - "The more you look at your portfolio, the more hazardous it potentially is to your wealth."

35:35 - "If you can't ignore the noise of the market…don't check your value."

35:55 End of Interview with Larry Swedroe

Why Save for Retirement in a 401(k)? - 61 Sep 03, 2016

Joe Anderson, CFP® and Big Al Clopine CPA answer your burning financial questions in episode 61 of the YMYW podcast, ranging from how to avoid gift taxes to why it's worth it to invest in a 401(k). Original publish date September 3, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

04:17 - "When we talk about long-term care planning, a lot of people assume we mean you have to buy insurance and that's one way to solve an issue, but not the only way."

06:20 - "Medicare covers skilled care; they don't necessarily cover custodial care. Custodial care means you're not necessarily going to get better. Skilled care can patch you up and get you out the door."

11:20 - "What type of loan should I use to buy out my sibling for inherited property?"

16:59 - "You may have a will or a trust and that will spell out how the assets will be divvied up, but a letter of instructions and meeting beforehand goes a long way."

20:24 - "Can I avoid paying gift tax? Can a grandparent gift a grandchild money for college and not have to pay a gift tax? Would the grandchild have to pay taxes on it too?"

27:55 - "I think it's really important to take advantage of the tax laws that are given to us. If you are a business owner, you can pay your child do something for your business and it becomes a deduction for you."

28:20 - "If you really understand what the rules and opportunities are, you can take some control over your taxes."

30:45 - "I recently opened an LLC and landed my first client. Is there a limitation to how much income I can make off a single client?"

31:51 - "I withdrew $8,000 from my 401(k). I have retired at 59 and have not cashed the check. If I send it back, what happens? Will I still be penalized?"

34:56 - "How much capital gains tax will I pay on a home I sold after living in it for only 13 months?"

Pension Vs. Lump Sum, 401k Rules, and the Fiduciary Standard - 60 Aug 27, 2016

Pensions in lump sum vs monthly payments, 401(k) rules, the fiduciary standard, and more as Joe Anderson, CFP® and Big Al Clopine, CPA answer listeners' investing and personal finance questions on episode 60 of the YMYW podcast. Original publish date August 27, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

02:00 - "Does the early withdrawal penalty on my IRA apply to me?"

04:40 - "Never use your IRA (individual retirement account) for anything other than retirement."

05:23 - "Do 401(k) contributions have any effect on MAGI (modified adjusted growth income)?"

08:40 - "Think of 'above-the-line' as things like income and direct expenses to that income whereas 'below-the-line' is generally personal expenses."

11:14 - "Which should I take, a monthly pension or lump sum buyout?"

16:56 - "Why should I hire a fiduciary advisor?"

20:03 - "Everybody needs a financial plan, but not everybody needs a financial planner."

23:08 - "If you can save money on taxes, your money is going to grow that much further and you can take less risk."

23:51 - "Are high-yield bonds a good investment?"

26:26 - "A high-yield bond is going to be ordinary income, and you have to pay ordinary income taxes at the highest rate."

29:50 - "Do I need to pay capital gains tax on the sale of my retail space?"

33:27 - "Which income option is best for a 70-year-old?"

35:45 - "You have to look at so many different options, you can't look at this stuff in a bubble or you might make big mistakes."

6 Ways to Reduce Your Required Minimum Distributions - 59 Aug 27, 2016

Did you know there are strategies you can use to reduce your required minimum distributions (RMDs) from your individual retirement account? In episode 56 of the YMYW podcast, find out six ways to do this so you can keep more of the money you've earned, saved, and invested through your entire working life. Original publish date August 27, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

01:45 - "Once you turn 70 ½, you have to start pulling money out of an IRA (individual retirement account). If you are 70 ½ and still working, and own less than 5% of the company, you can delay your required minimum distribution until you retire."

04:13 - "Once you turn 59 ½ you can withdraw money from your tax-deferred accounts without paying a 10% penalty."

06:54 - "A lot of people don't realize that you can do these Roth conversions even before 59 ½. You could be any age and do a conversion."

10:45 - "This is a valid way to reduce your RMDs – invest in a QLAC (quality longevity annuity contract)."

12:20 - "You can invest in your IRA up to 20% of your IRA or 401(k) or $125,000 – whichever is less."

13:04 - "Another way to lower your RMDs is to use tax-deferred accounts for bonds and bond funds, and use taxable accounts for stocks and stock funds."

16:30 - "If you invest in stocks outside of your retirement accounts and you hold a stock or stock mutual fund for at least a year and you sell it, it's subject to a special long-term capital gain rate."

23:38 - "(Another option is to) donate your required minimum distributions."

29:42 - "A lot of men and women are living into their nineties and hundreds…if you haven't really thought this through, it sort of messes up your retirement plan."

32:30 - "If we're living a lot longer, how do we adjust our retirement plans to be able to accommodate that?"

34:43 - "The old rule used to be 'save 10% of your income.' A lot of advisors are now saying 15%, that's what we say."

Financial Planning in Your 20s and Controlling Income Taxes - 58 Aug 20, 2016

Joe Anderson, CFP® and Big Al Clopine CPA answer personal finance questions about real estate investments, financial planning in your 20s, retirement, and controlling income taxes from Investopedia in episode 58 of the YMYW podcast. Original publish date August 20, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:49 - "I have 2 town home units, 9 & 10. I lived in #10 since 2006 and rented #9. I want to sell both and buy a new larger home using capital gains. I will have approximately $200,000 from #10 and $150,000 from #9 in capital gains. The new home will cost approximately $500,000. If I use these gains as down payment for a new home, do I qualify for capital gain exclusion under Taxpayer Relief Act of 1997?"

07:21 - "If you're in a divorce situation and this applies to you, you want to be careful how you do the property selling."

08:10 - "How do I become financially strong and independent at 22 years old? I have one full time job ($10,800 annually before taxes). I am 22 years old, single, and have no kids. I have no establish credit. I need to buy my first car and get an apartment or trailer before 2016 ends. Where should I start investing with $1,000? Should I put it in savings or look into binary options?"

09:38 - "Try to set aside 15% of your income at any age and keep doing that throughout your career; you'll have plenty of money when you retire."

11:39 - "My mother-in-law is in her 70's. She will live comfortably on her monthly social security check and has 1/3 of her assets in the bank. She will come into the other 2/3 when she sells her home. What do you suggest she does with the money she gets from the sale? Should she get an inflation hedge and some appreciation while being conservative at her age?"

15:52 - "A lot of times, people put investments in front of the planning, and that's where they fall into problems."

16:53 - "My father sold a piece of property that he inherited in order to pay for assisted living expenses. He passed away the year of the sale. His income was less than $15,000. Does his estate pay capital gains on the property, which gained $144,000 in value from the date of inheritance?"

24:05 - "Do I qualify for backdoor Roth IRA?" I own a 403b, 457b, and DCP account. Do these count towards the pro-rata rule?"

27:36 - "How should I manage my extraordinary tax year?"

35:40 - "Unfortunately, tapping your nest egg comes with all sorts of new rules but also opportunities if you understand the strategies."

Traditional Retirement is Dead. Now What? - 57 Aug 20, 2016

In episode 57 of the YMYW podcast, Joe Anderson, CFP® and Big Al Clopine, CPA shed light on scary statistics regarding the rise of healthcare costs and share strategies to show how listeners can protect themselves. Plus, how traditional retirement planning has changed over the years. Original publish date August 20, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

01:43 - "The typical inflation rate has been around 3% historically; we use about 3.7% to be conservative. Medically right we do about 5.7% because that's what it's been growing at."

02:55 - "If you want to get an hour full of Medicare [education] go to purefinancial.com and check out our recent webinar."

05:33 - "A lot of people don't realize that Medicare does not cover [all] long-term care stays."

9:00 - "Age 70 ½ is when you have to start taking your required minimum distribution out of your IRA and 401(k)."

15:45 - "When it comes to parents' children and how much they're spending on athletics…how much are they spending?"

25:25 - "A 25% tax bracket means you pull $100,000 out of your IRA and you pay $25,000 in tax."

29:10 - "You have to make sure you understand what's going to come to you as a guaranteed income source."

30:59 - "When we're trying to reduce taxes in retirement, probably one of the first things you have to know is your tax bracket."

Answers to Financial Questions You're Afraid to Ask - 56 Aug 13, 2016

Joe Anderson, CFP® and Big Al Clopine CPA answer frequently asked financial planning questions about divorce, tax deductions, business profits, Roth IRAs, IRA rollovers and more from Investopedia in episode 56 of the YMYW podcast. Original publish date August 13, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:32 - "I am paying off a loan for CDL (commercial driver's license) school, and wondering if it is tax deductible. Does it matter if I no longer work in the trucking industry? I'm fairly inexperienced in the area of tax deductions. I understand the interest on loans is the only part that is deductible, right?"

04:11 - "After a divorce, can assets be distributed to into an account that is not in my ex-spouses name?"

06:54 - "Can a company have an extremely high gross margin and negative operating margin at the same time?"

07:58 - "Will I have to pay capital gains tax on the sale of two different homes?"

11:20 - "Can I draw $30,000 out of my ROTH IRA and put it back within a short amount of time?

12:22 - "I am a high income worker (over $250K / year). I would like to do a Roth IRA for my wife using the back door method. What would be the benefits of a Roth IRA going forward?

16:24 - "My late wife and I bought a house 20 years ago for $450,000. My wife passed away 4 years ago to cancer, so for the last 3 years I have been filing my taxes as a widow. I'm planning to sell the house for $900,000 now. How much capital gain tax am I supposed to pay? And how much tax exemption can I get?"

20:42 - "Is a 401(k) QDRO distribution taxed twice?"

28:48 - "You can wait as late as age 70 to collect Social Security, and for many of you that's probably a really good idea because you'll get a lot more benefit doing that."

29:47 - "A lot of you are behind in your planning, but a lot of you have done a great job. Here's a way to do a little self-check; there are really five things that you need to consider when it comes to financial planning."

34:34 - "Part of being successful [in retirement] is saving on taxes because what we see is that a lot of people have the majority of their assets in retirement accounts and when you pull those dollars out, you need to pay ordinary income taxes. Here's the key: people have a lot more control over how much they pay in taxes than they might think."

3 Reasons to Ignore Presidential Candidates' Economic Promises - 55 Aug 13, 2016

Presidents can bully the Federal Reserve, but they can't set central bank policy. Joe Anderson, CFP® and Alan Clopine, CPA explain how the Fed impacts overall markets in YMYW podcast 55. They also discuss a recent article covering three reasons why you should ignore Hillary Clinton and Donald Trump's economic promises. Original publish date August 13, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

03:06 - "The president doesn't control the Federal Reserve system. The way the Fed was set up was quasi-independent and answers to Congress on monetary policy."

07:56 - "Stocks are priced based upon future predictions of what we all think the future's going to be."

12:41 - "The moment you turn 50, you can put more into your retirement plans, and then that can give you a better tax benefit via deduction because you can shelter more money via tax or have more money grow tax-free depending on what planning you're doing."

15:36 - "Any time you pull money out of a 401(k) or IRA, you have to pay income taxes – federal and state."

19:32 - "You actually have more control over how much you pay in taxes in retirement, more so than any other time in your life."

22:43 - "There are always crises, whatever they might be, but we get through them."

25:38 - "If there's a lot of inflation and everything has gone up in price, gold will probably go up in price too."

29:58 - "We are a fee-only Registered Investment Advisor; there are no commissions generated to our firm, we act as a fiduciary 100% of the time."

32:55 - "If you don't sign up for Medicare in a timely manner, then when you do sign up you have to pay more for Medicare for the rest of your life."

37:03 - "The more income that you make, the higher the premium you will have to pay."

Beware of the New 60-Day Rollover Rules - 54 Aug 07, 2016

The IRS changed the rules for IRA rollovers and not everyone is catching on. Taxpayers can only perform one 60-day IRA rollover in a 12-month period, no matter how many IRAs they own. Joe Anderson, CFP® & Alan Clopine, CPA go over this new rule and share how you can avoid getting hit with high tax bills in YMYW podcast 54. Original publish date August 6, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

01:04 - "[We made a] 7-minute video on how to plan your finances in your 20's and 30's. The sooner you start, the better off you'll be."

04:41 - "We've been talking about costly retirement mistakes, and this is a relatively new one [60 day rollover rule]. It's indirectly rolling more than one IRA in a 12-month period - it's no longer allowed."

08:11 - "It's the direct rollover where the IRS won't withhold taxes but if you select rollover, they will."

12:19 - "If you're pulling money out of your retirement account for your own purposes, whatever they might be, how do you expect your retirement accounts to grow with compound rates of return if you're taking money out?"

16:54 - "The truth is, taxes don't stop when your paycheck does – in fact, now you start tapping your retirement accounts and it comes with all new rules and opportunities."

23:19 - "There are ways around the 10% penalty, but it's not nearly as flexible as if you just wait until age 59 ½."

27:10 - "A lot of you who are taking your required minimum distribution or that are going to be taking your distributions might not need to spend it…you don't have to take that money in cash if it's in an IRA. You can take shares and put it in your brokerage account."

31:09 - "There's a potential tax-saving feature called net unrealized appreciation."

33:18 - "If you take money out of an IRA before age 59 ½, you have to pay a 10% penalty. If you don't take your required minimum distribution at 70 ½, the IRS charges you a 50% penalty."

Avoid These 6 Costly Retirement Planning Mistakes - 53 Aug 06, 2016

Joe Anderson, CFP® & Alan Clopine, CPA share common retirement mistakes they've seen for years. These mistakes that could cost you thousands, if not more, can easily be avoided if you learn how. Original publish date August 6, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:27 - "What we have found with a lot of you is that potentially you're not going to be in a lower tax bracket."

05:37 - "The people we work with have assets in retirement accounts, and in most cases they will be in the same tax bracket or higher because most people that will come into our office want to at least maintain their same lifestyle."

09:32 - "You have to put a plan together to take a look at a forward-looking strategy."

13:37 - "The first one (mistake) seems so obvious but we see it over and over again – it's not having beneficiaries on your retirement plan or IRA or having the wrong ones on your IRA."

17:34 - "As a CPA (Certified Public Accountant) for over 30 years, it does amaze me how many people fail to get the message about tax planning and strategies until they make a mistake that costs them thousands of dollars."

22:57 - "There are a lot of different requirements to name the trust as the beneficiary."

25:49 - "There is good justification for actually having a separate trust; it's called an IRA trust which has nothing to do with your living trust and you set that trust up in such a way that when you pass away, your beneficiaries become sub-trusts and you can actually have the RMD (required minimum distribution) based upon each individual beneficiary."

28:02 - "This isn't so much a mistake but an underutilized strategy because a lot of people don't really know about it. It's called net unrealized appreciation (NUA)."

30:55 - "If you keep your tax bracket low enough, you can avoid the capital gains tax so you can get those assets out tax-free to you."

34:46 - "Interest rates are at all-time lows, markets are volatile, we're living a lot longer and healthcare costs – the list goes on and on."

What You Need to Know Before Choosing a Financial Advisor - 52 Jul 30, 2016

Joe Anderson, CFP® & Alan Clopine, CPA answer frequently asked investing questions and explain key factors to look for when choosing a financial advisor on YMYW podcast 52. Should you choose a fee-only or fee-based advisor and does it matter if they follow the fiduciary standard? Find out. Original publish date July 30, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

02:27 - "I'm currently employed by two employers, which brings my yearly income to $170K. I understand my pre-tax contributions. One of my employers now offers a Roth contribution. Am I eligible to contribute to only one employer's Roth?"

04:54 - "Yes, you can contribute to both plans…can you contribute to a Roth in either or both plans? The answer is yes."

08:15 - "I just purchased a home in January 2015 and I'm now wanting to sell with a potential profit of about $60K. I am newly married as of May 2016, and would like to file Head of Household to avoid paying Capital Gains. My income alone is $44K and married we are at $74K. I would like to be sure that I am under the radar and not having to pay capital gains tax if I sell today."

09:32 - "When you're married, you can't file head of household unless you've been separated for six months and have not lived with your spouse for six months."

15:46 - "You want to work with a fiduciary 100% of the time where there are no other licenses. If they have a broker-dealer affiliation, they sell products."

20:45 - "An overwhelming percentage of retirees are very satisfied or somewhat satisfied with their financial health."

25:39 - "If you look at the average 401(k) or IRA balances of those who are 55-64…it's $100,000. If you look at all people age 55-64, the median retirement account balance is $12,000 (Source: TIAA CREF Survey)."

28:52 - "My wife and I both draw on our Social Security Insurance benefits. We are both 68 years old. We just adopted 3 grandchildren. Does this change our benefits in any way?"

30:38 - "I will be retiring in a month or so and will be about 2 years before the mandatory withdrawal. Where can I park my money so that I have the least management fees and can earn some returns?"

Is It the End for These Three Tax-Saving Strategies? - 51 Jul 30, 2016

On YMYW podcast 51, Joe Anderson, CFP® & Alan Clopine, CPA discuss three major tax-saving strategies that might be going away: the backdoor Roth IRA, net unrealized appreciation (NUA) and the stretch IRA. Learn how you can take advantage of them before it's too late. Original publish date July 30, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

04:07 - "That's why the government is trying to get rid of it (the backdoor Roth IRA), because it's a way for those who make a lot of money to do a Roth contribution kind of the backdoor way."

05:25 - "The downside of doing a conversion is that you have to pay the tax on the dollars that go into the Roth."

05:45 - "If you're under 70 ½ and you have earned income, you can contribute to a traditional IRA."

09:57 - "The most important investment, by far that you can make is an investment you make in yourself."

11:56 - "Our opinion is that if you don't have a Roth [IRA], start one now."

17:17 - "You want to make sure you understand all of these rules to truly maximize the amount of tax-free income you have in retirement."

20:32 - "We're talking about a couple different strategies that you might want to consider before the door closes on you. We talked about backdoor Roth IRAs and here's another one – net unrealized appreciation."

24:04 - "Capital gain rates – event though they're a lot cheaper than ordinary income rates, in some cases about half of ordinary income rates – the higher your capital gain, the higher the rate goes up."

31:15 - "If you pass away with a retirement account, it is completely different from any other asset that you will pass on to the next generation."

35:04 - "It's a matter of taking control over your own taxes to figure this out so not only yourself will be in a better spot or your spouse, but your kids as well with regards to your IRA."

Why You Shouldn't Time the Market - 50 Jul 23, 2016

How often do you come out on top if you try to beat the odds? Most active-fund managers fail to beat the market. Joe Anderson, CFP® and Big Al Clopine CPA share a more reliable way to invest for your future in YMYW podcast episode 50. Original publish date July 23, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

04:12 - "As the market declines, we are buying the same great companies at a discount, so now is the time to invest."

06:24 - "You want to make sure you're diversified."

07:03 - "Small companies and value companies tend to outperform large and growth companies over the long-term. But we haven't seen that the last few years. Does that mean we abandon that strategy? No, it still works if you give it enough time – that's where patience is really important."

11:01 - "We have all-time lows for the 10-year treasury…"

12:29 - "If you're a U.S. investor and getting 60% of your portfolio going to return 6% and 40% going to return 1%, you're talking about a 4% return which is half of the nominal return that the typical 60/40 portfolio has earned over the last 90 years. That's a real problem for many investors who make the mistake of relying on historical returns; they're likely to end up alive with no money."

13:20 - "Clearly there are problems in the global economy. The credit markets are telling us a different story than the stock markets. They think that economic growth is very weak and likely to continue to be very weak. The stock market, on the other hand – at least in the U.S. where stock valuations are high – one assumes then that the market thinks growth will be somewhat reasonable."

17:27 - "Bonds are not for return. They are to dampen the risk of the overall portfolio to an acceptable level…"

20:00 - "Whatever your political views are, I think it's important that you hear this message. What the academic research shows is the following: when the party you favor is in power, you earn higher returns than the people in the opposing party."

22:25 - "It's important to not let your political biases or your political views influence your [investing] decisions."

29:47 - "REITs (Real Estate Investment Trust), to me are the riskiest investments – or at least among them right now – as you can get a higher expected return by investing in a 10-year CD with a hell of a lot less risk."

32:50 - "Get realistic on your budget; take a look at your bank statement… try to figure out where that money is going, what kind of retirement lifestyle you want and then start figuring out a savings plan and start early."

Stock Markets Past and Present - 49 Jul 23, 2016

Markets are at all-time highs despite recent events. In episode 49 of the YMYW podcast, Joe and Al share smart investment strategies you can learn from past performance and give advice for investing in a bull market versus a bear market. Original publish date July 23, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

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00:00 - Intro

02:33 - "If you're invested in the stock market today, the question is: now what? Should you keep your money in the market? If you've been sitting on the sidelines sitting in cash, is it a good time to jump in?"

03:23 - "Trying to time the market is a fool's game, not to mention pretty dangerous."

05:36 - "By being fully invested when you need to be fully invested – that's the appropriate way to do it. Get invested properly and stay invested."

09:02 - "Because the stock market is volatile and you can lose money, over the long term you make a lot more money and that's the premium that you have to pay to make that extra return."

16:42 "Most of you have assets inside your 401(k) plans, IRAs, 403(b)s – that's where a bulk of your retirement assets are. Guess what? There's a tax risk there because every dollar that comes out of that plan is taxed at ordinary income rates."

21:59 "Donald Trump would like to change our tax structure with four brackets, starting at 0% and the highest bracket being 25%...the highest bracket right now is 39.6%."

27:21 "When's the last time you fully reviewed your portfolio? Are you having conversations about Social Security, taxes and Medicare?"

31:32 "No one knows when these asset classes are going to perform so you want to have some of each. People chase near term performance all the time…that's not a good formula."

Tax Tools for Intelligent Charitable Giving - 48 Jul 16, 2016

Your generosity can pay off in more ways than one: when you give a charitable gift, the IRS will forgive a tax. In episode 48 of the YMYW podcast, Joe Anderson, CFP® and Big Al Clopine, CPA share how to make tax-smart charitable donations. Original publish date July 16, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 – Intro

02:47 – "Here's what does create a tax deduction for volunteering: your mileage to and from some type of charitable event you go to…supplies you purchase directly for charity, and there are some fundraising expenses that will qualify for tax deductions. A lot of people miss those deductions. Those deductions reduce your taxable income which ultimately reduces the amount of taxes you pay."

04:36 – "If you're spending money for charitable purposes or for a specific charity, then those expenses may be tax-deductible."

07:00 – "Give appreciated stock directly to charity because the tax deduction you get is the current value of the stock on the day you donated, and you don't have to pay tax on the gain."

12:04 – "If you can get a little more sophisticated in your tax planning and combine a couple of these different strategies together, you can save money in tax and actually create more income."

14:00 – "It's called a donor-advised fund. You can actually set up a fund at a brokerage firm, it's a special account where you control the investments and then you decide which charities get what amounts…here's the key: the key is that the year you set up the account and put the money in the account – that's the year you get the tax deduction."

20:02 – "You can take money out of your IRA and give it directly to charity."

25:42 – "There's no harm in getting a tax benefit. The IRS encourages it; you just have to know what's available and what to do."

29:44 – "Once you get a better picture on how all of this looks, you'll make better decisions."

35:07 – "You have more control over taxes now than any other time in your life."

Rising Cost of Living + Medicare Q & A - 47 Jul 16, 2016

The landscape of retirement is changing. The cost of living is rising and we are living longer than ever before. In episode 47 of the YMYW podcast, Joe Anderson, CFP® and Big Al Clopine, CPA share financial tips for this new age of retirement and they welcome Medicare expert, Dr. Katy Votava to share her best ways of coping with rising Medicare premiums in 2016. Original publish date July 16, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

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00:00 - Intro

01:57 - "When you turn age 62 or 63, the income that you make is going to determine what your Medicare premiums are."

07:58 - "A lot of you are probably overspending or will overspend for your Medicare coverage and healthcare coverage so we want to talk to Dr. Katy to figure out what the solution is there to make sure you keep a little more money in your pocket."

12:11 - "We see five different expenses on the horizon that can threaten your lifestyle in retirement and that could dramatically impact anyone who's thinking about retiring over the next five years."

15:13 - "When you look at spending money in retirement you have to take a look at a lot of different factors and risks, and one of them is healthcare."

16:32 - "Having an income strategy is key and look at all the potential risks in front of you."

18:23 - Start of Interview with Dr. Katy Votava

19:22 - "People don't know when to enroll and when they don't have to. You need to get in at certain times - there are windows to get in and if you don't when you need to, then you'll have lapses and gaps in coverage and penalties down the road…enrollment periods are really key."

21:45 - "I always say it's important not to leave money on Medicare's table because if you don't tell Social Security about your change in circumstance, they won't know. But if you meet the criteria, you can do your own reporting and then most people are granted that lower premium during that current year."

23:32 - "At what age do you think people should start thinking about planning for Medicare?"

23:55- "It's a really good idea to start planning by the time you're 62."

28:10 - End of Interview with Dr. Katy Votava

29:20 - "Medicare premiums are based upon your income level because different people pay different amounts to Medicare."

34:17 - "A lot more people should be converting [to a Roth IRA] than you might think, and the reason for that is when you look at your future tax brackets in retirement, in many cases it's higher than you think because of the income you're going to be receiving."

10 Common IRA Mistakes You Don't Want to Make - 44 Jul 02, 2016

There are plenty of options when it comes to IRAs, but with plenty of options can come plenty of mistakes. In episode 44 of the YMYW podcast, learn from Joe Anderson, CFP® and Big Al Clopine, CPA how to ensure you don't blow it with your IRA. Find out how to avoid the 10 most common IRA mistakes you don't want to make. Original publish date Junly 2, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 01:09 - "Now we're in the month of July and the Baby Boomers are turning 70 ½ and having to take the required distributions. There are a lot of mistakes (made) and a lot of penalties." 07:14 - "With regards to the 401(k), if you are still working in the company and you're not more than a 5% owner of that company, you're able to delay that required beginning date to April 1st of the following year that you finally separate from service" 09:22 - "I've been a CPA for over thirty years and it does amaze me how many people fail to get the message about tax planning and the rules until they make mistakes that could cost them thousands." 12:49 - "If you're inheriting retirement accounts, you have to know what is going on. Unfortunately, they're one of the most complex tax rules when it comes to these things because of the benefits you get while you're alive." 17:13 - "If there's more than one beneficiary, let's say three children, then the inherited IRA must be split by the end of the year into separate properties, separately titled inherited IRAs in order for each beneficiary to take advantage of the stretch IRA based upon his or her own life expectancy." 21:17 - "If your spouse is significantly older than you and passes away and you keep it in the decedent spouse's name, then that IRA will have to take a required distribution as if that spouse was still alive." 27:22 - "Seeking professional advice on this stuff is so critical. If it's not with us, find someone who understands taxes in retirement and can put all of this together [for you]." 32:37 "Should I do the Roth provision [in the 401(k)] or should I do the pre-tax? Look at line 43 of your tax return because it will determine what portion of your income is taxable." 37:07 - "If you save money in taxes, your money is going to last you that much longer."

How to Solve the US Retirement Crisis - 43 Jul 02, 2016

Joe Anderson, CFP® and Big Al Clopine, CPA recap recent Brexit headlines and take a look at how the markets have reacted, in episode 43 of the YMYW podcast. Plus, is the US in a retirement crisis? If so, how can it be solved, and what can you do to achieve your financial independence? Original publish date July 2, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 02:17 - "If you think about the market, in one particular day it might go up, and the next day it could go down. So-called experts quote the same things…" 06:09 - "When markets go down, what you want to do is be more strategic. You want to look at tax-loss harvesting and rebalancing the overall portfolio. [It's a better time to do] Roth IRA conversions or distributions." 08:26 - "Achieving financial independence only comes from having a thoughtful and comprehensive financial plan. The sooner you create that plan, the sooner the independence will come." 19:39 - "When markets go down, people stop investing which is the worst thing you can do." 20:15 - "Invest regularly and periodically, like through your 401(k) for example. It's the 'pay yourself first' concept." 22:50 - "You have to make sure that you take a look at your current portfolio and make sure you understand the risks that you're taking in your overall portfolio." 27:41 - "It's not about saving 'x' amount of money, it's not about the next hot stock or some one-size-fits-all product, it's a comprehensive plan that tackles risk, income, taxes, Social Security, healthcare and so much more." 31:37 - "Many retirees underestimate future living expenses." 35:37 - "When it comes to planning for retirement, what you have now versus what you'll actually need are two totally different things."

