Episodes

  • Tales of Financial Horror (and how we exorcised them) SB1755

    Tales of Financial Horror (and how we exorcised them) SB1755
    Oct 31 2025
    Pop quiz: What's scarier than a haunted house? Opening your credit card statement after a "just this once" shopping spree turned into a six-month spiral. Joe Saul-Sehy and Neighbor Doug gather 'round the basement campfire with Doc G (Jordan Grumet from Earn and Invest), Jesse Cramer (Personal Finance for Long Term Investors), and special guest Emily Egashira—AKA Your Friend Em from TikTok and Instagram fame—to share the financial horror stories that still wake them up at night. We're talking ghostly car-leasing nightmares, investment decisions that refuse to stay buried, and the kind of money mistakes that haunt you long after Halloween is over. But here's the thing about financial horror stories: they're only scary if you don't learn from them. Every tale in this episode comes with the lesson that could've prevented it—the red flag that got ignored, the advice that should've been followed, the moment when "this seems like a bad idea" got drowned out by "but everyone else is doing it." From impulse purchases that turned into long-term regrets to the financial advice that sounded great... until it didn't, this crew proves that the scariest monsters aren't in the movies. They're in our bank accounts, our retirement plans, and that subscription we forgot to cancel three years ago. Plus: Doug delivers Halloween trivia with a full-moon twist, because even financial terror deserves a side of fun. What You'll Walk Away With: • Real financial horror stories from people who lived to tell the tale (and learn from it) • The common thread in most money disasters—and how to spot it in your own life • Why car leases, "great investment opportunities," and "everyone's doing it" should always make you pause • How to turn your own financial frights into lessons instead of letting them haunt you forever • The confidence to say "no" when something feels off, even if you can't explain why This Episode Is For You If: • You've ever made a money decision you immediately regretted (welcome to the club) • You want to learn from other people's expensive mistakes instead of repeating them • You've got a financial skeleton in your closet and need to know you're not the only one • You appreciate brutal honesty wrapped in humor—because laughing at financial pain is cheaper than therapy • You're ready to face your money fears instead of hiding from them until tax season FULL SHOW NOTES: https://stackingbenjamins.com/money-nightmares-wallet-portfolio-credit-1755 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 1 min
  • Banishing Money Monsters: How to Talk Money With Anyone (Partners, Roommates, or Coworkers) SB1754

    Banishing Money Monsters: How to Talk Money With Anyone (Partners, Roommates, or Coworkers) SB1754
    Oct 29 2025
    You know what's truly terrifying? Realizing you and someone you share money decisions with have completely different ideas about finances—and you're both convinced you're right. Joe Saul-Sehy and OG welcome Doug and Heather Bonaparte, a CFP and business partner duo who've mastered the art of not killing each other over finances. And when you work together AND live together? Let's just say they've had plenty of practice navigating the financial frights that haunt any relationship where money's involved. Whether you're married, dating, splitting rent with a roommate, or partnering on a business venture, the same money monsters show up: the "fair split" debates, the family expectation zombies that won't stay dead, and those vampiric spending habits that drain shared accounts when you're not looking. Doug and Heather share what actually works—the timing tricks, the tone shifts, and the teamwork strategies that keep financial conversations from turning into horror shows, no matter who you're talking to. This isn't about becoming perfect financial partners overnight. It's about exorcising the money demons before they possess your most important relationships—romantic, professional, or otherwise. Plus: Joe and OG stir the cauldron with Halloween movie talk and trivia, because even the scariest conversations are better with a little basement humor. What You'll Walk Away With: How to start money conversations without summoning the spirits of past arguments (works for spouses, roommates, business partners, you name it) Doug and Heather's hard-won strategies for navigating disagreements when money and relationships overlap Why "financial transparency" isn't about policing every purchase—it's about understanding each other's money ghosts The three things any financial partnership needs to align on before the little stuff stops haunting you Permission to be messy while you figure this out (even CFPs have money fights) This Episode Is For You If: You share financial decisions with ANYONE—a partner, roommate, business associate, or family member Money conversations feel like walking through a haunted house blindfolded Someone else's financial habits make you want to scream louder than a horror movie victim You're tired of being cast as the villain every time you want to discuss shared expenses You need proof that even professionals who literally do this for a living still have to work at it FULL SHOW NOTES: https://stackingbenjamins.com/money-communication-horror-stories-1754 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 10 mins
  • Real Money Horror Stories (And How Not to Star in Your Own) SB1753

