Your Money, Your Wealth

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

Show notes

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)

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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

Show notes

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

REQUEST your Retirement Spitball Analysis

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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

Show notes

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)

REQUEST your Retirement Spitball Analysis

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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

Show notes

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)

REQUEST your Retirement Spitball Analysis

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READ financial blogs

WATCH educational videos

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Connect With Us:

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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

Show notes

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

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

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

Show notes

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)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

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SUBSCRIBE to the YMYW Newsletter

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 - 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

Show notes

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)

REQUEST your Retirement Spitball Analysis

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READ financial blogs

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Connect With Us:

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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

Show notes

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)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

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Connect With Us:

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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

Show notes

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

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 - 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

Show notes

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

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Connect With Us: