Episodes

  • Has Anyone Ever Gone Broke From Bad Tax Planning? (SB1589)

    Has Anyone Ever Gone Broke From Bad Tax Planning? (SB1589)
    Oct 18 2024
    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 Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 7 mins
  • Score Big with Creative Income Strategies (SB1588)

    Score Big with Creative Income Strategies (SB1588)
    Oct 16 2024
    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! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 4 mins
  • Ben Orlin Reveals the Fun Side of Math! (SB1587)

    Ben Orlin Reveals the Fun Side of Math! (SB1587)
    Oct 14 2024
    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 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 9 mins
  • Stacking Health or Wealth? Your Retirement Dilemma (SB1586)

    Stacking Health or Wealth? Your Retirement Dilemma (SB1586)
    Oct 11 2024
    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! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr
  • What Ugliness Is Hiding In Your Investment Portfolio? (SB1585)

    What Ugliness Is Hiding In Your Investment Portfolio? (SB1585)
    Oct 9 2024
    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! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    59 mins
  • The Robots Are Coming For Our Jobs (with Josh Brown) SB1584

    The Robots Are Coming For Our Jobs (with Josh Brown) SB1584
    Oct 7 2024
    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! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 19 mins
  • What Hidden Fees and Costs are Sneaking Money From Your Wallet? (SB1583)

    What Hidden Fees and Costs are Sneaking Money From Your Wallet? (SB1583)
    Oct 4 2024
    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! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 9 mins
  • Quit Saving Sooner, Live Freer (SB1582)

    Quit Saving Sooner, Live Freer (SB1582)
    Oct 2 2024
    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 Introduction and Setting the Stage Welcome to the Stacking Benjamin Show Today's Topic: Never Worry About Saving Money Again Headline: What If You Never Had to Think About Saving Money? The Power of Compounding and Investing Early Challenges and Pitfalls of Early Investing Flexibility and Lifestyle Changes Starting Late: It's Never Too Late to Begin Trivia Time with Doug Money and Reconciliation College Sales Experience TikTok Minute: Comedian Greg Warren Disability Insurance Dilemma Listener Feedback and Reviews Upcoming Events and Final Thoughts Joe's Peru Adventure FULL SHOW NOTES: https://www.stackingbenjamins.com/never-worry-about-saving-money Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 8 mins