    Real Money Horror Stories (And How Not to Star in Your Own) SB1753
    Oct 27 2025
    What's scarier than a haunted house? Looking at your retirement account after ignoring it for five years. Joe Saul-Sehy, OG, and Doug welcome back Chuck Jaffe (Money Life with Chuck Jaffe) for his legendary annual Halloween visit—and this year, he's bringing two treats to the basement. First up: Chuck's Halloween Money Game for kids. Picture this: trick-or-treaters can take one piece of candy and walk away... or they can play a game where they might win more candy, actual money, or lose it all. It's economics wrapped in a Snickers bar. Chuck breaks down how each choice teaches kids (and parents) about risk, reward, delayed gratification, and why sometimes the safe bet is actually the smart bet. If you've got kids—or just want a genius way to gamify money lessons—you'll want to steal this. Then things get spooky. Real Stackers share their most bone-chilling financial horror stories: the credit union error that nearly cost someone their house, the coworker's "advice" that turned into a disaster, and the procrastination that haunted someone for years. These aren't fictional frights—they're real mistakes that real people are still recovering from. And every story comes with the lesson that could've prevented it. Plus: Doug's trivia takes a Halloween turn (naturally), and Joe and OG debate whether government incentives are more trick or treat. What You'll Walk Away With: Chuck Jaffe's brilliant Halloween Money Game—how to teach kids about risk, reward, and smart decisions using candy The economic principles hiding in every trick-or-treat choice (and how to explain them without killing the fun) Real Stacker horror stories: the financial mistakes that haunt people for years The red flags that could save you from starring in your own money nightmare Why the scariest financial advice often comes from people who mean well This Episode Is For You If: You want a creative way to teach kids about money that doesn't involve a boring lecture You've ever made a financial decision you wish you could take back You want to learn from other people's mistakes instead of making them all yourself You've got a money skeleton in your closet and want to know you're not the only one FULL SHOW NOTES: https://stackingbenjamins.com/frightening-halloween-stories-with-chuck-jaffe-1753 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
  • You've Got Enough Money to Quit. Should You? SB1752

    You've Got Enough Money to Quit. Should You? SB1752
    Oct 24 2025
    Here's a question nobody in the FIRE movement talks about: What if you reach financial independence... and don't want to quit? Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Doc G (Earn & Invest) tackle the idea of Reverse FIRE—people who've hit their number but choose to keep working anyway. And before you roll your eyes, hear them out. Because it turns out that having enough money doesn't automatically make you happy. And for a lot of people, walking away from work means walking away from purpose, identity, and the structure that kept them sane. The question isn't just "can I afford to retire?"—it's "what am I retiring to?" This conversation gets real about the hidden costs of quitting too soon, why some financially independent people feel guilty for wanting to work, and how to think about retirement not as a finish line but as a design problem. Whether you're sprinting toward early retirement or secretly wondering if you'd be bored out of your mind, this episode will make you rethink what freedom actually looks like. Plus: Doug's T-shirt trivia takes a weird turn (as always), and the crew proves that the best financial conversations happen when nobody's trying to sell you a course. What You'll Walk Away With: • Why "enough money" doesn't equal "enough purpose"—and what to do about it • How to think about work after financial independence (hint: it's not all or nothing) • The identity crisis nobody warns you about when you stop working—and how to avoid it • What financially independent people actually do with their time (spoiler: many keep earning) • Permission to want both: financial security and meaningful work Before You Hit Play, Think About This: If money wasn't an issue tomorrow, would you keep doing what you're doing? If the answer is "no"—why are you still doing it? And if the answer is "yes"—what does that tell you about retirement? Drop your take in the comments. The basement wants to know: Are you racing toward FIRE, or are you building something you never want to leave? 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 6 mins
  • Your Money Problems Aren't Math Problems (They're People Problems) SB1751

