The Stacking Benjamins Show

• What Are YOU Worried About Financially? (LIVE From FinCon 2025) SB1737

  What happens when you throw a bunch of money nerds into one room, add microphones, and sprinkle in a little economic chaos? You get this live recording from FinCon in Portland, where Joe Saul-Sehy, Paula Pant, Jesse Cramer, and Matthew Tarr tackle today’s most pressing financial questions head-on—with plenty of laughs along the way. From housing headaches to healthcare hurdles, nothing is off the table as the crew breaks down the issues shaping your money right now. Housing prices got you wondering if you should rent, buy, or just live in your car with an Amazon Prime subscription? We dig into the real trade-offs in today’s market. Worried about a looming recession or high-interest rates eating away at your financial confidence? You’ll walk away with strategies that keep you focused and resilient when headlines try to spook you. And for those plotting an early retirement, the group pulls apart the rising cost of healthcare and why conservative investment strategies may be your best friend. At its core, this episode is about tuning out the noise and zeroing in on what matters: a solid plan, smart decisions, and a community of people who know that money is just the tool—not the destination. Whether you’re trying to hit FI, weather market storms, or simply avoid panic-selling your investments, this conversation from the heart of FinCon will leave you with perspective, strategy, and maybe even a grin. Why renting vs. buying isn’t a one-size-fits-all answer (and what today’s market means for you) How to prepare for recession chatter without losing sleep The ripple effect of high-interest rates on your wallet and investments Smart approaches to healthcare planning in early retirement Practical strategies for building a strong investment plan that outlasts market swings Reflections on community, optimism, and financial resilience from the FinCon floor Points to Chew On: Would you rather own a house in this market—or rent and keep flexibility? How do you personally prepare for recession fears without derailing your long-term plan? If healthcare costs keep climbing, how will that affect your retirement timing or strategy? FULL SHOW NOTES: https://stackingbenjamins.com/live-from-fincon-2025-173 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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• David Gardner on Breaking the Rules of Investing (SB1736)

  What happens when you stop playing it safe and start playing it smart? In this episode, Joe Saul-Sehy, OG, and Neighbor Doug sit down with David Gardner, co-founder of The Motley Fool, to explore how breaking traditional investing “rules” can sometimes lead to the biggest wins. From his early career to building a community of investors who think differently, David shares the lessons that shaped his approach and why focusing on long-term investing (with a dash of joy) is the key to building wealth. This isn’t just theory—David opens up about the real-world evolution of financial advice, the importance of conscious capitalism, and why advisors need to shift from just picking stocks to becoming true guides in an era where investment products are commodities. Along the way, the basement crew mixes in a few unexpected detours (yes, including some movie talk), reminding us that money doesn’t have to be boring to be meaningful. If you’ve ever felt like the “safe” path with your money was leading you in circles, this episode offers a fresh perspective from one of the most influential voices in modern investing. Get ready to rethink the rules, laugh along the way, and come away with strategies to make your portfolio—and your life—more rewarding. Why breaking conventional investing “rules” can sometimes be your best move The evolution of The Motley Fool and its impact on everyday investors How long-term thinking beats short-term noise in building wealth The role of conscious capitalism and why businesses matter beyond profits Why financial advisors need to pivot their focus to guidance, not just products How criticism shaped David Gardner’s career and what he learned from it Points to Ponder During the Episode When’s the last time you broke a “money rule,” and did it pay off—or backfire? Do you believe financial advisors should focus more on guidance than investment selection? What’s one company or stock you’ve stuck with long-term—and why? Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• How to Sidestep the 4 Culprits Wrecking Middle Class Retirement (SB1735)

  What really derails retirement dreams? Spoiler alert: it’s not always the stock market or your 401(k). Sometimes it’s sneaky habits—like leaning too hard on your house as a retirement plan or ignoring how long you might actually live—that quietly gnaw away at your financial future. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug dig into the most common middle-class retirement killers and how you can sidestep them. But this isn’t your average checklist of “don’t do that.” The team dissects questionable advice floating around internet forums, debates stock splits and diversification, and even finds time to unravel why owning a cat might make you a magnet for gangster-level problems. Add in Doug’s trivia about a famous singer’s real name, and you’ve got an episode that’s equal parts practical and delightfully unpredictable. Whether you’re worried about stretching your retirement savings or just looking for sharper ways to think about financial advice, this episode offers both reassurance and reality checks. So grab your favorite mug (or maybe your cat), settle into your seat, and get ready to learn how to protect your retirement from the biggest threats—while laughing at the absurdity along the way. What You’ll Learn in This Episode: The habits that quietly sabotage retirement plans (and what to do instead) Why your house may not be the slam-dunk retirement strategy you think it is The risks of living longer than you expect—and how to plan for it How to sniff out sketchy financial “tips” before they lead you astray The surprising traps behind stock splits, diversification myths, and overconfidence Why even well-meaning advice can backfire if you don’t look at the big picture Questions to Ponder (or Debate in the Basement Facebook Group): Which retirement habit do you think trips people up the most—and why? If you had to choose, would you rather rely on your house equity or a diversified portfolio to fund retirement? What’s the worst financial “tip” you’ve ever heard online (or maybe even followed)? FULL SHOW NOTES: https://stackingbenjamins.com/habits-that-destroy-middle-class-retirement-dreams-1736 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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• How Are You Creating Your Happiest Life? (SB1734)

  If having more money guaranteed happiness, we’d all just set our financial targets, cash the checks, and live joyfully ever after. But as Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Joel Larsgaard (How to Money) unpack in this lively roundtable, life’s richest rewards often have little to do with your net worth. They explore why some wealthy people still feel miserable, how Benjamin Franklin’s approach to living can still teach us a thing or two, and why optimism may be your secret investing edge. From the science that says peak life satisfaction might just happen around age 70, to the underrated role of good friends in a rich life (financially and emotionally), this episode blends timeless wisdom with modern money smarts. Whether you’re chasing financial independence, already there, or just trying to make sure your journey is as fulfilling as your destination, you’ll find ideas you can put into practice right now. And because this is the basement, expect the conversation to meander into relatable stories, some eyebrow-raising trivia, and a few debates on what balance really looks like when you factor in both spreadsheets and smiles. What You’ll Learn in This Episode: Why money alone won’t guarantee happiness (and what really does) How Benjamin Franklin’s life principles still apply in today’s financial world The connection between optimism and long-term investing success The surprising age when happiness may peak (and what to do before you get there) How to balance financial independence with enjoying the present Why strong social circles are a must-have part of your wealth plan Questions to Ponder (and maybe share your answers with the Basement Facebook Group!): Do you think your happiness will peak at a certain age—or is it more about circumstances? How do you balance saving for the future with enjoying your money today? What’s one small, intentional change you’ve made that had a big impact on your happiness? Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• How to Lead (and Evaluate Good Leadership) with David Gergen (SB1733)

  What can you learn about leadership from someone who’s served four U.S. Presidents, navigated some of the most intense moments in American politics, and still believes the future depends on building more leaders, not fewer? In this Greatest Hits Week replay, Joe Saul-Sehy, OG, and Neighbor Doug welcome David Gergen—former White House advisor, Harvard professor, and author—to the basement for a masterclass on leadership that applies as much to your career and investments as it does to running a country. Gergen pulls back the curtain on life inside the White House, from the early lessons he learned in the Navy to the behind-the-scenes moments that revealed the human side of Presidents. Along the way, he shares what separates great leaders from the rest, how to evaluate leadership in others (and yourself), and why service and responsibility are the cornerstones of lasting influence. Whether you’re leading a team at work, managing your family’s financial future, or just trying to be the kind of person others trust, you’ll find plenty here to sharpen your approach. And because no visit to the basement is complete without some SB-style surprises, you’ll also hear stories of presidential humor gone sideways, a White House prank or two, and reflections on how good leadership isn’t about perfection—it’s about purpose. Plus, the guys tackle a listener question on investing without specific goals, and Doug tests the panel’s trivia chops with a leadership twist. What You’ll Learn in This Episode: How David Gergen defines real leadership (and how it’s changed over time) The telltale signs you’re working with—or for—a great leader Lessons from the Navy, the West Wing, and history’s most memorable leaders Why building leaders is just as important as being one Practical ways to evaluate leadership in politics, business, and investing How a clear sense of service can make you a better investor and decision-maker Questions for you while you listen (share with our Facebook group!): Who’s the best leader you’ve ever worked for, and what made them stand out? How do you evaluate whether someone is worth following—whether in politics, business, or life? What’s one leadership skill you wish more people would develop? Learn more about your ad choices. Visit podcastchoices.com/adchoices

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