The Stacking Benjamins Show

What if you could sit down with the people actually building the future of personal finance and just... ask them everything? That's exactly what happens in this episode. Joe Saul-Sehy gathers three FinTech insiders around the basement table—Peter Polson (founder, Tiller), Aaron Froug (founder, Grifin), and Ryan Ruff (longtime FinTech pro, Array)—for a rare look inside the industry that's reshaping how we handle money. This isn't about pitching their products. It's about understanding how FinTech actually works, where it's headed, and how everyday people can use these tools more effectively. Peter and Aaron share what they've learned building companies from the ground up, while Ryan pulls back the curtain on the infrastructure most people never see but rely on every single day. The conversation goes deep: What are most people getting wrong about money apps? How can you get more value from the tools you're already using? Where is AI actually making finance easier (versus just adding complexity)? And as creators, how can they design tools that genuinely help people instead of just creating more digital clutter? You'll also hear their take on what's coming next—the innovations that'll matter in five years, the trends that are overhyped, and the blind spots the industry still needs to address. Whether you're a FinTech skeptic or an early adopter, this conversation will change how you think about the apps sitting on your phone right now. What You'll Walk Away With: • The insider perspective on how FinTech tools are actually designed—and what builders wish users understood • How to get more value from the financial apps you're already using (most people only scratch the surface) • Where the industry is headed: what innovations are real and what's just hype • Why some tools work for some people but fail for others—and how to find your fit • The infrastructure that makes your financial apps work (and what breaks when it doesn't) • How AI is changing personal finance in practical ways, not just buzzword ways • What FinTech creators are trying to solve—and where they admit the industry still falls short This Episode Is For You If: • You're curious about what's actually happening inside the FinTech world • You want to use your money apps smarter, not just download more of them • You're wondering what's coming next in personal finance tech and whether it'll actually help • You've felt like financial tools are being built for someone else, not for you • You want the insider perspective without the sales pitch—just honest conversation from people who live this every day Before You Hit Play, Think About This: What's one thing you wish your money apps could do better? Drop it in the comments—these are exactly the kinds of insights that help creators build tools that actually work for real people. FULL SHOW NOTES: https://www.stackingbenjamins.com/the-current-state-and-future-of-fintech-1764 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

Be honest: When someone's talking to you, are you actually listening—or just waiting for your turn to speak? Joe Saul-Sehy and OG welcome executive coach Katie O'Malley, who's here to expose how terrible most of us are at paying attention—and more importantly, how to fix it. Whether you're trying to connect with your spouse, navigate a tough conversation with your kid, or just survive Thanksgiving dinner without the crypto uncle derailing everything, Katie's got the framework that makes you a better listener (and weirdly, a better decision-maker too). Here's the thing: better listening doesn't just improve your relationships. It improves your money decisions. When you're actually present instead of distracted, you catch the details that matter. You ask better questions. You make choices that align with your values instead of reacting on autopilot. Katie breaks down the reflective listening technique that changes every conversation—at work, at home, and yes, even about money. Joe and OG also dig into financial literacy for younger Stackers (because the skills you wish you'd learned earlier are the ones you should be teaching now), plus new research on all-stock portfolios and whether they're brilliant or just reckless depending on your risk tolerance. And Doug? Doug's got Halloween-adjacent music trivia and commentary that reminds you not everything needs to be taken seriously. What You'll Walk Away With: • The reflective listening framework that immediately improves how you communicate (with everyone) • Why "listening to respond" instead of "listening to understand" sabotages your conversations • Simple techniques to break free from distraction loops—especially the ones involving your phone • How better communication leads to better financial decisions (they're more connected than you think) • What the research actually says about all-stock portfolios and whether they fit your risk tolerance • Ways to teach young people the financial skills they need—even if nobody taught you • Strategies for staying present during stressful family moments (holiday season, we see you) Before You Hit Play, Ask Yourself: • When was the last time you listened to understand instead of just waiting for your turn to talk? • What relationships in your life would improve if you were actually present instead of mentally writing your grocery list? • Are you teaching the young people in your life the money skills you wish someone had taught you? • Does your investment strategy match your actual risk tolerance—or just what sounded good on TikTok? • What uncomfortable conversations are you avoiding because you don't know how to navigate them? Got a communication breakdown you're trying to fix—financial or otherwise? Drop it in the comments. The basement's got your back. 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

Pop quiz: If your health insurance premiums keep climbing, should you just go catastrophic and pocket the savings? Joe Saul-Sehy, OG, and CFP Anna Allem tackle that exact question, along with a handful of other money decisions that keep Stackers up at night. From navigating healthcare coverage gaps to figuring out when (and how) to withdraw from a 529, this Monday mailbag episode is packed with the practical advice you need, served with the basement humor you've come to expect. The health insurance conversation gets real: what catastrophic plans actually cover (spoiler: less than you think), how to plan for the gaps, and whether gambling on your health is ever a smart financial move. Then Anna breaks down the 529 withdrawal strategy that saves you headaches at tax time, and the crew tackles a listener who's spooked by market volatility and wondering if it's time to bail. But it wouldn't be Monday without some chaos—Joe's cat decided to add drama to the morning, Doug brings trivia about counterfeit currency (because of course), and the gang updates you on the charity challenge where Stackers can support financial literacy and maybe win some prizes in the process. Plus: OG delivers movie reviews to help you figure out what's actually worth your streaming time this week. What You'll Walk Away With: • The truth about catastrophic health plans—when they make sense and when they'll leave you exposed • How to handle healthcare coverage gaps without gambling your financial future • The smart way to withdraw from a 529 so you don't accidentally trigger taxes or penalties • Why market volatility isn't a reason to panic—and what to do instead of bailing on your portfolio • How diversification and rebalancing keep you sane when the headlines get scary • A reminder that financial planning (like cat wrangling) rarely goes exactly as planned This Episode Is For You If: • You're staring at rising health insurance premiums and wondering if there's a better way • You've got a 529 but aren't sure how to actually use it without screwing up • Market dips make you nervous and you want to know if you should be doing something • You're tired of generic financial advice and want real answers to your specific questions • You believe learning about money should involve at least a few laughs (and maybe some cat stories) Got a Question for the Basement? Drop it in the comments or send it our way—you might just hear Joe Saul-Sehy, OG, and Anna tackle it in an upcoming mailbag episode. And if you want to support financial literacy while competing for prizes, check out the charity challenge details in the show. 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

Ever feel like you're doing everything "right" with money—but still barely getting ahead? You're budgeting. You're saving what you can. You cut the subscriptions, meal prep on Sundays, and skip the daily latte. So why does it still feel like you're spinning your wheels? In this Greatest Hits episode, Joe Saul-Sehy welcomes Erin Lowry (Broke Millennial), Paula Pant (Afford Anything), and Greg McFarlane (Control Your Cash) to tackle the question nobody wants to ask: What if the problem isn't your spending—it's your income? Erin shares her journey from broke and stressed to financially stable and empowered, and the crew digs into why so many families struggle even when they're following all the "rules." Sometimes extreme budgeting isn't the answer. Sometimes you need to earn more. And yes, that's easier said than done—but this episode gives you the roadmap. From practical strategies for saving for retirement when cash is tight, to negotiation tricks that lower your monthly bills, to the hilariously strange side hustles people actually do for extra money (you'll never look at classified ads the same way), this conversation is packed with ideas you can use today. Plus: Classic basement banter, a "Spider Pig" serenade, Tony Romo's birthday, and all the tangents that make Stacking Benjamins feel like hanging out with friends who happen to know a lot about money. What You'll Walk Away With: • Why you might feel behind even when you're doing everything the experts tell you to do • Erin Lowry's framework for moving from "broke" to financially confident (and why it's not just about willpower) • When to focus on cutting costs vs. when to focus on earning more—and how to know the difference • Practical retirement savings strategies that work even when your cash flow is tight • Negotiation scripts for lowering your internet, phone, and other monthly bills (yes, they actually work) • Creative (and sometimes bizarre) ways people make extra money that you've probably never considered This Episode Is For You If: • You're exhausted from budgeting and feel like you're sacrificing everything but still not getting ahead • You wonder if you're just bad with money—or if something else is going on • You've cut expenses as far as they'll go and need new strategies • You're curious about side hustles but don't know where to start (or what's actually worth your time) • You need a reminder that struggling financially doesn't mean you're doing it wrong—sometimes the system is just rigged FULL SHOW NOTES: https://stackingbenjamins.com/stop-worrying-start-saving-greatest-hits-week-1761 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