How DOL Fiduciary Rule Change Will Impact Retirement Accounts - 42 Jun 25, 2016

The fiduciary rule change will bring some changes to the financial planning industry. In episode 42 of the YMYW podcast, find out what the new rule could mean for your savings, then learn about tax reduction strategies. Original publish date June 25, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 00:46 "If you're not familiar with a 529 plan, it's a college savings plan that you can invest after-tax dollars that will grow 100% tax-free if it's used for qualified education" 01:52 - "Other states actually offer extra benefits if you go to college in their state with their plan; California is not one of them" 07:03 - "Shouldn't all advisors offer advice in your (the client's) best interest?...That's the foundation of Pure Financial Advisors" 07:15 - "We're a Registered Investment Advisor, a fiduciary and fee-only. That means there's never a commission generated" 07:32 - "We're trying to eliminate a lot of the different conflicts in the industry" 12:43 - "Those born between January 1st and June 30th of 1946 will turn 70 ½ this year, which means you'll have to start taking your required minimum distribution" 17:35 - "If you want to do a Roth conversion, you've got to do a required distribution first" 21:34 - "You brought up a strategy that's so good that I want to go over it – it's called the backdoor Roth contribution 23:55 - "A Roth is not an investment; it's a type of retirement account. Anything that you can invest in outside of a retirement account you can also invest in a Roth IRA" 26:37 - "If you could protect your wealth from taxes, you can take on less risk…the markets are volatile, but guess what? Right now is a great time to do Roth conversions if you haven't done it already. There are tax moves you want to make right now" 32:52 - "You've got to take the noise out and understand that the fundamentals of capitalism should prevail"

What Brexit Means for Your Investments - 41 Jun 25, 2016

The markets are panicking over the Brexit vote. Original publish date June 25, 2016 (hour 1). In episode 41 of the YMYW podcast, learn what the news can mean for your investment portfolio. Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 02:08 - "Important British trading partners like India and China indicated that they were worried that the exit would create regulatory and political volatility that could harm the economies of everyone involved" 07:07 - "It's complicated; there are a lot of treaties that have been set up between countries that have to be re-negotiated" 09:37 - "I know volatile times make people a little uneasy, but that's just part of being invested in the overall global economy" 14:00 - "We can't be ultra, ultra conservative with our money because we won't keep up with inflation" 20:46 - "I'm going to talk about the seven biggest financial challenges senior citizens are facing in retirement, according to the Motley Fool" 22:28 - "We're at historically low interest rates" 26:41 - "Low interest rates are a problem, and distrust of the stock market is another one. Capitalism works over the long run" 28:18 - "When it comes to retirement, a lot of us are in a much higher tax bracket than we figured because the money coming out of our 401(k)s and IRAs are fully taxable"

Active Investing vs Passive Investing | Interview with Larry Swedroe - 40 Jun 18, 2016

Financial expert Larry Swedroe joins Joe Anderson, CFP® and Big Al Clopine, CPA, on YMYW podcast episode 40 to discuss active versus passive investing, comparing past performance numbers to illustrate which investment strategy has a more reliable outcome. Original publish date June 18, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 07:07 - "The fact of the matter is, the most successful investors understand that markets will go down and they have a strategy of what they're going to do when they go down" 08:16 - Start of Interview with Larry Swedroe 09:13 - "Let's go over real quickly this active versus passive debate" 09:36 - "He [Eugene Fama, Nobel Prize winner] defines 'active' as those who are engaged in individual stock selection and/or market timing" 12:13 - "Any decision to own any asset allocation that's different from the market is an active decision in terms of your strategy" 15:06 - "You have to be prepared to accept long periods and stay the course" 16:36 - "The market is getting smarter and it's getting harder to outperform the market itself" 17:07 - "Because the market and investors are getting more intelligent, do you think these risk premiums would ever go away? 22:34 - "Ignore the ups and downs of the market, and if anything be a rebalancer which means you're going to buy when everyone else is panic selling" 27:11 - "People's focus on dividends is a purely psychological one" 31:16 - End of Interview with Larry Swedroe 33:18 - "Another way to help with the overall volatility of the portfolio is looking at the taxation of the portfolio. You have three different pools…you want money in tax-free accounts, taxable accounts and tax-deferred accounts" 36:51 - "If you can save more money in taxes then you can take less risk in the portfolio"

All About Reverse Mortgages - 39 Jun 18, 2016

Learn simple steps for building wealth in retirement with Joe Anderson, CFP® and Big Al Clopine, CPA, in YMYW podcast episode 39. Dive into the optimal retirement withdrawal strategies for keeping your finances steady regardless of market uncertainty. Later in the hour, find out if a reverse mortgage is right for you. Original publish date June 18, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 04:23 - "In 2013 the Reverse Mortgage Stabilization Act was passed and you've probably heard a lot of bad things about reverse mortgages but a lot of those bad things have been eliminated or curtailed substantially" 05:50 - "I think the 4% rule is a very, very good tool when you're trying to understand how much money you need to accumulate to retire" 09:23 - "What we're going to talk about today is really one of the most important pillars of retirement planning; it's withdrawing money from your retirement accounts" 14:2 - "Most people's assets are in retirement accounts" 16:55 - "You need to maximize the amount of money that you are receiving from Social Security because that is going to be a large fixed income source for you that is guaranteed by the Federal government" 22:08 - "A reverse mortgage can never be reduced, frozen or cancelled, and there are no monthly loan repayment requirements" 27:43 - "As you near retirement, tax planning becomes more important than ever, but you must use a forward-thinking tax strategy" 29:59 - "To continue on our discussion about if you retire and you're trying to pull money out of your accounts and the markets goes way down, a reverse mortgage is yet another potential solution to this" 34:44 - "Reverse mortgages are tax-free"

Investing During an Election Year - 38 Jun 11, 2016

In episode 37 of the YMYW podcast, Joe Anderson, CFP® and Big Al Clopine, CPA answer questions on investing for retirement, and they share strategies for managing your portfolio during an election year. Original publish date June 11, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 06:32 - "When you inherit a retirement account, it blows up on the heirs because it's [taxed at] ordinary income for the heirs" 08:20 - "With this Bipartisan Policy Center, one of the things they want to do is get rid of the stretch IRA because it's really a pretty good deal" 12:20 - "Can an SEC licensed broker-dealer transfer your 401(k) account into an IRA without your permission?" 13:38 - "Your retirement accounts are separate properties…there's no such thing as a joint retirement account" 18:54 - "I am 47 years old. I have around $100K in a Traditional IRA. I haven't contributed anything in that account for a long time now. My current job offers a 457 and 401a plan, which I try to contribute to every paycheck. Should I transfer my Traditional IRA funds to my job's 401a or 457 account? What are the tax consequences of that transfer? Should I just keep my Traditional IRA and use it until I retire? If I transfer that money to the 457 or 401a account, should I do it in a one time transfer or installment transfers (in 5 or so years for less of a tax penalty)? 19:57 - "There's no reason to roll the IRA in the plan. I will give you an advantage.. but let's say you decide to keep it separate – there are advantages to that but probably the main one is you have more investment choices when it's in an IRA" 21:44 - "One benefit of the 457 plan is that you can take that money out at any age" 23:47 - "I have read about the presidential election cycle and am curious as to what actions I should be taking in terms of my asset allocation. When should I take those actions? How conservative would you recommend I become prior to the election? What are the most effective portfolio management strategies you would recommend in order to maintain or at least mitigate risk? I am a small time investor. I work with a small amount in an online brokerage account as well as accounts with companies such as Acorns and Betterment. I do have the ease and benefit of diversifying risk away (referring to the Modern Portfolio Theory)" 25:22 - "Here's my answer: there's no evidence that there's any sort of market swing one way or another with a presidential election. It can happen and it may happen but there's no reason to make any drastic changes in your portfolio just because of that" 29:42 - "My wife and I are 83 years old. We will sell our home for about $400,000. Will we pay capital gains tax when moving to an apartment for $2,500/month?" 31:56 - "It's June and I have not taken my RMD (required minimum distribution). Should I let the funds grow until end of the year or take average withdrawals until end of the year?" 33:34 - "I am 69 years old. My husband is 71 years old. We cannot afford the note on our home with our retirement income. We have two annuities. One for $300,000 and one for $600,000. Both are about 3-6 years old. I want to know if I cash in the $300,000 annuity, what kind of penalties and taxes will I have to pay?" 34:00 - "The first question you should ask yourself is: is the annuity in a retirement account or not? If not, every dollar you pull out is fully taxable"

New Retirement Proposals Could Be Costly for High Earners - 37 Jun 11, 2016

A 146-page report from the Bipartisan Policy Center was released last week and a lot of high earners aren't going to like it. One of the proposals is to shore up Social Security by raising the tax base. In YMYW podcast episode 37, Joe Anderson, CFP® and Big Al Clopine, CPA discuss what this report puts on the line for retirement. Original publish date June 11, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 02:39 - "This is not the first time we've seen some of these proposals; I've got to believe that some of these are going to come true at some point" 05:25 - "Probably not a lot of people realize it but at certain income limits they stop withholding Social Security" 09:13 - "If you don't have a retirement plan today, here are three reasons why you should…" 14:07 - "More and more employees are suing their employer because they don't have good choices in the 401(k) plans" 18:40 - "You have more control over paying taxes than you think, actually more so than any other time in your life" 22:37 - "As long as a marriage has lasted at least ten years, a married or divorced person can draw on his or her own benefits or the spousal benefits, whichever is higher. The recommendation is to cap the spousal benefit at a level equal to the spousal benefit received by someone married to a worker in the 75th percentile of the earning distribution" 30:37 - "The report's authors are concerned about Americans' debt, including the increasing level of mortgage debt among older people" 32:32 - "[According to the report], they're going to raise Social Security tax, they're going to raise the amount of money they're paying on Social Security…they're going to limit the deductions on mortgage" 35:00 - "If you do a little bit of tax planning, there are significant things that you can do with your money from a tax perspective to save more money for you and less for Uncle Sam"

Recreating the 401(k) & the Disappearing Pension - 36 Jun 04, 2016

The inventor of the 401(k) says he created a 'monster.' Could we see the end of the 401(k) as we know it? What about pensions? More and more employers have been quietly replacing pensions with other alternatives. In YMYW podcast episode 36, Joe Anderson, CFP® and Big Al Clopine, CPA discuss the future of retirement planning while sharing insight on what you should be doing now for your retirement. Original publish date June 4, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 3:53 - "You can put $18,000 into a 401(k) [each year] and once you hit 50 you can put $24,000 [each year] and then the employer's usually have some sort of match" 7:18 - "The good news is that 401(k) plans, especially the larger ones have significantly lowered their fees" 9:38 - "I would much rather pay a bunch of fees and costs to have the 401(k) to get the deduction or potentially the Roth 401(k) to have my money grow tax-free…versus not having the plan at all" 12:53 - "There's a lot more convoluted legalities to this (self-directed IRA); we'll just talk high-level pros and cons" 17:40 - "As a CPA for over 40 years, it does amaze me how many people fail to get the message about tax planning until they make a mistake" 22:38 - "If you are divorced, can you collect a benefit based upon your ex-spouse's earning history?" 33:17 - "We're giving you a workaround (for making a budget), which is pay yourself first and spend the difference. If you don't pay yourself first…you'll find a way to spend it" 33:56 - "You do need to do a little bit of planning to figure out how much you can spend each month, and then have that come out as an automatic withdrawal from your spending account so you don't spend any more than that" 35:27 - "Taxes don't stop when your paycheck does"

Mistakes to Avoid in Managing Assets for Estates - 35 Jun 04, 2016

Nicole Newman, Attorney at Law joins Joe Anderson, CFP® and Big Al Clopine, CPA on YMYW podcast episode 35 to discuss the most important estate planning mistakes people need to avoid. Later in the hour, they dive into Social Security, investments and taxes. Does your Social Security strategy line up with your retirement plan? Original publish date June 4, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

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Learn more from Nicole Newman: 10 Gruesome Estate Planning Mistakes to Avoid

00:00 - Intro 02:47 - "We have seen Social Security benefits reach a million dollars [before]" 06:35 - "When you get really good rates of return, there are risks involved no matter what the investment vehicle is" 08:40 - "Cash flow is king when it comes to retirement. Do you have a strategy and plan in place to make sure that you can provide the income that you need?" 10:00 - Start of interview with Nicole Newman 11:52 - "What happens if you fail to plan for your death is that each state has their own back-up plan for you.." 12:59 - "They tend to interchange the terms will and trust all the time…actually that's mistake number two in my seminar" 13:39 - "A will does NOT avoid probate…that's a very common misconception" 14:18 - "Here in California probate is very lengthy, so it usually takes about 12 to 18 months as long as there are no problems…if there are problems then it can turn into years very quickly; whereas other states' probate can be very simple and very quick" 17:47 - "We see this quite often, where we'll see children from a prior marriage cut out simply because of the lack of planning…when you have a blended family you definitely want to have a living trust" 19:22 - End of interview with Nicole Newman 24:41 - "Each year that you wait after your full retirement age, Social Security will guarantee an 8% delayed credit to the benefit, plus you also get the cost of living benefit" 28:48 - "In retirement you have more control [over your taxes] than any other time in your life" 36:29 - "There are a lot of other things that you can do; you could push out your retirement a couple years or you could look at some tax planning strategies that will carry out your dollar a little longer…making sure you have the right portfolio set up to give you the income that you need"

Is 'Sell in May, Go Away' Good Advice? - 34 May 28, 2016

Is the well-known trading adage, "sell in May and go away" actually good advice? Joe Anderson, CFP® and Big Al Clopine, CPA discuss this in YMYW podcast episode 34 before diving into retirement planning, sharing common IRA and Roth misconceptions and beneficiary blunders that could cost your family thousands. Original publish date May 28, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro 02:26 - "You can contribute up to $5,500 (to an IRA); if you're over 50 you get a $1,000 catch-up so $6,500" 04:01 - "If you're in a low tax bracket you might not get that much benefit. You might as well do a Roth contribution so you forgo the tax benefit today but all future income, growth and principal are tax-free later. Here's the caveat – you need earned income" 04:29 - "Earned income has to be salary or positive profits from your self-employment business" 09:01 - "If you don't have an IRA already established and you try to do a direct rollover, you're going to find yourself with some problems" 14:59 - "Did you know that you can use your spouse's earned income if you're not working to do a Roth or IRA contribution?" 16:03 - "A couple of other basics when it comes to the Roth: there is no required minimum distribution (RMD)" 23:08 - "These are retirement accounts. They're for retirement; they shouldn't really be used for other things" 28:52 - "We're talking about IRAs, some mistakes you might be making with the overall retirement accounts; we talked about the basics – how much you can contribute, AGI limitations, penalties, RMDS. But one that people forget about is the beneficiary designation" 33:10 - "We encourage our clients and I'll encourage you guys as well to be looking at your beneficiary statements on all IRAs, 401(k)s, 403(b)s every few years; make sure they're up to date" 36:16 - "There is such thing as an IRA trust"

How Stocks Perform in an Election Year - 33 May 28, 2016

The 2016 election race has already offered plenty of surprises, but what could it mean for the economy? Joe Anderson, CFP® and Big Al Clopine, CPA share what they think, then move on to discuss Americans' top regrets in retirement. Are you saving enough money for emergencies? Is your credit card debt hindering your finances? Are you taking enough risk in your financial portfolio? Find out what you can do to improve your finances. Original publish date May 28, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

05:15 - "We tend to sell our positions when they go down because we are fearful…and then we buy back in when the market does well"

10:40 - "Here's an interesting statistic I got from Market Watch: since 1950, a 60/40 bond portfolio…hasn't had a loss in a five-year period…any five-year period"

17:54 - "Presidential election year or not, it doesn't really matter. You need to get the right investments for you and stay invested. Rebalance when you need to"

22:53 - "According to this article on U.S. News, they're saying that people over age 50 spend an average of 40-45% of their household budget on housing and housing items"

27:25 - "We talk about being diversified with investments but you also have to be diversified with your taxes"

Investing Q & A + Tax Quiz - 32 May 21, 2016

Joe Anderson CFP® and Big Al Clopine, CPA answer real life investment questions for retirees and pre-retirees. Plus, 10 retirement statistics that might scare you. Joe and Al close the hour with a quiz on taxes - how will you fare? Original publish date May 21, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

01:56 - "GoBankingRates.com finds that more than half of Americans have less than $10,000 saved for retirement"

04:55 - "Can I roll over an old 401(k) to fund my child's 529 plan?"

09:05 - "Can I use tax money owed from my IRA to pay credit card debt?"

12:47 - "We want to sell my parents' house and my sister just wants to take over my payments. Do we get any of the money we've already put into the house back?"

18:17 - "If you know a few simple [tax] strategies you can save a lot of taxes in retirement"

19:39 - "Could I convert my IRA to a Roth and use the interest tax credit to reduce my tax liability on a transfer?"

25:28 - "What can we do if my ex-husband is trying to get his 401(k) to cash out from his previous employer but they are refusing to give it to him?"

30:57 - "If you ever get a call from the IRS, hang up and if you think it's valid, then call them yourself to make sure you're actually talking to the IRS"

36:14 - "I hear this all the time – the rich don't pay any taxes – I can tell you, I've been preparing returns for 30 years, that is not true. The rich pay a lot of taxes"

15 Mistakes People Make in Retirement - 31 May 21, 2016

Joe and Big Al cover 15 mistakes even the smartest people make in retirement, courtesy of Go Banking Rates, in YMYW podcast episode 31. These mistakes include: claiming Social Security too early, being too conservative or aggressive with investments and failing to take your required minimum distributions (RMDs). Find out how to make your golden years the most successful they can be. Original publish date May 21, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

05:17 - "When you look at the taxation of your retirement income… there are some significant things you can do"

09:40 - "We're talking about mistakes people are making and one of them is not necessarily taking a look at their home when they sell it and understanding the tax law"

11:34 - "If all of your money is in a retirement account, IRA, 401(k), 403(b)s and the like, all of that is going to be taxed at ordinary income rates – the highest of rates. You want to prioritize where you're going to be pulling your money from in retirement"

13:57 - "Another big mistake that people make is that a lot of you are taking Social Security maybe a little too early"

21:14 - "Unfortunately we don't take enough time to do upfront planning"

25:49 - "The truth is, taxes don't stop when your paycheck does; when you start tapping your retirement nest egg it comes with all sorts of new rules and opportunities"

Retirement Realities vs Retirement Myths - 30 May 14, 2016

Retirement isn't what it was when your parents left the workforce. In fact, it may not be what it was even a decade ago. In YMYW podcast episode 30, Joe Anderson & Al Clopine, dive into the realities of retirement as they shed light on 10 mistakes to avoid when achieving your retirement goals. They close the hour providing 11 fast facts about Roth IRAs. Original publish date May 14, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

05:59 - "You want to have an advisor that can really understand cash flow needs throughout retirement, taxes and how the investments all fit together"

10:14 - "We are living longer, and here are the stats – they're changing rapidly"

17:58 - "Don't fall for these three retirement myths"

19:44 - "Here's probably the biggest myth: you won't have to pay taxes [in retirement]"

21:25 - "Social Security income is tax-free in the state of California"

25:58 - "There are lots of ways to create tax-free income to keep less of your Social Security taxable, but you have to understand what those strategies are"

30:21 - "A spousal IRA works like this: let's say your spouse is working and you're not working or vice versa; as long as there's earned income, the non-working spouse can still contribute to a retirement account"

9 Ways to Build Your Wealth in Your 50's - 29 May 14, 2016

If you're in your 50's, retirement is probably right around the corner. During this time it's critical to make the right financial decisions to achieve your retirement goals. In episode 29 of the YMYW podcast, Joe Anderson, CFP® and Big Al Clopine, CPA break down 9 financial tips to help you enjoy a rich retirement, whether you're a late bloomer or you've been saving up money for years. Find out how to build wealth now and for the future. Original publish date May 14, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

