The Stacking Benjamins Show

Latest Episodes:

Should You Look at "Risk" Differently? (with Len Penzo) SB1591 Oct 23, 2024

Show notes

Today we share a fresh perspective on personal and financial risk, featuring the always insightful Len Penzo (LenPenzo.com). Joe, OG and Len will dive into the complexities of managing your 401k and understanding the risk tolerance required to meet your goals. We'll share pivotal strategies for effective retirement planning and hopefully help you grasp why taking enough risk is crucial, especially for younger investors who have time to recover from potential losses. Listen in as we explore investment behaviors versus portfolio performance and how emotional decisions during market fluctuations can impact your financial journey.

We don’t just tackle numbers here. We'll also examine whether widening your approach to include career risks and the often-overlooked social risks that can open doors to new opportunities is a good strategy. We'll talk about on growing your employment opportunities, ensuring long-term wealth, and balancing financial and emotional satisfaction. Plus, there just may be a slight amount of banter about Halloween treats, the joys of IRS conundrums, and the misconceptions of viral TikTok financial advice.

To top it all off, we may or may not share stories about Joe’s adventures learning craps in Las Vegas, revealing the thrills and lessons of gambling. If you're searching for lessons, it may include the importance of knowing when to walk away, and the camaraderie forged at the casino tables. Whether you’re tuning in for practical financial strategies or just to enjoy some relatable stories and laughs, this episode is packed with takeaways on looking at risk differently in every facet of your life.

Introduction to Debt Management
Welcome to the Stacking Benjamin Show
Discussing Risk with Len Penzo
The Fortune Cookie Incident
Understanding Risk Tolerance
Career and Social Risks
Halloween Treats and Risks
Stocking Up for Halloween
Diving into Risk Management
TikTok Minute: Career Success
Doug's Trivia: Understanding 1031 Exchange
Listener Question: Employer-Sponsored IRA Plans
Vegas Stories and Gambling Tips

FULL SHOW NOTES: https://stackingbenjamins.com/len-penzo-halloween-1591

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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Seth Godin's Blueprint for Financial and Life Strategy (SB1590) Oct 21, 2024

Show notes

Grab your coffee mug and join us for a journey full of strategic insights and valuable life lessons. Business legend Seth Godin joins us to share his wisdom on financial strategy and personal success. From college applications to wedding planning, Seth's advice on using a strategic compass over an outdated map will help you navigate big decisions and avoid wasting time and potential. Plus, we explore the balance between effortless yet intricate service and strategic pricing, advocating for value over cutting costs like Walmart because, sometimes, the tension in the experience is what makes it memorable and rewarding. There are plenty more actionable takeaways in our discussion with one of the most prominent gurus in marketing. Mainly, we delve into why having a well-thought-out strategy for life and personal finance can make all the difference. Learn from Seth's rich experience—from guiding startups to success to creating impactful strategies.

We also explore the historical strategies that have shaped businesses like Yahoo and Google. Seth emphasizes the importance of vocalizing strategies, balancing personal agency with systemic constraints, and the essential threads of strategy: time, empathy, games, and systems. Using personal finance as a lens, Seth helps you understand complex concepts in a relatable way, underscoring how strategic thinking can transform everything from wedding expenses to retirement planning.

Of course, that's not all. In our headline segment, we share the results of a recent study by Harvard, Vanguard, and others on 401k plan "leakage." New rules allow people to take annual withdrawals from their retirement plans. Will people abuse this new rule? The results of this study are surprising, to say the least. We discuss how to use 401k loans, why we don't favor them, and strategies to plug leaks so that your financial boat doesn't sink.

On top of that, we also share trivia from Doug and much, much more! This may be your favorite Monday on Stacking Benjamins!

Run of Show

Morning Optimism and Weekend Plans

Saluting Our Troops

Special Guest: Seth Godin on Strategy

The Importance of Strategy in Personal Finance

College Applications and Life Strategies

Seth Godin's Background and Achievements

Understanding Strategy: Time, Empathy, Games, and Systems

Walmart's Competitive Edge

Freelancing on Upwork: A Race to the Bottom

Justifying Higher Prices

The Power of Peer Groups

Mentorship vs. Peer Groups

Personal Experiences with Peer Groups

Trivia Time with Doug

401k Loans and Retirement Plan Leakage

The Importance of Cash Reserves

Upcoming Events and Meetups

Consulting Firm Anecdote

FULL SHOW NOTES: https://stackingbenjamins.com/create-you-life-strategy-with-seth-godin-1590

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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Has Anyone Ever Gone Broke From Bad Tax Planning? (SB1589) Oct 18, 2024

Show notes

Have you ever met someone whose retirement was wrecked by poor tax planning? While tax planning is essential, one big-named figure in the financial community who's a tax expert says that tax planning may be over-emphasized. But is it? Today, we're joined by experts Deb Meyer (Beyond Budgets podcast), Sean Mullaney (FI Tax Guy YouTube Channel), and the guy behind the Earn & Invest podcast, Doc G. Our financial experts will debunk common tax myths and provide actionable insights for a secure financial future. They'll explore the essential differences between marginal and effective tax rates, and you'll learn how effective tax planning can positively impact your retirement. Discover how to leverage tax calculators to avoid dreaded tax surprises and understand the nuances between Roth and traditional retirement accounts. Our enthusiastic experts bring humor and real-life examples into the mix, making complex tax strategies accessible to everyone, whether you're an entrepreneur or planning for retirement. In the second half of our discussion, we shift focus to practical financial advice. Discussions revolve around the temptation to overly optimize tax shelters and the importance of balancing tax efficiency and accessible funds. We cover concerns about the 'tax torpedo' affecting Social Security taxes and highlight the nuanced approaches required for better tax planning in an investor's journey. The insights shared aim to demystify tax planning for listeners, helping them shape sound financial strategies tailored to their personal circumstances.

At the midway point, we'll pause for Doug's trivia question, today focused on a BIG tax case: Al Capone's run-in with the IRS. We'll share stories about his untaxed empire and discuss Walt Disney's clever tax maneuvers. We think you'll laugh through valuable tips on diversifying tax statuses and recovering tax bases. Hopefully, you'll leave with a better grasp of maximizing your tax efficiency and preparing for a financially stable future.

Ignition Sequence and Lift-Off
Introduction to the Stacking Benjamin Show
Meet the Hosts and Guests
Tax Talk and Trivia Teasers
Welcoming the Financial Experts
Diving into Tax Planning
Effective vs Marginal Tax Rates
Tax Planning for Entrepreneurs
The Importance of Tax Diversification
Trivia Challenge Begins
Al Capone's 1931 Income Mystery
Guessing Al Capone's Untaxed Income
Revealing the Real Answer
Financial Nerds and Tax Concerns
The HSA Debate
Annuities and Tax Gotchas
Cash Value Life Insurance
Podcast Highlights and Farewells
S-Corp vs Sole Proprietor

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Score Big with Creative Income Strategies (SB1588) Oct 16, 2024

Show notes

Explore how to score big with creative income strategies with us! Today, we'll dive into an in-depth case study on private equity in professional sports teams and discover how to use similar strategies to increase your wealth growth. You'll learn actionable advice on maximizing revenue sources, including tactics like Roth IRA conversions, covered calls, and creative investments like drop shipping during retirement and car rentals. We'll share a host of diversified financial insights that can help optimize your assets...all while having a bit of fun along the way.

Later, catch our hilarious TikTok minute where we highlight a woman's misguided attempt to buy quarters on Amazon. In the 'Better Call Saul' segment, we tackle a listener’s question about retirement planning, providing practical tips that can be applied to everyday life.

Of course, you don't want to miss Doug's trivia segment, where you’ll gain intriguing knowledge, like the anniversary of Marie Antoinette's last day and the history of Cutco knives. Hopefully you'll walk away with both valuable takeaways and a smile.

Run of Show:

Unexpected Shopping Spree
Welcome to the Stacking Benjamin Show
Money Urologists and Case Analysis
The Value of Cash Payments
Inflation and Economic Insights
Private Equity in Professional Sports
Leveraging Personal Finances
Creative Income Streams
Maximizing Investment Returns
Flexibility in Financial Planning
Mark Cuban's Business Insights
Real Estate Ventures and Lessons
The TikTok Minute: Math Mishap
Trivia Time with Doug
Roth Conversion Strategies
Show Wrap-Up and Listener Review

FULL SHOW NOTES: https://stackingbenjamins.com/big-money-in-sports-1588

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ben Orlin Reveals the Fun Side of Math! (SB1587) Oct 14, 2024

Show notes

Do you think you're bad at math? Who doesn't! Whether you're an algebra whiz or struggle with subtraction, today's episode is for you. Join us as we dive into the exciting intersection of math and finance with Ben Orlin, author of 'Math with Bad Drawings.' We'll uncover the unexpected fun in mathematics and learn how understanding concepts like statistics and standard deviation can reveal the hidden stories within numbers. Ben's perspectives on embracing mistakes and the intrinsic link between math and finance offer a fresh look at these often daunting subjects.

