The Stacking Benjamins Show

• Banishing Money Monsters: How to Talk Money With Anyone (Partners, Roommates, or Coworkers) SB1754

  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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• Real Money Horror Stories (And How Not to Star in Your Own) SB1753

  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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• You've Got Enough Money to Quit. Should You? SB1752

  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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• Your Money Problems Aren't Math Problems (They're People Problems) SB1751

  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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• Should You Drain Your Emergency Fund? (And 4 Other Money Questions Keeping You Up) SB1750

  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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