Here's what nobody tells you about building wealth: it's not about finding the perfect investment or timing the market. It's about doing boring things consistently until they're not boring anymore—they're just your life. In this Greatest Hits episode, Joe Saul-Sehy and OG revisit a 2023 conversation with Jonathan Clements, the beloved former Wall Street Journal personal finance columnist and founder of Humble Dollar who passed away recently. We're resharing this episode to honor Jonathan's legacy, his gift for making complex ideas simple, and the joy he brought to every conversation about money. Jonathan's book, My Money Journey, features 30 real stories from real people who built financial freedom—and the lessons are surprisingly simple (which doesn't mean easy). In this conversation, Jonathan breaks down what separated the people who made it from the people who kept spinning their wheels: steady habits, ruthless simplicity, and the kind of resilience that lets you keep going when life throws curveballs. From emergency funds that actually saved people to the rent vs. buy debate that reveals more about your priorities than your budget, this conversation cuts through the complexity to show you what actually matters. Jonathan's wisdom feels even more valuable now—a reminder that the best financial advice isn't about chasing trends, it's about building a life that works for you. Joe and OG also tackle listener questions, including whether to relocate for a better job and how to balance saving for tomorrow without sacrificing today. Plus: Doug's trivia, a Key & Peele-inspired TikTok minute, and proof that the best financial teachers leave lessons that last long after they're gone. What You'll Walk Away With: • The money habits that showed up in almost every success story from Jonathan's book (spoiler: none of them are sexy) • Why simplicity beats complexity in investing—and how to stop overcomplicating your portfolio • The rent vs. buy question reframed: it's not just about math, it's about what kind of life you want • How to balance aggressive investing with the safety net you actually need (not the one Instagram tells you to have) • Why emergency funds and health insurance are the unsexy heroes of every financial success story • What "margin for error" really means—and why it's the difference between surviving setbacks and being destroyed by them This Episode Is For You If: • You're tired of chasing the next "hot" investment strategy and want to know what actually works • You feel like everyone else has figured out money except you (spoiler: they haven't) • You want to hear real stories from real people, not just theory from talking heads • You're trying to balance living well now with saving for later—and feeling stuck in the middle • You believe the best teachers are the ones whose lessons outlive them 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

Here's a wild idea: What if the thing holding you back isn't your bank account, your age, or your circumstances—it's just the story you've been telling yourself? Joe Saul-Sehy and OG sit down with Colin O'Brady, four-time world record holder and endurance athlete who's done things most people would call impossible: solo trek across Antarctica, row across the Drake Passage, and yes, take a 12-hour walk that changed his entire perspective on what humans are capable of. Colin's not just here to tell adventure stories (though those are incredible). He's here to talk about the mental game—the part where you convince yourself to take the first step even when the finish line seems impossibly far away. Sound familiar? Whether you're staring down a cross-country expedition or trying to figure out if you'll have enough saved for retirement, the challenge is the same: push past the voice that says "I can't" and prove to yourself that you can. Then Joe and OG bring it back to the basement with a listener question about Roth vs. Traditional 401(k) contributions—because financial endurance is just as important as physical stamina. They break down how to think long-term about taxes, flexibility, and building a retirement plan that actually fits your life. Plus: Neighbor Doug delivers trivia that proves even world record holders have to earn their laughs in the basement. What You'll Walk Away With: • What Colin O'Brady's 12-Hour Walk reveals about breaking through your mental limits (and how it applies to money decisions too) • The mindset shift that separates people who attempt big goals from people who actually achieve them • Smart strategies for balancing Roth and Traditional 401(k) contributions based on your timeline and tax situation • Why flexibility matters as much as discipline—whether you're planning an expedition or planning retirement • Permission to set goals that scare you a little (because that's usually where the good stuff happens) This Episode Is For You If: • You've been telling yourself you "can't" do something but wonder if that's actually true • You want inspiration that comes with actual tactics (not just motivational fluff) • You're trying to figure out the Roth vs. Traditional 401(k) question and want a clear answer • You believe your best life is out there, but you're not sure how to build toward it • You need a reminder that big transformations start with small, intentional steps FULL SHOW NOTES: https://stackingbenjamins.com/conquer-your-mount-everest-greatest-hits-week-1759 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

Want to know what keeps retirees up at night? It's not what they did—it's what they wish they'd done ten years earlier. Joe Saul-Sehy is joined by Jill Siriani (Frugal Friends), Jesse Cramer (The Best Interest), and Doc G (Earn & Invest), who all pull up chairs in the basement for a powerhouse roundtable on the five regrets that show up again and again when people hit retirement. These aren't hypothetical "what-ifs"—they're real stories from a real CFP, sharing tales about people who wished someone had told them sooner. From botched investment allocations that left people either too risky or too conservative, to tax mistakes that cost tens of thousands, to the heartbreaking pattern of people who saved everything but never actually enjoyed their money—this conversation gets real about what actually matters when you're trying to retire with confidence (and joy). The good news? Every single one of these regrets is avoidable. The panelists share what to do now so you don't become one of these stories later, including the estate planning moves that take ten minutes but save your family years of headaches, and why the biggest retirement regret isn't financial at all—it's emotional. Plus: Doug's trivia challenge pits the panel against each other for bragging rights, because even serious money talk deserves a little competition. What You'll Walk Away With: • The five regrets that show up over and over in retirement—and the specific moves that prevent each one • Why your investment allocation in your 40s and 50s might be setting you up for regret in your 60s • Tax strategies that keep more money in your pocket (because giving Uncle Sam extra is nobody's retirement dream) • The simple estate planning steps most people skip—and why your family will thank you for not skipping them • How to give yourself permission to actually enjoy your money instead of hoarding it out of fear This Episode Is For You If: • You're decades from retirement but want to avoid the "I wish I'd known" moments • You're closer to retirement and worried you've missed something important • You want to hear top financial minds debate what actually matters (spoiler: they don't always agree) • You're tired of generic retirement advice and want to hear what real retirees actually regret • You believe retirement should be about living well, not just having enough FULL SHOW NOTES: https://stackingbenjamins.com/top-5-retirement-plan-regrets-1758 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