In our headline segment, discover the top strategy for achieving millionaire status through consistent investment in--believe it or not--nothing fancy! Danny Noonan shares the results of Fidelity insights into the lives of '401k millionaires,' spotlighting the power of patience and discipline over high-risk opportunities, underscoring sustainable financial growth.

Finally, Doug enlivens the discussion with intriguing trivia on the differences between mean and median averages. Doesn't that sound hilarious?

Of course, there's much more, so join us as we weave together actionable financial advice with engaging stories, making complex concepts like math and finance accessible and relatable for everyone.

RUN OF SHOW

Monday Morning Vibes
Financial Wisdom with a Twist
Introducing Today's Mentor: Ben Orlin
Math and Bad Drawings
The Beauty of Mathematics
Breaking the Economy with Dice
Statistics: Lies, Damn Lies, and More
Tweaking the Guinea Pig Bed
Embracing Mistakes in Learning
The Power of Walking Away
Unexpected Solutions in Math
Good vs. Great Mathematicians
Math and Mentorship
The Collaborative Nature of Math
Understanding Averages
The Storytelling Power of Math
The Importance of Consistent Investing
Wrapping Up and Final Thoughts

FULL SHOW NOTES: https://www.stackingbenjamins.com/ben-orlin-sb1587/

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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Stacking Health or Wealth? Your Retirement Dilemma (SB1586) Oct 11, 2024

Show notes

Today's show tackles the age-old dilemma: is it better to have good health or more money during your retirement years? Join our lively roundtable as we discuss balancing financial planning with health priorities, featuring insights from Jesse Cramer of 'The Best Interest Podcast', Paula Pant from 'Afford Anything', and OG. Learn how different retirement stages can affect your spending habits, and explore creative ways to integrate health expenses into your financial plan. Plus, discover actionable tips on motivating yourself to stick to a healthy lifestyle and whether to invest in gym memberships or home equipment. Don't miss our contributors' take on the potential misuse of Health Savings Accounts (HSA) and their hilarious anecdotes about life and fitness.

Run of Show:

Introduction and Show Opening
Panel Introduction and Health vs. Wealth Debate
Segway and Scooter Anecdotes
State Farm Advertisement and Personal Stories
Health and Retirement Planning
Trivia Question and SNL Discussion
Comedian Salaries Revealed
SNL Cast Member Earnings
HSA: The Health Savings Account Debate
Navigating Healthcare Plans
Choosing the Right Workout Routine
Podcast Highlights and Upcoming Guests
Final Takeaways and Closing Remarks

FULL SHOW NOTES: https://www.stackingbenjamins.com/good-health-vs-more-money-retirement

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What Ugliness Is Hiding In Your Investment Portfolio? (SB1585) Oct 09, 2024

Show notes

A recent Investment News piece shines a light on investment advisors (in this case we think that should read "investment salespeople") are recommending some truly ugly investments to investors. We'll dive into how the work, so hopefully you'll discover why certain alternate investments might send alarming signals for your portfolio. We go back in history to share hints at market risks that often go unnoticed until it's too late. We'll talk about the dangers of illiquidity, high fees, and obscure ways of measuring returns. You'll come away learning some shocking truths about leveraged investments and alternative products that make you question their place in any strategy.

In our TikTok Minute, we'll share which bank one comedian calls the perfect partner for your needs. Is he right? Plus, later we'll help a listener who thought he'd Better Call Saul...Sehy and OG. Maybe OG needs to re-velvet his hammer on this one, and he manages to go into a diatribe that you shouldn't miss. We'll talk about career decisions, having more money than "Coast FI," and more on today's episode.

Rounding out the episode, Doug shares his amazing trivia question, including YouTube's billion-dollar origins AND a ton of other events that happened on today's date in history.