    Your Money Problems Aren't Math Problems (They're People Problems) SB1751
    Oct 22 2025
    Here's the secret nobody tells you: your money problems probably aren't math problems. Joe Saul-Sehy and OG sit down with Carl Richards—financial planner, New York Times columnist, and the guy behind those brilliant "Sketch Guy" drawings that make money actually make sense. Carl's spent his career helping people untangle their relationship with money, and his big insight? Most of us are overthinking it. Your financial plan shouldn't feel like a calculus final. It should feel like a map you can actually follow. Carl breaks down why emotions (not spreadsheets) drive most money mistakes, how to cut through the noise that keeps you paralyzed, and why the simplest plan is usually the one you'll actually stick to. If you've ever felt like you're "doing it wrong" because your strategy doesn't involve leveraged ETFs or cryptocurrency mining, this conversation will be a relief. Then Joe and OG dive into the options trading debate. Is it a legitimate tool for managing concentrated stock risk, or just financial cosplay for people who watch too much CNBC? They break down when options might make sense, when they're just expensive complexity, and how everyday investors should think about them (if at all). Plus: travel stories, Neighbor Doug's trivia (where he definitely brags about something), and proof that you can get smarter about money without wanting to take a nap. What You'll Walk Away With: Carl Richards' framework for simplifying your financial life—and why "The Behavior Gap" matters more than your rate of return Why the emotions behind your money decisions matter more than the math (and how to work with them, not against them) How to filter out financial noise and focus on the handful of things that actually move the needle The truth about options trading: when it's a smart risk management tool and when it's just expensive gambling Permission to keep your plan simple—even if it feels like everyone else is doing something fancier This Episode Is For You If: You feel like everyone else has figured out money except you Financial jargon makes you want to hide under a blanket You've got a solid income but still feel anxious about your money decisions You'd rather learn through real stories than get lectured by a guy in a suit You want to finally understand why you make the money choices you do (good and bad) FULL SHOW NOTES: https://stackingbenjamins.com/how-to-manage-your-money-goals-and-life-with-carl-richards-1751 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 14 mins
  • Should You Drain Your Emergency Fund? (And 4 Other Money Questions Keeping You Up) SB1750

    Should You Drain Your Emergency Fund? (And 4 Other Money Questions Keeping You Up) SB1750
    Oct 20 2025
    You've got questions. We've got two CFPs and a former planner ready to hash it out. Joe Saul-Sehy, OG, Doug, and CFP Anna Allem tackle the money decisions you're actually losing sleep over—and here's the thing: they don't always agree on the answer. That's the point. Should you drain your emergency fund to pay off debt? Is whole life insurance for your kids a smart move or an expensive mistake? How much life insurance do you actually need (not what some calculator tells you)? And when life throws you a curveball—layoff, surprise expense, major purchase—what's the move? With Joe Saul-Sehy's 16 years in financial planning, OG's CFP perspective, and Anna's insights, you'll hear how experienced voices think through these decisions differently—and why your answer might be different than all of theirs. Because the real skill isn't finding THE right answer; it's learning how to make YOUR right call. This episode is for anyone who's ever stared at their bank account thinking, "I know I should do something... but what?" Plus: Doug delivers trivia about the first auto insurance policy (because of course), the gang weighs in on athlete endorsements and reverse mortgages, and there's a TikTok money tip that sparks some debate. What You'll Walk Away With: • How experienced financial minds approach the emergency fund dilemma differently—and what that means for your situation • The whole life insurance debate: when it makes sense for kids and when you're better off elsewhere • A framework for figuring out how much life insurance you actually need—and why the "rules of thumb" don't always work • What to do when your financial plan meets real life (layoffs, surprise bills, major purchases) • The confidence to make a decision even when experts would handle it differently Before You Hit Play, Ask Yourself: What's the one money question you keep Googling but still don't feel confident about? If you're second-guessing your emergency fund, your insurance, or a big financial move, this episode is your permission to stop spinning and start deciding. Got a question we didn't cover? Call in to the show! StackingBenjamins.com/Voicemail FULL SHOW NOTES: https://stackingbenjamins.com/answering-your-burning-financial-questions-1750 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 11 mins
  • What Lucky People Do Differently With Money (SB1749)

    What Lucky People Do Differently With Money (SB1749)
    Oct 17 2025
    Think some people just have all the luck? Think again. Joe, OG, Paula Pant (Afford Anything), and Chris Luger (Heavy Metal Money) break down what separates people who catch breaks from those who don't...and spoiler alert: it's not about being in the right place at the right time. It's about what you DO when opportunity shows up. And before that: how you create the conditions for opportunity to find you in the first place. This episode digs into three moves that make luck happen: staying curious (even when you think you know the answer), being generous (yes, it pays off financially), and staying flexible when life throws you a curveball. Whether you're stuck on a money decision, feel like you're missing opportunities, or just want to stop watching other people win, this conversation will shift how you see "luck." Plus: Doug's trivia gets weird (what even IS a buttload?), the gang debates pumpkin spice season, and you'll hear stories that prove the best financial wins rarely go according to plan. What You'll Walk Away With: The one thing "lucky" people do that creates more opportunities—and how to start doing it today Why helping others might be your best financial strategy (and the science behind it) How to spot opportunities you're currently walking past What to do when your financial plan falls apart (hint: the flexible win) Permission to try something new, even if you're not sure it'll work Before You Hit Play, Think About This: What's one time something good happened to you? ...not because of random chance, but because you were curious, helped someone, or said yes to something outside your comfort zone? That's the kind of "luck" we're talking about. Got a story? We want to hear it. Drop it in the comments or share it in your podcast app. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-find-more-luck-with-your-money-1749 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 7 mins
  • How to Deliver the “WOW” in Everyday Life (with longtime former Royal Caribbean Chairman and CEO Richard Fain) SB1748

    How to Deliver the “WOW” in Everyday Life (with longtime former Royal Caribbean Chairman and CEO Richard Fain) SB1748
    Oct 15 2025
    You don’t have to command a cruise ship (or a boardroom) to lead with purpose. On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome Richard Fain, longtime chairman and former CEO of Royal Caribbean Group, for a conversation that’s not about corporate leadership… but about life leadership. Richard shares timeless lessons he learned from decades steering one of the world’s most innovative companies—lessons that apply just as powerfully to parenting, coaching your kid’s soccer team, running a PTA fundraiser, or simply trying to create more joy at home. You’ll hear how to dream bigger about your own life, build a culture of kindness and excellence in small groups, and turn the ordinary moments around you into opportunities to “deliver the WOW.” Of course, this wouldn’t be the basement without a few money detours. The crew also breaks down new 401(k) rules and annuity updates, debates whether tax flexibility beats fancy planning, and celebrates Doug’s birthday with trivia, laughter, and a few movie reviews along the way. By the end, you’ll walk away inspired to bring a little more vision, creativity, and generosity into every corner of your world. No cruise ship required. What You’ll Learn How to lead from wherever you are: Richard’s lessons on building strong teams, communities, and families. No corner office needed. Turning the ordinary into extraordinary: Simple ways to “deliver the WOW” at home, work, or anywhere people count on you. Dreaming bigger about your life: Why bold vision isn’t just for CEOs; it’s for anyone looking to create meaning and momentum. Financial updates you can use: New 401(k) rules, annuity insights, and practical tips to strengthen your plan. The lighter side of leadership: Trivia, birthday celebrations, and a few fun detours (because we can’t resist). Questions for the Basement What’s one way you could “deliver the WOW” in your own life this week? Who’s a leader in your everyday world (at home, work, or your community) who’s made an impact on you? How can dreaming a little bigger change the way you approach your next financial or personal goal? FULL SHOW NOTES: https://stackingbenjamins.com/better-money-habits-with-richard-fain-1748 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 12 mins