Here's a question: If everyone's buying annuities right now, does that mean you should too? Joe Saul-Sehy, OG, and Neighbor Doug tackle that exact question in this week's episode—but first, they're starting with the basics. Because before you can figure out complex financial products, you need to nail the fundamentals. And who better to teach them than Karen Holland, founder of Gifting Sense, who's made it her mission to help kids (and their parents) understand money in ways that actually stick. Karen breaks down how to teach the next generation about "need vs. want," why middle schoolers need to understand the real cost of "cool," and how financial literacy can be empowering instead of intimidating. Whether you've got kids or just want a refresher on the money basics you wish someone had taught you, this conversation is the reset button you didn't know you needed. Then things get timely: annuity sales are booming, and everyone's suddenly got an opinion. But are annuities the safe harbor they're marketed as, or just another way to lock up your money with fees you don't understand? Joe and OG cut through the sales pitch to help you figure out when annuities make sense—and when you're better off walking away. Plus: Doug delivers "life-changing" trivia (his words), there's an iHeart Music Festival giveaway tied to financial literacy, and you'll get your weekly dose of basement wisdom served with laughs. What You'll Walk Away With: • Karen Holland's framework for teaching kids financial literacy that actually changes behavior (not just lectures that go in one ear and out the other) • Why annuity sales are exploding right now—and the questions you MUST ask before signing anything • The difference between annuities that solve real problems and annuities that just create expensive ones • Financial habits that work at any age—whether you're teaching a 12-year-old or retraining yourself • How supporting financial education can score you iHeart Music Festival tickets (because doing good shouldn't be boring) This Episode Is For You If: • You want to teach kids about money but don't know where to start (or worry you'll mess it up) • Someone's pitched you an annuity and you're not sure if it's brilliant or a trap • You've heard annuities are "safe" but want to understand what you're actually giving up • You believe financial literacy is a gift worth giving—to your kids, your community, or yourself • You want money advice that doesn't talk down to you or assume you already know everything FULL SHOW NOTES: https://stackingbenjamins.com/raising-money-for-financial-literacy-1757 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

Nobody plans for their finances to get tight. But here you are, staring at your bank account, wondering if you should panic now or wait until next Tuesday. Joe Saul-Sehy, OG, and Neighbor Doug are here to talk you off the ledge—and give you an actual plan for when money gets squeezed. Whether you're facing a layoff, dealing with reduced hours, bracing through a government shutdown, or just trying to make your paycheck last until payday, this episode is your financial storm shelter. The good news? You don't need to have everything figured out perfectly to make it through. You just need to know what to do first, what can wait, and how to keep your head (and your budget) together when everything feels uncertain. From building an emergency fund that actually works for your life to eating well on a ramen budget (spoiler: it's possible), this crew breaks down the practical moves that keep you afloat. Plus: Doug delivers trivia, the gang tackles the Voices for Good Charity Challenge (because even in tough times, small acts of giving matter), and they dissect a TikTok money tip that's... well, let's just say not all financial advice should be followed. What You'll Walk Away With: • The first three moves to make when money gets tight—before the panic spiral starts • How much emergency fund you actually need (hint: it's probably less than you think to get started) • Budget-friendly tactics for groceries, utilities, and keeping yourself fed without living on instant noodles • What to do about insurance and loans when cash flow slows down (and which mistakes cost you later) • Why small acts of generosity matter even when you're struggling—and how they help you too • A reminder that financial storms are temporary, but the skills you build weathering them last forever This Episode Is For You If: • Money feels tighter than it used to and you're not sure what to do about it • You want to build a safety net but don't know where to start (or how much is "enough") • The economy feels shaky and you want to feel prepared instead of panicked • You're tired of generic advice like "just save more" and want actual tactics • You need a pep talk wrapped in practical wisdom—because optimism without a plan isn't helpful FULL SHOW NOTES: https://stackingbenjamins.com/the-importance-of-emergency-funds-1756 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

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

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

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

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

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

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

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

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

Here's a rewritten version of your “Gold Prices Hit All-Time Highs (What's That Mean To Us?)” show notes — polished for clarity, SB voice, and listener engagement, with your established tone and avatar in mind: When gold shines, so do the hot takes—and today, the Stacking Benjamins crew dives into what this record-breaking surge really means for your money. Joe Saul-Sehy, OG, and Neighbor Doug kick off the week with their signature Monday salute to our troops before digging into the glittering headlines: gold prices are hitting new highs… but does that make it a smart investment or just financial fool's gold? From breaking down why gold spikes when markets wobble to questioning whether it's truly the “safe haven” it's cracked up to be, the guys unpack the myths, mindset, and math behind precious metals. You'll also hear fresh strategies for weathering volatile markets, balancing your asset allocation, and staying cool when everyone else is panicking. And of course, Doug drops in with a TikTok Minute, a trivia challenge, and one listener's wild math-powered success story that somehow involves an Olive Garden. (Breadsticks optional.) So grab your coffee, your calculator, and maybe your lucky coin—because this episode proves that in the unpredictable world of investing, sometimes the smartest move is knowing why you're holding what you're holding. What You'll Learn Why gold prices are climbing and what that might signal about the global economy. The myth of “safe haven” assets: When gold works, when it doesn't, and why diversification still wins. Smart portfolio moves for volatile times—without letting emotions tank your returns. Real-life stories and lessons from Stackers proving that good math (and a little luck) can go a long way. The lighter side of finance: Breadsticks, TikTok, and trivia—because learning about money doesn't have to feel like homework. Questions You'll Want to Answer: Do you view gold as an investment, insurance policy, or just a shiny distraction? What's your go-to strategy when markets start getting rocky? Have you ever made a “safe” financial move that didn't turn out as safe as you thought? FULL SHOW NOTES: https://stackingbenjamins.com/gold-and-other-investments-for-bear-markets-1747 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

Who says you have to wait until 65 to clock out and start living your best life? On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, Paula Pant (Afford Anything), OG, and special guest Sean Mullaney—author, CFP®, and early retirement strategist—explore how to design a life that lets you walk away from the office sooner and happier. From tax-smart withdrawal strategies to dialing in your lifestyle design, this conversation pulls back the curtain on what it really takes to achieve early financial independence. You'll hear practical steps for aligning your money with your values, structuring your investments for flexibility, and ensuring your plan can survive market dips and surprise expenses. Along the way, the team debates Roth vs. Traditional retirement accounts, shares personal insights from FinCon, and delivers a few laughs (and groans) in Doug's trivia corner. Whether you're in your 30s planning a slow exit or in your 50s wondering if it's too late to pivot, this episode is your guide to crafting a retirement plan that works as hard as you do—without losing sight of the joy along the way. What You'll Learn How to design your early retirement plan: The building blocks of lifestyle design and financial freedom. Tax-efficient investing: When to prioritize Roth vs. Traditional accounts—and why both can play a role. Withdrawal strategies that work: How to avoid tax traps and keep your plan sustainable. The mindset shift: Why retiring early isn't about leaving work—it's about moving toward purpose. How to “future-proof” your finances: Guarding against inflation, longevity risk, and unexpected curveballs. Questions to Ponder During Today's Show: What would your perfect day look like if you didn't have to work tomorrow? Would you be willing to earn less now if it meant retiring five years earlier? What does “enough” look like for you—and how do you know when you've reached it? FULL SHOW NOTES: https://stackingbenjamins.com/building-your-early-retirement-plan-1746 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

What if building wealth wasn't just about stacking dollars — but also stacking good deeds? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG sit down with Mel Dorman, a powerhouse real estate investor who turned humble beginnings (yes, dumpster diving beginnings) into a thriving portfolio of 34 rental units in just five years. And she didn't just build wealth — she built community along the way. From negotiating creative seller-financed deals to forging partnerships that benefit both investors and neighborhoods, Mel shares how real estate can be a tool for connection as much as for cash flow. You'll learn how she leverages relationships, uses alternative financing to scale quickly, and even flips properties without traditional bank loans — all while staying grounded in her mission to help others. But that's not all: Joe and OG also break down the latest Federal Reserve moves and what they mean for your wallet. And of course, Neighbor Doug drops by with his signature trivia to remind us that building wealth is serious business… but it's okay to have some fun while you're at it. What You'll Learn Creative ways to build wealth: How seller financing can unlock deals you never thought possible. The power of purpose: Why combining community impact with real estate investing is a winning formula. Real-world strategies: Mel's journey from zero to 34 units — and the lessons she learned along the way. How Fed rate changes affect you: What rising (or falling) rates mean for investors and homeowners. Financing myths busted: Why traditional bank loans aren't the only way to grow a portfolio. Points to Ponder: Could creative financing open doors for your investing goals? How might building stronger community ties improve your financial outcomes? Are you prepared for how interest rate changes could impact your next big money move? This episode isn't just a guide to real estate success — it's a reminder that money works best when it works for everyone. Grab a notebook, pour yourself something caffeinated, and join us for a conversation that just might change how you think about wealth building. FULL SHOW NOTES: https://stackingbenjamins.com/real-estate-investing-in-your-community-1745 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

What if the key to a richer life isn't about chasing the next hot stock or grinding harder — but learning to master the timeless truths of money? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug pay tribute to legendary financial writer Jonathan Clements by revisiting five of his most impactful lessons. These aren't complicated formulas or secret hacks — they're the kind of deceptively simple ideas that change the way you think about money, work, and what truly matters. We'll explore why prioritizing financial stability before passion can actually lead you to a more fulfilling career, how “winning by not losing” may be the most underrated investing strategy of all time, and why patience isn't just a virtue — it's a tax strategy. Along the way, we'll talk about how to strike the right balance between frugality and joy and why living your life may be the best investment you ever make. Plus, we help Stacker Kat tackle a tricky severance situation and share tips on how to put that cash to work without capsizing your financial plan. If you've ever wondered how to align your money with a life you actually love, this conversation is the perfect mix of inspiration and actionable wisdom. Grab your coffee mug and settle into Mom's basement — this is an episode you'll come back to whenever you need a financial reset. What You'll Learn The real reason you shouldn't chase passion too soon — and what to do instead How to avoid the most common (and costly) financial mistakes Why patience pays: how time turns taxes into opportunity How to balance frugality with actually living a fulfilling life Smart ways to use severance, high-yield savings, and investing strategies together Points To Ponder: Which of Jonathan Clements' five money lessons hits closest to home for you? Have you ever faced a tough severance decision like Stacker Kat's? What did you do? Do you believe financial stability should always come before passion — or is there a time to flip that script? FULL SHOW NOTES: https://stackingbenjamins.com/five-pearls-of-wisdom-from-jonathan-clements-1744 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

If your financial plan feels more like a vague wishlist than a real roadmap, this episode is about to change that. Live from the basement of YouTube HQ, Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long-Term Investors) roll up their sleeves and dig into the three most common — and costly — mistakes people make with their money plans. Whether you're just starting out or you've been stacking for years, this conversation will help you turn “someday” into a solid plan you can actually follow. The gang isn't just talking theory — they're breaking down the real reasons plans fail and how to fix them. From adding actionable next steps (instead of endless spreadsheets and good intentions) to weaving in crucial tax and estate planning moves, you'll discover how to transform your financial plan into a tool that works for you. And because this is Stacking Benjamins, you can expect plenty of banter, relatable stories, and a trivia detour or two along the way. By the time we wrap, you'll know how to evaluate whether your plan is truly moving you toward your goals, how to communicate more effectively with your financial pros, and how to stop second-guessing every decision. It's financial planning with fewer headaches, more confidence, and maybe even a little fun. What You'll Learn Why most financial plans fail — and how to make yours bulletproof The three crucial elements every solid plan needs (and most are missing) How to incorporate tax strategies, estate planning, and real action steps Smart ways to communicate with your advisor or team about what matters most Questions to Consider How to course-correct if your plan's gone off the rails Does your financial plan include clear, actionable steps — or just big goals? Have you factored in tax and estate planning, or are you leaving those to chance? Are you confident your plan will work in real life, not just on paper? FULL SHOW NOTES: https://stackingbenjamins.com/three-things-missing-from-most-financial-plans-1743 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

Think your retirement plan is bulletproof? Think again. In this eye-opening episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by certified financial planner Jeremy Keil, CFP® to walk you through the steps to building a retirement plan that won't crack under pressure. From mapping out your spending before you ever leave the workforce to crafting a tax strategy that keeps more money in your pocket, this conversation is your blueprint for making your golden years actually golden. But just when you think you've got retirement handled, we throw a curveball: private equity. With giants like Goldman Sachs and T. Rowe Price trying to slip these complex investments into your 401(k), it's time to ask whether “more opportunity” is really a good thing — or a trap for the unprepared. Joe and OG break down the risks, the realities, and what you need to know before you sign on the dotted line. As always, we serve it all with a side of basement banter — from Doug's trivia about the first issue of Playboy to a TikTok football moment you didn't know you needed — plus real-life stories that prove retirement planning is as much about mindset as it is about math. What You'll Learn In Today's Show: The five key steps to building a retirement plan that works for you, not just a generic spreadsheet. Why starting with your spending habits (not investments) can make or break your retirement success. How to prepare for the emotional side of retirement — including those pesky “what now?” questions. The surprising risks of private equity creeping into your 401(k) — and how to decide if it's worth it. Smart tax strategies to make your retirement money last longer. How long-term care, market volatility, and unexpected expenses should factor into your plan. Questions to Ponder During the Episode (and discuss with other Stackers!) What's one spending habit you need to understand now to avoid retirement surprises later? How would you react if your employer added private equity options to your 401(k)? Are you planning your retirement based on your lifestyle — or someone else's idea of “enough”? FULL SHOW NOTES: https://stackingbenjamins.com/five-steps-to-a-better-retirement-plan-with-jeremy-keil-1743 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

Think the American Dream is slipping out of reach? Think again. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug tackle one of the biggest financial questions of our time: how much does it really cost to live the life you want — and is it still possible? Spoiler alert: it is, but it takes more than a paycheck and a Pinterest board. We break down fresh research from Investopedia, the rising price tag of everything from healthcare to college, and how smart planning (and a little basement wisdom) can keep your dreams from turning into financial nightmares. But this isn't just another numbers game. Along the way, the gang shares stories from the road — including Joe's brush with baseball's most entertaining team — and digs into the strategies that can help you fight inflation, outsmart rising costs, and make compounding interest your best friend. Plus, we tackle big listener questions, from how to choose the right financial advisor to the best ways to set young adults up for success in a tougher economic landscape. And because life isn't all spreadsheets and savings goals, we round things out with some binge-worthy TV and movie picks for when you're off the clock. It's part money masterclass, part basement hangout — and all about helping you take real steps toward your version of the American Dream. What You'll Learn in This Episode Why the “American Dream” isn't dead — but why it may look different today. The real costs behind homeownership, healthcare, education, and retirement (and how to plan for them). Strategies for budgeting, saving early, and building systems that make your money work harder. How to vet a financial advisor and what red flags to watch out for. Smart ways to guide young adults toward financial independence. The power of compounding interest and how to use it to your advantage. Questions to Consider (and Discuss with Fellow Stackers) What does the “American Dream” mean to you — and has that definition changed over time? Which costs (housing, healthcare, college, etc.) feel most overwhelming right now, and how are you tackling them? What's one piece of financial advice you'd give to someone just starting their journey? FULL SHOW NOTES: https://stackingbenjamins.com/the-rising-cost-of-the-american-dream-1741 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

What if tweaking just a few “knobs” in your 401(k) could mean the difference between retiring with confidence or wondering if you'll ever stop working? In this spirited episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by three of our favorite money minds — Paula Pant from AffordAnything, Jesse Cramer from Personal Finance For Long Term Investors, and Lacey Langford from The MILMO Show — to break down everything you thought you knew (and a few things you probably didn't) about retirement planning. From the basics of employer matches and contribution strategies to the great Roth vs. Traditional debate, we're exploring the smart moves that can supercharge your 401(k) — and the missteps that can quietly drain your future nest egg. Along the way, you'll pick up clever tips, a few head-scratching stories, and some beer-fueled trivia that will leave you laughing harder than your HR rep when you ask if “401(k)” is the Wi-Fi password. And because this is Stacking Benjamins, the conversation goes far beyond just investment allocations and tax advantages. We dig into why behavioral traps can derail your savings plan, how military families can maximize their benefits, and why understanding fees is one of the most underrated wealth-building moves you can make. So grab a pretzel, pull up a chair, and let's talk about how to make your money work harder — so future you can kick back with a stein and say, “I nailed this retirement thing.” How to “tune” your 401(k) like a pro — from employer matches to smart contribution strategies. The real differences between Roth and Traditional accounts (and how to decide which is right for you). Why understanding your 401(k) fees could add thousands to your future balance. How military families can make the most of unique retirement benefits. The biggest mistakes people make with their 401(k)s — and how to avoid them. Plus: A special Oktoberfest-themed trivia showdown and plenty of basement banter. FULL SHOW NOTES: https://stackingbenjamins.com/tweaking-your-retirement-account-1740 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

What if the secret to enjoying your job isn't grinding harder but stepping back and rethinking how work fits into life? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome special guest Shemin Nurmohamed to unpack the Paris Paradox: balancing work and leisure without sacrificing ambition. From cultural perspectives on downtime to the productivity perks of unplugging, Shemin shows why working less might just help you accomplish more. But that's not all. What happens when your financial advisor suddenly jumps ship to another firm? The team digs into what it means for your money, your relationship with your advisor, and how to evaluate whether it's time to follow—or finally shop around. Add in Doug's trivia, a few stumbles down random rabbit holes, and our community's contributions, and you've got a lively mix of practical advice and classic basement energy. Whether you're plotting your next vacation or just trying to figure out how to stop your inbox from running your life, this episode offers real-world strategies (and plenty of chuckles) to help you reset, recharge, and refocus. Why time off is not laziness but fuel for better work and sharper decision-making. How cultural differences around leisure can reshape your own approach. What to do when your advisor changes firms (and how to spot a keeper). Practical ways to build stronger connections and communities. The “Two Beers and a Puppy” test: a surprisingly effective tool for evaluating relationships. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-work-less-live-more-and-love-your-job-1739 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

Ever make a money move in the heat of the moment and wish you could take it back? That's exactly why a rock-solid Investment Policy Statement (IPS) might be your most underrated financial tool. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug peel back the layers on IPSs—why they matter, how they save you from your own impulses, and the role they play in making sure your investment strategy actually sticks. Think of it as your financial GPS, keeping you on course when market turbulence makes you want to grab the wheel. But it's not just about avoiding panic-selling. The basement crew digs into the nuts and bolts of what a good IPS should include, from setting specific goals to handling liquidity needs and keeping your risk tolerance aligned with your lifestyle. You'll also hear how rebalancing, governance, and regular reviews can transform your investments from “hope and pray” into a system you can rely on. Along the way, expect the usual SB tangents: a Joan Jett–themed trivia challenge, a TikTok tale about Apple Pay gone wrong, and more than a few moments where Doug forgets he's not supposed to run the show. By the end, you'll not only understand how to create (or update) your IPS, but you'll also see how it connects directly to building confidence in your financial plan. Whether you're brand new to investing or a seasoned hand looking to sharpen your strategy, this episode delivers the blueprint. Why an Investment Policy Statement is your best defense against emotional investing How to set clear goals, liquidity rules, and risk guidelines for your portfolio The pitfalls most people overlook when drafting an IPS (and how to avoid them) Smart strategies for rebalancing and reviewing your plan without overcomplicating things A cautionary tale from TikTok that reminds us all to keep our guard up with payment apps Listener Q&A on stock sales and the quirks that come with them Questions You'll Begin to Answer During the Episode: Do you have a written IPS, and if so, does it reflect your actual goals—or just what you thought they were five years ago? What emotional triggers most often tempt you to stray from your financial plan? How often do you review your investments, and is it based on strategy—or headlines? FULL SHOW NOTES: https://stackingbenjamins.com/simple-steps-for-better-money-management-1738 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

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

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

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

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

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

Not all financial advisors are created equal—and some will steer you straight into the rocks while smiling the whole way. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug share the top five warning signs your advisor may not have your best interests at heart. From shady investment recommendations to fee structures that deserve a magnifying glass, we unpack the behaviors and practices that can quietly drain your portfolio. This isn't just about avoiding bad actors—it's about knowing what great advice looks like so you can spot the difference. You'll hear why “fun money” accounts can be a trap, how to sniff out overly speculative pitches, and why transparency isn't optional when it comes to your financial future. Along the way, we sprinkle in a few stories, historical nuggets, and plenty of those classic “Doug moments” that make a trip to the basement worth your time. If you've ever wondered whether your financial guide is truly on your side—or if you just want to sharpen your radar—this episode will give you the practical tools to tell the difference between a trusted partner and a wolf in a well-tailored suit. What You'll Learn in This Episode The five biggest advisor red flags that should send you running How to evaluate an advisor's investment recommendations for risk and suitability Why fee transparency can make or break a relationship The subtle clues in an advisor's office environment and interactions The difference between fun money accounts and dangerous speculation How to ensure your advisor's plan matches your long-term goals Questions to Think About: When's the last time you reviewed exactly how your advisor gets paid? Are you clear on the why behind each investment they've recommended? Would you feel confident explaining your advisor's strategy to a friend—or does it sound like a foreign language? This episode originally aired on August 2, 2023. Please disregard any mention of current events. You can find the original show notes here. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-spot-a-subpar-advisor-greatest-hits-week-1732 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

Ever celebrate paying off a credit card…only to watch your credit score drop? Or ditch your budget for “simplicity” and find yourself ordering takeout three nights in a row? On this week's episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome Paula Pant (Afford Anything) and Jesse Cramer (Personal Finance for Long-Term Investors) to explore why even the “right” financial moves can sometimes lead you straight into a banana peel. From the hidden traps of credit scores and debt freedom to the way a shiny new credit card reward program can cost you more than you bargained for, this roundtable digs into the ripple effects that don't make the brochure. We'll tackle when “optimizing” your plan goes too far, how well-meaning programs can backfire, and why the metric you're tracking might not be the one that actually matters. Expect sharp insights, lively debate, and tips you can put into action—without getting tangled in the very strategies meant to help you. Because money confidence isn't just about making the right moves…it's about knowing what those moves might do next. We'll Cover: Why your credit score might drop after paying off debt—and why that's not always bad news How “budget hacks” can turn into budget headaches The sneaky ways credit card rewards and government programs can backfire Why tracking the wrong measure can lead to the wrong results Practical steps to sidestep the unintended fallout from good decisions Questions to Ponder During the Episode What's the most surprising “side effect” you've experienced after making a smart money move? Have you ever optimized your budget or investment plan…only to regret it? Which metric do you track most closely in your financial life—and is it actually the right one? FULL SHOW NOTES: https://stackingbenjamins.com/unintended-credit-score-consequences-1732 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

What happens when you hand the mic to Stackers? You get a mailbag episode loaded with real-life money challenges, surprising lessons, and a few “wait, what?” moments. Joe Saul-Sehy, OG, special guest Anna Allem (a CFP® with her own winding journey into the profession), and Neighbor Doug dig into your most pressing financial questions—no fluff, no jargon, and definitely no shortage of basement-style tangents. This week's listener lineup serves up a buffet of topics: how to turn an HSA into a stealth retirement account, whether a Roth conversion is the right move (and when), the tricky little details that make or break a trust, and what's happening in the ever-shifting world of auto insurance. Along the way, we get into the mental game of money—why positive thinking might be more than motivational fluff—and how planning isn't just about the plan on paper. From Anna's seasoned perspective to OG's no-nonsense approach and Joe's knack for cutting through the noise, you'll walk away with strategies you can actually use. Plus, we can't resist a detour into AI at the Wendy's drive-thru (yes, it's a thing), proving once again that money talk is always better when you leave room for curiosity. What You'll Learn This Episode: How to decide if a Roth conversion makes sense for your tax picture Ways to supercharge an HSA for long-term wealth (and not just medical expenses) Trust basics you might be overlooking—and why that could cost you. The latest trends in auto insurance and how they might affect your rates Why mindset matters just as much as math in building financial confidence Questions to Ponder (or Argue Over in the Basement) If you were starting an HSA today, how would you use it—medical safety net or stealth retirement account? Have you considered a Roth conversion? What's the one factor holding you back? When it comes to trusts, do you prefer to keep heirs in the loop or keep plans private until needed? How do you decide when to update your insurance coverage versus just shopping for a better rate? FULL SHOW NOTES: https://stackingbenjamins.com/questions-from-the-stacker-community-1730 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

Labor Day might be about rest, but in the basement, we're getting to work on busting some of the most persistent myths in personal finance. Joe Saul-Sehy and OG welcome insurance pro Tony Steuer to unpack the shiny marketing around infinite banking and velocity banking. Spoiler: sometimes “be your own bank” really means “make your insurer rich.” From permanent life insurance pitfalls to the real math behind these strategies, Tony helps separate clever sales pitches from solid financial planning. Then we shift gears to a conversation every parent, grandparent, and future gift-giver will love. Renowned financial journalist Chuck Jaffe joins the crew, fresh from becoming a grandfather, to share how he's setting his new grandchild up for a strong financial future. Think stock portfolios for toddlers, early Roth IRA strategies, and simple systems that keep family generosity from getting lost in the shuffle. His practical, battle-tested tips will have you thinking differently about the best ways to give kids a head start. Whether you're looking to avoid costly detours or create generational wealth, this episode is equal parts cautionary tale and inspiration. You'll walk away ready to dodge financial traps, build smarter for the next generation, and maybe even rethink your own long-term giving plans. Why infinite and velocity banking aren't the slam-dunk solutions they're often sold as How to spot the red flags in permanent life insurance pitches Smart, tax-efficient ways to save for children and grandchildren Creative strategies for gifting assets that grow with the child The importance of balancing generosity with your own long-term goals Ideas to Ponder During Today's Episode Have you ever been pitched an “innovative” financial strategy that didn't feel quite right? What tipped you off? What's the most meaningful financial gift you've ever given—or received—as a child? If you could give one piece of financial wisdom to the next generation, what would it be? FULL SHOW NOTES: https://stackingbenjamins.com/permament-life-insurance-and-growing-your-money-1729 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

Why wait until your knees creak louder than your rocking chair to start enjoying life? In this episode, Joe Saul-Sehy, OG, Paula Pant (AffordAnything) and Neighbor Doug welcome Jillian Johnsrud—author of Retire Often—to share why sprinkling your life with mini-retirements might be the smartest, healthiest, and most joyful move you make before your “official” retirement date. Think of it as giving your future self a head start… without the Medicare paperwork. From negotiating time off without burning bridges, to building a financial plan that lets you step away without panic, Jillian offers a roadmap to hit pause on your career without pressing stop. We explore the balance between health, capability, and the freedom to explore, and how to sell the idea of a mini-retirement to your boss so they don't see it as a resignation letter in disguise. And because it's the basement, we also mix in some Labor Day trivia, a few personal experiments with unconventional choices, and just enough playful banter to keep you leaning in. If you've ever felt the grind wearing you down but can't picture walking away forever, this episode will help you reimagine your work-life timeline. Mini-retirements aren't just for the wealthy or the whimsical—they're for anyone ready to start living a retirement-worthy life now. How to pitch a mini-retirement to your boss without triggering an awkward HR meeting The financial prep work that makes time off less stressful and more satisfying Ways to test-drive retirement before the “official” date How to handle the skeptics (at work and at home) who think you're making a mistake Why health and capability should be part of your retirement timing equation Questions to Ponder While You Listen If you could take 3–6 months off tomorrow, how would you spend it? Would a series of shorter retirements feel more fulfilling than one long one at the end? What's the biggest barrier—financial or otherwise—keeping you from taking a break? Learn more about your ad choices. Visit podcastchoices.com/adchoices

If you've been running on fumes, juggling work deadlines, family obligations, and maybe even a neglected 401(k) or two, this episode is your permission slip to stop, breathe, and recalibrate. Joe Saul-Sehy, OG, and Neighbor Doug welcome Dr. Danielle McGeough—professor, transformational strategist, and champion of intentional living—into the basement for a conversation that's part burnout intervention, part life strategy workshop. Dr. McGeough shares how to spot the early signs of burnout before you hit the wall, and how to rebuild your days with personal rituals, playfulness, and values-driven planning. You'll hear real-world strategies for setting boundaries, aligning work with what truly matters to you, and bringing joy back into your calendar. And because we're in the basement, we also manage to sneak in some Labor Day trivia, a Broadway tangent, and a solid helping of SB-style banter. And for the Stackers worried about the financial side of burnout, we pivot in the second half to a practical discussion on managing multiple 401(k) plans—because a cluttered retirement portfolio can be just as stressful as a cluttered schedule. From account consolidation tips to understanding your investment options, this is a one-two punch of mental clarity and financial order. How to recognize the red flags of burnout (and stop it in its tracks) Why personal rituals and play can fuel productivity and joy How to align your schedule with your core values Strategies for balancing ambition with sustainability Practical steps for managing multiple 401(k) plans without losing track Why decluttering your finances can boost your mental clarity Thoughts to Ponder During the Episode What's one personal ritual you could add to your day that would give you energy instead of draining it? Have you ever consolidated old retirement accounts? What made you decide to do it (or not)? How do you know when you've hit your “enough” point with work and need to reset? What's one value you'd like to see reflected more clearly in your daily life? FULL SHOW NOTES: https://stackingbenjamins.com/how-to-reset-with-clarity-and-purpose-1727 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

Ever think, “If I just followed the playbook of the ultra-wealthy, I'd be set for life”? Turns out, that's exactly the kind of thinking that can lead you straight into the arms of a scammer. In this episode, Joe Saul-Sehy and OG break down the traps hidden inside the “invest like the 1%” mantra (and other similar phrases), complete with real-life cautionary tales, including a small-town Ponzi scheme that could've been ripped from a Netflix docuseries, and the spectacular belly flop of some YieldStreet real estate bets. But it's not all doom and gloom in the basement. You'll also get the scoop on a controversial proposal to let private equity sneak into your 401(k), practical tips for spotting shady pitches before they drain your wallet, and the reminder that a boring-but-solid financial plan beats a flashy scam every time. Plus, the guys field a listener question on long-term care insurance and unpack the often-overlooked basics of HSAs. Between headlines, trivia detours, and a dash of movie talk, this episode arms you with the street smarts to dodge the next “too good to be true” investment opportunity. It's a masterclass in protecting your money—without having to hide it under your mattress. The psychological tricks scammers use to lure in even savvy investors Why “invest like the 1%” can backfire for everyday Stackers How to evaluate alternative investments (and when to walk away) The risks and realities of adding private equity to retirement accounts Key questions to ask before buying long-term care insurance Why a strong, clear financial plan is your best defense against cons Questions to Ponder During Today's Show: Have you ever been tempted by an investment pitch that felt “exclusive”? Would you want private equity options inside your 401(k)? Why or why not? How do you decide whether an alternative investment is worth the risk? What's your personal “red flag” that makes you walk away from a deal? FULL SHOW NOTES: https://stackingbenjamins.com/how-to-avoid-common-rip-offs-1726 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