05:27 - "When you turn 70 ½ and you have retirement accounts, there's a mandate that you have to take a certain percentage out of the account per year, and each year as you age that percent increases…when you have multiple accounts you have to be careful"

08:55 - "A Roth IRA does not have a required distribution; but if you have a Roth 401(k), the Roth 401(k) does have a required distribution"

11:28 - "There is no age limit for a Roth IRA contribution"

13:30 - "Income limits could prevent you from contributing so here are the new rules for 2016" 20:01 "What's happening now, especially with a lot of Baby Boomers is a lot of them are working longer than they want to work…in other cases people are having to reduce their lifestyle"

22:19 - "Here are some quick steps to build wealth in your 50's"

28:38 - "22 percent are very confident they will have enough money in retirement according to the Employee Benefit Research Institute's annual retirement confidence survey"

Retirement Errors That Will Crush Your Investment Gains - 28 May 07, 2016

Learm how you can protect yourself from one of America's fastest growing crimes – identity theft. Plus, what's it going to cost you to retire? In episode 28 of the YMYW podcast, Joe and Al share three retirement errors that will crush your investment gains. Original publish date May 7, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

1:17 - "Identity theft is a real issue; we talk about it a lot on this show, especially when it comes to taxes and people filing fraudulent tax returns"

2:17 - "We focus on consumer education…educating the public on various issues related to identity crime and how to protect themselves"

4:50 - "Limit the amount of personal identifying documents that you carry with you every day"

5:30 - "Regularly monitor your bank statements and you should be checking your credit report several times a year…also shred your mail"

6:32 - "Get yourself off the list for pre-approved offers"

7:18 - "Secure your phone, tablet, your computer and understand all those pieces of hardware have lots of sensitive information about you"

11:28 - Identity Theft Resource Center contact info

21:42 - "If you're married, there are certain marital benefits – first of all, if you file a joint tax return and be in a lower tax bracket. For Social Security, if one spouse passes then you get to keep the higher of the benefits"

32:07 - "There are many mistakes you can make as a retirement investor. I want to focus on three retirement errors investors make all the time"

34:27 - "It's crucial to save for retirement but equally important to enter retirement debt-free"

Maximizing Social Security Benefits Under New Rules - 27 May 07, 2016

Social Security changes are now in effect. In episode 27 of the YMYW podcast, Joe Anderson, CFP® and Big Al Clopine, CPA explain the best ways to maximize your benefit despite two major claiming strategies now eliminated. Listeners are also faced with the realities of retirement, as Joe and Al debunk common retirement and Social Security myths. Original publish date May 7, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

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00:00 - Intro

06:07 - "The (2016) retirement confidence survey (by Employee Benefits Research Institute) reports that almost half- 47% of workers surveyed – think they'll need to save at least $500,000 for a comfortable retirement"

11:24 - "At certain income levels, your Social Security income is tax-free"

15:44 - "Even if you're currently retired, you have to look at what tax consequences are on the income you are producing"

16:55 - "That's what Social Security is giving you, it's a delayed retirement credit of 8% per year, each year that you delay"

22:48 - "We're living longer so it makes sense to push the retirement age out; that's just pure logic"

27:34 - "We're going to talk about dealing with fear and uncertainty in retirement and here are six ways to deal with it"

Creating Tax-Free Income in Retirement - 22 Apr 16, 2016

Big Al Clopine, CPA and Joe Anderson, CFP® share more ways to create tax-free income and savings in retirement in episode 22 of the YMYW podcast. Find out how the recent Social Security changes in 2016 affect your taxes and what other taxes in retirement you might encounter. Original publish date April 16, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

01:14 "Now that you have your claiming strategy dialed in, have you thought about what the taxation will be on your Social Security? It will depend on a few things"

05:03 "You want to be looking at Roth conversions because if you can prepay some taxes while you're in lower or even similar tax brackets, you can stay out of higher taxation later"

09:02 "It's all about putting yourself in the driver's seat when it comes to taxes. I would say the majority of folks don't give it much thought; at this time of the year they just pay their taxes and think that's the best they can do"

14:40 "Did you know that if you go on vacation and do Airbnb, as long as the visitors stays [at your house] less than 14 days, it's tax-free income"

15:01 "Here are your choices [for tax-free states to live in]: Nevada, Washington, Texas, Wyoming, South Dakota, Tennessee, New Hampshire and Alaska"

20:03 "Here's a survey done by the American Institute of Certified Public Accountants…they asked folks about the next president and asked what the priority should be from an economic standpoint"

24:20 "The more income you make the higher your [Medicare] premiums are…so could they do something with that for Social Security?"

33:06 "Roth conversions offer a possible solution to help clients manage taxes in retirement"

How to Save on Taxes in Retirement - 21 Apr 16, 2016

The best time to start planning for next year's tax season is at the end of this year's tax season. In episode 21 of the YMYW podcast, Joe Anderson, CFP® and Big Al Clopine, CPA tell you how to avoid tax surprises and reduce your taxes in retirement. Original publish date April 16, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed.

00:00 - Intro

03:22 "The reason we talk taxes right at the end of tax season is because this is when you're thinking about it and the best time to make a change is right now for 2016 because most strategies that are available to you take time to implement"

05:33 "The truth is, you have more control over how much you pay in taxes in retirement than any other time in your life"

07:29 "You could be generating hundreds of thousands of dollars of income and pay very little tax on your Social Security depending on how that income is classified"

12:19 "We've seen people who have money outside of retirement accounts that pay very little tax, sometimes none because of tax loss harvesting and municipal bond income"

19:02 "Our firm has always been a fiduciary, we are a fee-only Registered Investment Advisor (RIA) and never accept commissions of any kind"

26:37 "When you take money out of a 401(k) or IRA, you have to pay taxes on it, and a lot of people don't realize that"

35:49 "You can actually do the Section 121 Exclusion and the 1031 Exchange on the same property"

4 Retirement Plan Loopholes That Could Close Soon - 20 Apr 09, 2016

Original publish date April 9, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed. In episode 20 of the YMYW podcast, Big Al and Joe share four retirement account loopholes that could close soon. Plus, what you need to know about the recent changes to Social Security and how that could have a huge impact on your retirement.

00:00 - Intro

01:54 - "You don't have to sell your stocks when you do a required distribution"

03:53 - "If you have saved a lot of money in your retirement accounts, you have to start pulling it out starting at age 70 ½"

06:44 - "We think Roth IRA planning is significant, because if you can control the amount of money that is tax-deferred that will come out as ordinary income versus tax-deferred that will come out tax-free, those are two different animals"

11:14 - "The government is changing the rules on how you can claim your [Social Security] benefits, and the deadline is just around the corner"

14:10 - "If you turned 62 years old by 12/31/16, you still qualify to take a restricted application"

21:24 - "The longer you wait [to retire], the better off you'll be from an income standpoint"

26:19 - "You have more control over how much you pay in taxes in retirement than any other time in your life"

34:53 - "Taxes don't stop when your paycheck does, and a lot of people don't realize that"

Frequently Asked Investing Questions - 19 Apr 09, 2016

Original publish date April 9, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed. In episode 19 of the YMYW podcast, Joe and Big Al tackle some of the biggest questions about investing, including "Should I wait to buy a home until after the election?" and "If I'm a first time investor, should I invest with cash or margin?" Plus, Joe and Al look at the seven successful habits to help you reach financial independence, according to U.S. News & World Report.

02:46 - "With our firm, we act as a fiduciary 100% of the time"

07:08 - "April 18th is tax day this year"

13:01 - "California real estate is appreciated quite a bit more than the United States given the last 30, 40, 50 years"

19:51 - "Can I deduct my IRA contribution if I don't have an employer plan?"

27:49 - "The truth is you can save more in taxes than you think, but you must use a forward-looking tax-efficient strategy"

34:57 - "Paying yourself first means paying yourself before paying your bills…as our paycheck grows we tend to spend more"

Most Commonly Asked Questions About Taxes, IRAs and 401k - 17 Apr 02, 2016

Original publish date April 2, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed. Episode 17 of the YMYW podcast, Big Al and Joe answer the most commonly asked questions about taxes, IRAs, 401ks and Roth IRAs. Plus, their favorite tax strategies.

00:00 - Intro

04:02 - "If you're married and one spouse is still working, you can still contribute to a Roth or IRA because of the non-working spouse election"

07:45 - "If I'm full retirement age and I'm still working, I think it makes more sense to delay to get the 8% delayed retirement credit"

10:28 - "What is the optimal long-term investment vehicle when someone has maxed out all tax-advantaged accounts?"

18:16 - "Let's say you have an IRA and you have stocks inside this IRA, and some of these stocks have gone down in value. Should you take your RMD from these stocks?"

21:29 - "An RMD is a required minimum distribution that you have to pull out of a retirement account if it's an IRA if you're over 70 ½"

25:38 - "When markets are down, Roth IRA conversions are a phenomenal strategy"

29:59 - "Your upfront contributions to a Roth IRA are tax deductible – true or false? False. They are not tax-deductible, they grow 100% tax-free though"

33:45 - "There is no age limit for contributing to a Roth as long as you or spouse have earned income to contribute"

37:25 - "The bottom line is if you're not contributing money to a Roth IRA or converting money to a Roth IRA, you've got to be looking at this because tax rates may be going up in the future"

Top Tax Moves The Rich Use to Stay Rich - 15 Apr 02, 2016

Original publish date April 2, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed. In episode 15 of the YMYW podcast. Joe and Big Al share the top five most costly retirement mistakes you could be making. Plus, don't miss these top tax tips the wealthy use to stay rich.