RUN OF SHOW:

Countdown to Live Show
Introduction and Show Overview
Investment Warning: Be Cautious
Investment Strategies and Mistakes
Alternative Investments: Risks and Rewards
Understanding Business Development Companies
The Reality of Non-Traded REITs
Final Thoughts on Liquid Investments
Interval Funds
Doug's Trivia Question
The TikTok Minute
Better Call Saul: Career Advice for Michael
Conclusion and Listener Reviews

FULL SHOW NOTES: https://www.stackingbenjamins.com/beware-investments-navigate-investing-waters

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The Robots Are Coming For Our Jobs (with Josh Brown) SB1584 Oct 07, 2024

Show notes

Josh Brown joins us on today's episode for a thoughtful investment discussion in Mom's basement. Discover why "buying the robots" is a must, why everyone having money is a big fat negative for the economy and more. It's a wide-ranging conversation with one of the top advisors in the USA, and we're excited about all that Josh will share with our Stacker audience.

In our headline segment, we'll discuss the importance of understanding insurance, especially in light of Hurricane Helene. Learn how to make your donations count and why revisiting your financial plan is essential for future confidence.

Later, we'll shift gears to Hollywood, where aging protagonists are thrown back into action. Jeff Bridges reunites with his past in a gripping FX series, while Gary Oldman’s stellar performance in Apple TV's 'Slow Horses' takes the spotlight, though its pace might test your patience. Don't miss the brief nods to John Lithgow and Stanley Tucci and a fleeting mention of Mel Gibson, rounding out an episode rich in actionable insights and entertainment industry intrigue.

Introduction and Apple Music Dilemma
Apple Maps and Pretzel Problems
Saluting the Troops and Show Introduction
Robots and Automation Discussion
Hurricane Helene and Financial Lessons
Retirement Planning Insights
Nvidia and Technology Takeover
Pandemic's Impact on Inflation
Media's Role in Financial Information
Hollywood vs. Reality: The Truth About Wall Street
The Wolf of Wall Street's Influence on Modern Traders
Josh Brown's Perspective on Market Culture
The Importance of Financial Designations
Hurricane Helene: Impact and Relief Efforts
The Real Cost of Insurance and Rebuilding
Charitable Giving: Time, Expertise, and Goods
Upcoming Events and Meetups
Final Thoughts and Takeaways

FULL SHOW NOTES: https://www.stackingbenjamins.com/josh-brown

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What Hidden Fees and Costs are Sneaking Money From Your Wallet? (SB1583) Oct 04, 2024

Show notes

Here's a shock: our least favorite brokerage company is in the news again with some monster hidden fees. Robinhood is accused of charging customers a huge "spread" between the amount option buyers pay and the amount sellers receive. While this isn't a charge on the statement, it's a lot of money (nearly double) that other companies charge.

This topic got us thinking: what hidden charges, expenses, and costs exist in our life that we overlook or choose to ignore? How much are all of THESE costs adding up? We have the perfect triumvirate for this discussion. Jen Smith, one half of the Frugal Friends duo joins us (they talk consumption non-stop on their podcast). Roger Whitney chimes in (his Retirement Answer Man helps people control excess costs in retirement or when prepping). OG also joins in, with all of his experience helping clients reach their goals. It's a wide ranging, fun discussion, from the cost of pollution to hidden Doordash costs we didn't know about!

Of course, halfway through this episode, we take a break to challenge these contributors to a round of Doug's epic trivia.

FULL SHOW NOTES: https://www.stackingbenjamins.com/hidden-fees-and-costs

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!

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Quit Saving Sooner, Live Freer (SB1582) Oct 02, 2024

Show notes

Learn the secrets behind never worrying about saving money again! We share the story of an individual who invested early and effectively, reaching financial security by 25, and how YOU can apply these principles regardless of age. Our main discussion highlights how to achieve financial freedom and the importance of staying disciplined with your savings over time, offering valuable insights into the pitfalls and opportunities of early investing and the flexibility it can bring to your lifestyle choices later on. Plus, we explore the balance between traditional investments and investing in personal growth opportunities for a brighter financial future.

In our TikTok minute, comedian Greg Warren addresses compounding interest and how the accumulative consequences of poor decisions can pile up in life. This sets the stage for our Better Call Saul...Sehy and OG segment, where we tackle a listener's question about disability insurance, offering practical advice for securing comprehensive coverage and understanding the importance of one's own occupation policies. We provide actionable tips and clear explanations to help anyone navigate the often confusing insurance world.

Doug's trivia this episode revolves around the band Oasis and the quirky history of Ticketmaster fees, providing a nostalgic trip down memory lane for music fans. We wrap up with listener feedback, upcoming event announcements, and highlights like Joe's adventurous dining experiences in Peru (including some surprising menu items!). Tune in for a packed episode filled with financial wisdom, humor, and a dash of Doug's signature fun facts.

Show Rundown