If you've ever wondered whether you should pass on your money now or make your heirs wait for the “big reveal” (cue the dramatic reading of your will), this is your episode. Joe Saul-Sehy, OG, and Neighbor Doug welcome Paula Pant from Afford Anything and Jesse Cramer from Personal Finance for Long-Term Investors to play a high-stakes round of “In or Out” with estate planning and charitable giving. Is anonymous giving a waste of good publicity? Should you set up a donor-advised fund or keep it simple? Is sharing your estate plan with your heirs wise—or an invitation to awkward holiday dinners? This isn't your average dry legal seminar. Between football analogies, dinosaur jokes, and the occasional jab at Ford's electric truck sales, our crew digs into the real-life choices Stackers face when deciding how—and when—to pass along their wealth. You'll hear hot takes, smart strategies, and maybe even a nudge to start that conversation you've been putting off. From the practical (avoiding probate, maximizing giving impact) to the philosophical (why give at all, and how much?), this episode blends useful tactics with the irreverent basement energy you know and love. It's part money talk, part game show, and 100% designed to get you thinking about your financial legacy. The pros and cons of giving now versus after you're gone How donor-advised funds work and whether they're worth your time Why anonymous giving might be overrated—or a hidden superpower Ways to avoid family drama by (maybe) sharing your estate plan early How to think about charitable giving as part of your overall financial plan Questions to ponder during the show: Would you rather give now and see the impact, or give later and leave a surprise? How much transparency do you think heirs deserve about your estate plans? If you give anonymously, are you missing an opportunity—or dodging a headache? What would you want your charitable legacy to look like? FULL SHOW NOTES: https://stackingbenjamins.com/estate-planning-giving-week-in-or-out-1725 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

What if there were a way to make charitable giving easier, more strategic, and—dare we say—more satisfying? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Len Penzo welcome Adam Nash, founder and CEO of Daffy, to demystify donor-advised funds. Whether you've never heard of them or you've been meaning to set one up, Adam walks us through how they work, why they might be a perfect fit for your giving goals, and how they can help you be more intentional with your generosity year-round. But that's not all—we also turn the spotlight on an often-overlooked money moment: handling a car insurance claim. From gathering evidence at the scene to negotiating with your insurance company, the team shares smart, practical steps to make sure you don't leave money (or protection) on the table. And, of course, Len dishes up his trademark personal finance storytelling straight from his new book, mixing in lessons you'll actually remember with tales you didn't see coming. If you've been thinking about giving more, protecting yourself better, or just want to walk away with some clever, real-world money moves, this episode's got you covered. Plus, you'll leave with an extra nudge to make your charitable giving—and your financial safety net—as strong as possible. What You'll Learn in This Episode: The basics of donor-advised funds and how they can supercharge your charitable giving Key differences between donor-advised funds and traditional giving methods How to prepare for and navigate a car insurance claim from start to finish Smart moves for documenting accidents and protecting yourself against disputes Why diversification in your giving can be as valuable as diversification in your investing How Len Penzo turns everyday money lessons into stories you'll want to retell Questions to Discuss with Your Fellow Stackers: Have you ever used a donor-advised fund—or would you consider one after hearing this episode? What's one lesson you've learned (the hard way or otherwise) from filing an insurance claim? Do you think giving should be a scheduled part of your financial plan, or something you do more spontaneously? FULL SHOW NOTES: https://stackingbenjamins.com/donor-advised-fund-deep-dive-1724 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

Estate planning might not sound like the most thrilling topic—but skipping it can create a real mess for the people you care about most. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug sit down with attorney Tim Semro to cut through the noise on wills, trusts, and life insurance. Whether you've been putting off writing a will or you're wondering if a trust is worth it, this conversation will give you a clearer path forward. Tim walks us through the essentials, from the differences between wills and trusts to the sneaky pitfalls that can trip up your beneficiary designations. We also tackle tricky scenarios—like probate headaches, planning across state (or even international) lines, and how to think about life insurance with living benefits. Plus, we swap stories about scams that hit a little too close to home and the simple moves you can take to protect your finances and family. This episode isn't about scaring you into action; it's about showing how estate planning and the right insurance can actually bring peace of mind. By the time you're done listening, you'll have a roadmap for protecting your family, making smarter decisions with your money, and avoiding the landmines that could derail your plan. And yes, there's still a trivia break and plenty of the usual basement flavor to keep things moving. What You'll Learn in This Episode: The key differences between wills and trusts—and when you might need each Why beneficiary designations matter more than you think How estate taxes and probate rules can complicate things (and how to prepare) What life insurance with living benefits is—and when it could make sense Red flags for spotting scams and fraud before they hit your wallet How to align your estate plan with your financial and family goals Questions to Ponder While You Listen (and maybe discuss with us in the Basement Facebook Group): Do you already have a will or trust in place? If not, what's been holding you back? Have you ever discovered an outdated beneficiary designation (or seen the chaos it caused)? What role do you think life insurance should play in your estate planning? FULL SHOW NOTES: https://stackingbenjamins.com/estate-planning-charitable-giving-week-1723 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

Some people chase “work-life balance” like it's the Holy Grail—spending time, money, and mental energy trying to keep work and personal life perfectly split down the middle. But what if that balance doesn't actually exist? Live from Joe's mom's basement (and not nearly as glamorous as it sounds), Joe Saul-Sehy, OG, Paula Pant, and Jesse Cramer pull back the curtain on whether we should be aiming for balance… or something else entirely. In this roundtable, the crew wrestles with the difference between work-life balance, alignment, and integration—and why chasing balance might actually keep you from a truly fulfilling life. You'll hear personal stories, some hard-won lessons about productivity, and a few well-placed digs at Nautica (including the questionable financial moves Joe made in his youth). And because no basement chat is complete without it, we bring you a trivia challenge you didn't know you needed. From managing notifications so they stop managing you, to building a life where work and personal priorities don't compete, this episode digs into the practical steps that help you get more out of both your career and your free time. Whether you're climbing the corporate ladder, running your own show, or plotting an early retirement, you'll walk away with tools to rethink how you spend your hours—and why. What You'll Learn in This Episode: Why “work-life balance” might be the wrong target—and what to aim for instead The difference between balance, alignment, and integration (and why it matters) Practical ways to keep work from swallowing your personal life whole How to reclaim your attention from constant notifications and distractions Mindset shifts that boost productivity and satisfaction in everyday life Lessons from real-life wins and missteps (including Joe's Nautica saga) FULL SHOW NOTES: https://stackingbenjamins.com/all-about-work-life-balance-1722 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

Ever wonder how to build a career, business, or financial plan that actually lasts — no matter what life throws at you? This week, we're bringing you lessons from someone who's done it for more than five generations. Cheryl McKissick Daniel, president and CEO of McKissick & McKissick, joins Joe and OG to share the strategies her family has used to overcome obstacles, land major deals (like the arena in Brooklyn and countless buildings on the historic register of places), and turn connections into opportunities. Whether you're growing a business, climbing the career ladder, or managing your money, you'll walk away with practical ideas to strengthen your network, protect your reputation, and keep moving forward. From the art of negotiation to turning big challenges into bigger wins, Cheryl offers insights you can use right now to build momentum. We'll explore how revisiting your financial plan regularly can help you avoid surprises, why reputation is an asset you can't afford to neglect, and how a strong team can take you further, faster. Plus, we'll take a break for our TikTok Minute to look at what happens when your vacation budget disappears in the name of “fun” spending. And in our headline segment, we'll cover important Medicare and insurance updates that could save you money and headaches later. Here's what you'll learn in this episode: How to use your reputation as a currency that opens doors and attracts opportunities Strategies for building a network that works for you (even when you're not in the room) Lessons from landing multi-million-dollar deals — and how to apply them to your own negotiations Why regularly reviewing your financial plan can save you from costly surprises Smart adjustments to Medicare and insurance that protect your money and peace of mind How to turn adversity into momentum, whether in your career or personal finances A lighthearted look at how “just a little fun” can destroy your budget faster than you think FULL SHOW NOTES: https://stackingbenjamins.com/story-about-building-america-1721 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