00:00 - Intro

06:18 - "If you make a big financial mistake at this stage in your life, you may never recover and we've seen huge mistakes. You'll be paying for it the rest of your life"

11:06 - "Here are some costly investment mistakes"

15:05 - "The reason I think they're so emotional [with their investments] is because they don't have that well thought-out financial plan or financial strategy"

19:52 - "[Have] the right asset allocations; some of you might have a portfolio that is suited for a 40-year old when you are in your 60's, and some of you might not be taking on enough risk"

24:10 - "If you think about where your retirement assets are located, probably most of them are located in IRAs, 401(k)s and 403(b)s. Guess what? When you take the money out of those plans, you have to pay income taxes on it."

31:25 - "If you think about taxes and tax planning during the year, you could actually make a pretty big difference in your tax liability"

34:27 - "We're a financial planning firm that focuses on all areas of financial planning, but taxes are a big deal because we manage a lot of money... and we want to make sure we give them the highest after-tax return possible"

Money Mistakes and How to Fix Them - 14 Mar 26, 2016

Original publish date March 26, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed. Episode 14 of the YMYW podcast is about money and our behavior: the biggest mistakes you could be making and how to fix them. Big Al also covers some tax strategies to consider as you approach retirement.

00:00 - Intro

01:08 - "One mistake is this: when you are investing your money, you might be confusing results with activity"

04:47 - "You have to look at conventional wisdom and throw it out the window when it comes to your overall investment strategy"

09:20 - "These are seven ways my expenses will change in retirement"

12:19 - "The cost of healthcare tends to increase significantly in retirement; average annual expenditures for healthcare jump from $3900 among workers age 50-64 to $5000 for retirees age 65-79" (Source: U.S. News)

21:18 - "The idea is to get away from commission-only [advice] which is what most of the industry still is"

36:49 - "I've been a CPA for over 30 years, and it amazes me how many people don't realize what strategies are out there, and they end up making poor decisions, big mistakes and they don't realize how important tax planning is until they do make the mistake that can cost them hundreds of thousands of dollars in taxes"

Top Retirement Myths That Can Ruin Your Financial Plan - 13 Mar 26, 2016

Original publish date: March 26, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed. Episode 13 of the YMYW podcast is about retirement myths that can ruin retirees' plans. Find out why Baby Boomers won't be able to have a retirement like their parents.

00:00 - Intro

02:07 "40% of unmarried women have saved less than $1,000 [for retirement], according to a 2016 Retirement Confidence survey by Employee Benefits Research Institute"

05:55 "The opportunity is that we are living a lot longer and we get to enjoy our golden years longer which is great, but we also have to have a plan to cover it because it's not just Social Security anymore"

12:58 "Al and I have seen people who have millions of dollars and they blow through their money very, very quickly. Then we see people who have less than $100,000 and live a very comfortable retirement. It's about figuring out what retirement looks like to you"

18:09 "The Bureau of Labor Statistics predicts that more than a fifth of boomers 65 and older will be holding on to a job in 2024. When their parents were the same age in 1994, only a tenth were still employed"

27:12 "A lot of people are shocked when they find out how different types of retirement income are taxed, and I want to go through the six most common types of retirement income and how they're taxed"

32:12 "For those who have been listening to our show and have been doing Roth IRA contributions and Roth conversions, you'll be very happy to know that as you take money out of those accounts, it's all tax-free—100% tax-free"

Risks in Retirement vs. in Your 20s - 12 Mar 19, 2016

Original publish date March 19, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed. In episode 12 of the YMYW podcast, Joe and Al talk retirement risk. While risk can come in all shapes and forms, it's important to avoid making these risks when planning to maintain your lifestyle in retirement. Al closes off the discussion by discussing a fun personality quiz by Mashable you can take to figure out what your retirement passion project will consist of.

00:00 - Intro

01:01 "When you're in your 20's and 30's, you've got a long run in front of you and can afford to take on risk, but if you're retired or close to retiring, risk is enemy number one. Taking on too much risk at that stage of the game can be devastating because you may not be able to recover"

06:56 "You better make sure that you have a plan to make your money last into your 90's"

13:21 "If you're saving 4% this year, save 5% next year, 6% the year after and get yourself to the point where you're saving between 10% and 15%, and if you're older and getting closer to retirement and you're behind, there's no time to waste—you have to save as much as possible right now"

13:42 "Forbes had thirteen financial risks you can avoid; here are some examples"

18:04 "Unfortunately, taxes are likely going up in the future"

22:36 "One of the biggest misconceptions in retirement planning today is that you will be in a lower tax bracket in retirement"

29:10 "One in three Americans have zero dollars saved for retirement" (Source: Bankrate.com)

How to Avoid the Risk of Retirement Crisis - 11 Mar 19, 2016

Original publish date March 19, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed. In episode 11 of the YMYW podcast, Joe and Al discuss how retirement planning can help you avoid risks and keep you out of a retirement savings crisis. Find out if you should take advantage of these soon-to-disappear Social Security claiming strategies.

03:56 "Waiting for triggers in the overall market for you to make decisions financially is not the right move; you have to get your strategy in place now"

08:37 "Things have got to change and you really need to put things in perspective and start planning as soon as you possibly can"

10:32 "When it comes to these new [Social Security] rules, you have to act now. Let me explain what they are—there are two benefits that are going away"

13:14 "If you turned 62 years of age by 12/31/15, you still qualify to take that restricted application. You can take it on an ex-spouse as long as you were married to that ex-spouse for ten years, or if you are currently married"

18:06 "File and suspend is going away and you've got until April 28 to do this"

22:41 ""If you're married, it's a really good idea for the spouse who has the highest benefit to wait as long as they can, hopefully to age 70. Why is that? First of all, while you're both living, you'll enjoy that higher benefit, and when one of you passes (let's say the higher wage earner passes), then the spouse will get the survivor benefit which is equal to the same as the spouse that passed away"

34:18 "Tapping your retirement nest egg comes with all sorts of new rules and opportunities. Instead of contributing to tax-deferred accounts that reduce your taxes, you'll start tapping those savings for income and paying taxes at your regular rate—unless you're tapping into a Roth IRA, which we want you to be thinking about right now"

How Retirement Smart Are You? - 10 Mar 12, 2016

In episode 10 of the YMYW podcast, Big Al tests your retirement planning smarts by asking Joe and the listeners important retirement questions. How do you stack up? Original publish date March 12, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed.

2:08 "The government must systematically devalue our currency so they can pay it back on cheaper dollars"

8:14 "Index funds tend to have very low expense ratios"

11:51 "Which of these pose a big threat to your retirement security? Inflation, investment ups and downs, outliving your financial resources or all of the above?"

16:02 "You want to stay liquid in your strategy because things will change in your life, in the stock market and in the tax code"

20:30 "You don't have to pay taxes on money you take out of a Roth IRA if you qualify"

25:18 "You have more control over how much you pay in taxes in retirement than any other time in your life if you just understand the strategies"

How to Take Advantage of Upcoming Social Security Changes - 9 Mar 12, 2016

Original publish date March 12, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed. In episode 9 of YMYW podcast, Joe and Big Al talk Social Security! Big changes are coming up fast, listen to find out what you need to do right now to take advantage before it's too late.

02:03 "Sanders would take tax capital gains rates at ordinary income and eliminate opportunities under current law for avoiding the tax through gifts and requests for appreciated property"

08:01 "We did a Social Security Webinar; if you want to check that out, go to our website"

11:44 "In just a matter of weeks, those little known [Social Security] claiming strategies are coming to a screeching halt. The government is changing the rules on how you can claim your benefits, and the deadline is just around the corner. For those who are eligible, you have a very short window to take action"

17:09 "April 28th [2016] is the deadline for you to file for your benefit and suspend them"

24:16 "If you're married, it's a really good idea for the spouse who has the highest benefit to wait as long as they can, hopefully to age 70. Why is that? First of all, while you're both living, you'll enjoy that higher benefit, and when one of you passes (let's say the higher wage earner passes), then the spouse will get the survivor benefit which is equal to the same as the spouse that passed away"

27:52 "If you do the appropriate planning, if you understand how this works, you could save significant dollars on your taxes"

34:03 "What is not included in provisional income is your Roth IRA distributions"

35:49 "Taxes don't stop when your paycheck does…as you near retirement, tax planning becomes more important than ever"

Retirement Account Myths, Misconceptions and Mistakes Part 2 - 8 Mar 05, 2016

Original publish date March 5, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed. In episode 8 of YMYW podcast, the retirement account show continues with strategies for self-employed individuals, horror stories of working with non-fiduciary advisors, and the top IRS scams you absolutely must know about.

Retirement Account Myths, Misconceptions and Mistakes Part 1 - 7 Mar 05, 2016

Original publish date March 5, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed. Episode 7 of YMYW is dedicated to retirement accounts and everyone who has one! Joe and Big Al share the biggest myths, misconceptions, and mistakes people make. Plus, new laws and proposals that could have a big impact on your retirement.

The Incredible Shrinking Alpha with Larry Swedroe - 6 Feb 27, 2016

Original publish date February 27, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed. In episode 6 of YMYW, Larry Swedroe joins the show to discuss what recency bias is and why you should avoid it. Joe and Al ask Larry what the key to successful investing is, and Larry talks about his books The Incredible Shrinking Alpha and Think, Act and Invest like Warren Buffett.

