The Stacking Benjamins Show

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 [https://www.StackingBenjamins.com/201] Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

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 [https://www.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 [https://www.stackingbenjamins.com/201] Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

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 [https://stackingbenjamins.com/voicemail] FULL SHOW NOTES: https://stackingbenjamins.com/answering-your-burning-financial-questions-1750 [https://www.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 [https://www.stackingbenjamins.com/201] Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

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 [https://www.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 [https://www.StackingBenjamins.com/201] Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

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 [https://www.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 [https://www.stackingbenjamins.com/201] Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]