2:12 "The conventional wisdom goes like this: take distributions first from taxable accounts such as your brokerage accounts, then from tax-deferred accounts like your IRAs and 401(k)s…that is the rule of thumb for most advisory firms"

8:05 Interview with Larry Swedroe

9:14 "What investors tend to do, as we know, is they tend to buy after periods of strong performance which means they're buying when prices are high and then they tend to sell after periods of poor performance, which means valuations are relatively low and expected returns are not high"

10:01 "Research shows, shockingly, that individual investors on average are such poor investors that they actually underperform the very mutual funds they actually invest"

13:21 "The key to successful investing is to understand what Napoleon advised about military strategies: He said battles are never won on the field, they're won in the preparation stage"

15:26 "You have to just accept that markets are unpredictable and you must have discipline, you want to be a buyer when everyone is panic selling and you want to be a seller when everyone else is getting greedy. There is a simple although not easy way of doing that and it's called rebalancing your portfolio"

16:14 "What people don't understand is really how stocks are priced"

20:01 "People have this notion that if they can get in and out of certain asset classes or get in and out of certain markets, that's going to enhance their overall investment experience, but actually the opposite is true"

21:04 "The key is to understand how markets have changed over the last 70 years"

23:59 "It's not necessarily the mutual fund, it's the allocation and how you're actually positioning the overall accounts towards different areas of the markets"

24:55 "Here's the key: what investors need to focus on is not trying to choose a money manager or stock that they think will outperform…what you do want to focus on is putting your money in the asset classes that you believe are appropriate for you to hold"

28:43 "Investing is really simple; you need to have a well-thought-out plan to make sure you don't take more risk than you have the ability, willingness and need to take"

35:25 "When you have a fund that's outside of a retirement account and the manager is buying and selling, that's causing short-term gains which are the most expensive of gains. Now all of sudden you're paying more in taxes"

How the Financial Planning Landscape Made Way for Pure Financial Advisors - 5 Feb 27, 2016

Original publish date February 27, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed. In episode 5 of YMYW, Joe and Big Al discuss the financial planning landscape and why they chose to start Pure Financial. Big Al breaks down a few of the presidential candidates' tax plans. Plus, why women are better savers and investors than men.

00:00 - Intro

02:23 "Everyone needs a financial plan. Everyone absolutely needs a financial strategy to make sure they know what they need to be doing"

04:33 "We don't sell any products, there are no commissions generated to our firm"

08:17 "Our firm thinks it [the fiduciary rule] is a phenomenal thing, because we act as a fiduciary 100% of the time"

12:22 "We want to protect you against unscrupulous sales practices and things like that because we know the industry; we're in the business and we see the good, bad, ugly all day every day"

13:50 "In the tax realm, there are a lot of strategies he [Obama] wants to get rid of…right now I think it's important to realize what some of those strategies are so if they do apply to you, that you make sure you take advantage of them while they're still here"

14:28 "You can still do Roth IRA contributions for 2015 all the way up until April 15th of this year (2016)"

22:03 "Ted Cruz wants to do a flat tax; he wants to do a 10% flat tax across the board…who is that going to impact? It's going to impact the lower and middle class, while the wealthy will end up with a lot more money in their pockets"

27:10 "When you are married to a spouse who is making a lot of income, your self-employment income is pretty highly taxed, because you're already in the highest bracket and you've got self-employment tax to boot"

31:24 "Vanguard shows that women are the ones signing up for 401(k) plans and saving a larger piece of their salaries compared with their male counterparts"

Are You Doing Social Security in Retirement All Wrong? - 4 Feb 20, 2016

Original publish date February 20, 2016 (hour 2). Note that content may be outdated as rules and regulations have changed. In episode 4 of YMYW: are you doing your retirement all wrong?

Joe and Al discuss recent Social Security changes and which claiming strategies you shouldn't miss out on if you qualify (restricted application and file & suspend). Find out how you can make more informed decisions when incorporating Social Security into your overall financial strategies. The two finish off the hour explaining why working even one extra year can have a huge impact on your retirement.

1:59 "Money will have to last retirees a lot longer, so that's longevity risk"

7:29 "More older adults are retiring with outstanding debt"

11:32 "If you're 62 and older before the end of last year, you could still file a restricted application... Also, you have another deadline: April 30th: file for your benefits and then suspend them; these are the two things that are changing"

12:49 "The spousal benefit is half of the spouse's benefit"

16:43 "No Social Security benefits are taxable in California—zero"

17:34 "Congress just got rid of a few Social Security claiming strategies this year, so the new rules make it more important than ever to make informed decisions when incorporating Social Security into your overall financial strategies"

18:44"Those final few years that you actually work make a big, big difference in the success or failure of retirement."

23:40 "A lot of you, when you really sit down and look at your situation, it's a little bit tighter than you might want it to be"

34:55 "There's a lot of new things with the new tax bill that can benefit you from a permanent basis"

The Most Significant Financial Strategies to Implement Now - 3 Feb 20, 2016

Original publish date February 20, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed. In episode 3 of YMYW, Joe tells us about the most significant financial strategies to start implementing now; Surprising things the government wants to tax you on; and the return of "Tax Chat" as Big Al shares a couple of tax tips.

02:40 "You can't control the stock markets, you can't control interest rates, you can't control the price of oil..."

06:00 "You want to make sure you have enough capital in your overall portfolio to maintain that [retirement] lifestyle"

10:25 "We've been doing this radio show for over 10 years, we teach a lot of retirement courses at local universities and community colleges. If you go to our website we have a learning center with over 200 videos. What we try to do is make sure we empower people"

15:39 "Educate yourself to understand how much risk you're taking in the portfolio"

17:10 "Taxes are something that you actually do have some control over, as long as you know how to manipulate and utilize the tax code to your advantage"

31:29 "A lot of you are in the sandwich generation, and what the sandwich generation means is that you have elderly parents that you are caring for and then you still might have kids on the payroll, so money is going every which way except your retirement"

31:50 "One of the biggest financial risks to retirement is your own grown children"

How Negative Interest Rates and the President's Budget Proposal Impact You - 2 Feb 14, 2016

Original publish date February 14, 2016 (hour 2). Joe and Big Al discuss negative interest rates and how they could affect you. Plus, the President released this year's budget proposal! Big Al and Joe break it down and explain what the changes could mean for you and your beneficiaries.

4:24 "If you work an extra two years, it means that's two years less that you're taking from your portfolio and that's two years more that you're deferring your overall Social Security benefits"

10:22 "There are significant changes going on with Social Security; we are doing a webinar [on February 23rd, 2016] if you'd like to sit in the comfort of your own home and listen for an hour"

11:43 "For a long time economists believed that nominal interest rates or the amount of money received for depositing money was theoretically bound to zero"

12:05 "Lately, however, central banks from Europe to Japan have implemented a negative interest rate policy in order to stimulate economic growth"

19:18 "Here's what they're trying to eliminate: the backdoor Roth IRA, the stretch IRA, and step-up in cost basis at death"

19:55 "Here's how it [step-up in cost basis] works: when you pass away, your assets get stepped up to whatever they're worth at the date of death. Let's just say you bought a home for $100,000 and now it's worth $1 million and you pass away--you didn't sell it. When your kids get it and if they sell it for $1 million, do they have to pay gains on the $900,000 gain? The answer is no - it's a step-up in basis so it's as if your children bought that asset for $1 million. It works with stocks, real estate and anything outside of your retirement account, it gets that step-up in basis"

22:02 "Here's another change: adding RMDs at age 70 1/2 for Roth accounts"

24:08 "If it's a large account, your non-spouse beneficiaries are going to pay a ton of tax in those accounts if you have a large balance in those accounts"

26:47 "You want to convert while assets are down because if you convert now, the recovery with the future growth in the IRA is all tax-free"

28:22 "What you need to do right now is have a forward-looking tax strategy created so you can figure out what steps you need to do this year, next year and the future so you can stay out of higher tax brackets coming"

30:02 "If you have more than $3.4 million in a retirement account, you will no longer be able to contribute to retirement accounts. You can still save money but it won't be sheltered from tax"

31:25 "Capital gains is a lot lower rate than ordinary income rate, in fact capital gains for most people is 15%, but ordinary income tax rates go as high as 39.6% so it can be a huge tax savings"

80% of Participants Failed This Financial Literacy Test - 1 Feb 14, 2016

Original publish date February 14, 2016 (hour 1). Welcome to the Your Money, Your Wealth® podcast: retirement planning, investing, and tax reduction made fun. Hosts Joe Anderson, CFP®, and Alan "Big Al" Clopine, CPA of Pure Financial Advisors have been providing financial education on the Your Money, Your Wealth® radio show in Southern California since 2008, and on the Your Money, Your Wealth® television show in San Diego since 2014! In this, the first episode of the YMYW podcast, Big Al tries to stump Joe with the financial literacy test that Forbes says 80% of participants failed.

3:08 "Just because the balance of your overall portfolio goes down, that doesn't necessarily mean you lost money – that's volatility; that is normal in any type of market cycle"

7:03 "Another thing you should be doing is tax loss harvesting, so you want to harvest some of the losses if you have down positions. Sell those and buy something similar to take those losses on your tax return"

8:05 "An article out of Forbes Magazine reveals that 81% of Americans failed a basic financial literacy test"

8:44 "Planning for your retirement can be scary, but when you think you know what you're doing and you really don't, the final outcome could be really scary"

12:22 "What's interesting about this is a lot of folks who took the test were very confident in their abilities to retire successfully (yet 80% failed the test)"

20:59 "Which of the following types of long-term bonds typically have the highest yield? Triple A-rate corporate bonds, B-rated corporate bonds or treasury bonds?"

24:56 "Anything that comes out of a retirement account that you took a deduction for is going to be paid full ordinary income tax and the state of California tax"

26:11 "As a CPA I would honestly say, it's been 30 years+ in the business and it does amaze me how many people fail to get the message about tax planning until they make a mistake that costs them thousands of dollars"

32:10 "There is an age limitation on IRAs, so after 70 ½ you can no longer contribute to an IRA, however if you're over 70 ½ you can still contribute to your employer-sponsored plan"

34:06 "When do you want to do your Roth conversions? When the market is down!"

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