Is your 401(k) quietly working for you… or quietly working against you? In the first half of this episode, Joe Saul-Sehy, OG, and Neighbor Doug tackle the most common 401(k) slip-ups that even seasoned savers make—and how to turn yours into a retirement-building machine. Then, in the second half, we turn to a problem many Stackers don't see coming: going from saving to spending in retirement. Stacker Joel in Cleveland asks how to make the leap without feeling like you're sabotaging your future. Drawing on OG's real-world experience guiding clients through this tricky transition and Joe's research into the psychology of money, we share practical steps to help you spend without guilt, align your withdrawals with your values, and actually enjoy the freedom you've worked so hard for. Here's what you'll learn in this episode: The most expensive 401(k) mistakes—and how to fix them today Why employer matches are truly “free money” (and how to grab them) Smart moves for rolling over old 401(k)s and navigating vesting schedules The pros and cons of holding company stock in your retirement account Why the saving-to-spending switch can feel so uncomfortable—and how to get past it A simple mindset shift that helps retirees live more fully without blowing their plan How to turn your nest egg into a joy-producing income stream Whether you're in the middle of your career or staring down your first year of retirement, this episode will help you protect what you've built, optimize your plan, and make the most of your money—without second-guessing yourself. FULL SHOW NOTES: https://stackingbenjamins.com/common-401-k-mistakes-1720 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

Get ready for a rapid-fire roundtable packed with personal finance opinions that might challenge your own money playbook. In this episode, Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and Don McDonald (Talking Real Money) join Joe and OG to declare whether they're in or out on some of the most polarizing financial strategies. Whether you're just getting started or leveling up your financial life, this episode is full of practical wisdom, contrarian views, and a few laughs along the way. Oh—and somewhere in there, we may or may not sneak in a birthday surprise for one of our favorite Stackers.

Think negotiation is just for boardrooms and car dealerships? Think again. In this episode, we bring in Paula Pant from Afford Anything to show how negotiating—done well—can level up your finances, your relationships, and yes, even who does the dishes. Paula breaks down why many of us fear negotiation, how to overcome those internal roadblocks, and how setting clear “aspiration” and “reservation” points can lead to more confident conversations (and better outcomes). Whether you're asking for a raise or trying to avoid unloading the dishwasher for the fifth night in a row, her tactics are practical and empowering. Also in this episode: What most people miss about their workplace retirement plans, and whether adding a managed account is the edge you've been missing A viral TikTok proposal on setting your kids up for millions—can it really work, or is it just social media smoke? Doug delivers trivia and 1970s television references like only he can And we remember a cherished interview, David Gergen This episode is packed with useful strategies, real talk, and a few basement detours—including mafia negotiations, Lucille Ball's business savvy, and a heated debate over nostalgic TV shows. Whether you're trying to grow your wealth, negotiate more confidently, or just dodge financial TikTok traps, we've got something in here for you. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-improve-your-negotiating-skills-with-paula-pant-1718 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

Is your grocery bill beefier than your sandwich? This week, Joe Saul-Sehy, OG, and Neighbor Doug unpack inflation in a way that only we can—by biting into Len Penzo's Annual Sandwich Survey. Yes, prices are up, and yes, you can still eat well without triggering a credit card crisis. But it's not just meat and mustard on today's menu. We're also serving a fresh look at 401(k) “leakage”—that drip-drip-drip of hardship withdrawals that's turning your retirement plan into a leaky faucet. You'll get pro-level insight on how to patch those holes before your future income soaks the floor. And if you're paying for (or dreading paying for) college, Christine from the Stacker community, who works in higher ed, joins to offer sharp and timely advice on keeping costs in check—from completing the FAFSA to finding overlooked aid. Len Penzo's Sandwich Index Which sandwiches give you the most delicious bang for your inflation-adjusted buck? (Spoiler: bologna stages a quiet comeback.) 401(k) Trouble Brewing Hardship withdrawals are on the rise. Why it matters, how to avoid them, and what better options exist when life throws you a cash crisis. Tracking Expenses Like a Pro Joe, OG, and Doug explore the subtle ways inflation seeps into your budget—and how paying attention to where your money leaks gives you power back. Higher Ed, Lower Bills Stacker Christine breaks down must-know tips on navigating skyrocketing tuition, including a FAFSA pep talk that could save you thousands. Tuna vs. Roast Beef: The Sandwich Showdown Plus: Is the BLT still king? Can the humble tuna salad hold its ground against the mighty Big Mac? And where does salami fit into the sandwich power rankings? Trivia, Movie Talk, and Park City Tales No Stacking Benjamins episode is complete without a detour or three—from Doug's trivia trap to stories from the road and screen. Takeaway for Stackers: In high-cost times, it's the small wins—like swapping in store brands, packing a lunch, or tracking that budget leak—that give you the edge. And while it's tempting to ignore those tiny cracks in your retirement plan or daily spending, you're much better off fixing them before the flood. Want to brag about your favorite money-saving sandwich? Drop into the Basement Facebook group and share it—bonus points if it doesn't involve bologna. FULL SHOW NOTES: https://stackingbenjamins.com/len-penzo-2025-annual-sandwich-survey-1717 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

You just came into $50,000—no strings attached. Do you crush your debt? Supercharge your retirement? Blow it all on a podcasting-themed backyard grotto? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Jesse Cramer (The Best Interest) gather around the card table in Mom's basement to tackle one of the most common “someday” questions in personal finance: What do you do when a windfall lands in your lap? Whether it's an inheritance, work bonus, or prize money (maybe you finally won that game show you keep applying to), the panel explores what smart, emotionally grounded, and goal-aligned decisions look like in the face of sudden cash. Start With the Why Before you touch a dime, the crew walks through the importance of mindset, goals, and not falling into the “I deserve it” trap that has sunk many a lucky winner. Debt vs. Invest vs. Enjoy High-interest debt? Retirement accounts? Travel dreams? The panel weighs each strategy—and surprises us with their personal priorities. Behavioral Finance & Windfall Psychology Why do people tend to mismanage unexpected money? From mental accounting to lifestyle creep, learn the hidden traps and how to sidestep them. The 401(k) Match Dilemma Is it better to max out tax-advantaged accounts or build an emergency fund? The team hashes out smart order-of-operations for stacking your windfall right. Trivia Break: St. Paddy's Parade Edition Neighbor Doug makes sure you don't learn too much without a little distraction. Can you guess when the first St. Patrick's Day parade was held? How They'd Spend It Ever wonder what Joe, OG, Paula, or Jesse would do with an extra 50 grand? From practical moves to guilty pleasures, we get a peek into each of their financial brains. Don't let windfalls drift into “found money” syndrome—align with your long-term goals first. Paying off high-interest debt = guaranteed return. But balance it with your future-focused investments. Emotional awareness is just as crucial as spreadsheets when a windfall hits. Take a beat before making decisions. Give yourself permission to enjoy some of the money—just make sure it's intentional, not impulsive. Got a windfall story or dream scenario? Tell us how you'd handle an extra $50K in our Basement Facebook group. Let's see who would invest it, who would renovate the kitchen, and who would finally launch that mobile alpaca petting zoo. FULL SHOW NOTES: https://stackikngbenjamins.com/how-to-treat-a-financial-inheritance-1716 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

High school math left most of us staring blankly at the board, convinced compound interest was just a fancy way to say "confusing." But what if math could be fun, relevant, and—dare we say—life-changing? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome economist, education reformer, and documentary filmmaker Ted Dintersmith to the basement for a conversation that makes math feel less like a chore and more like a cheat code for life. Dintersmith, best known for his education advocacy and the acclaimed documentary Most Likely to Succeed, joins us fresh off the release of his latest book, Aftermath—a compelling look at how we rethink learning in a world that's evolving faster than ever. With over a decade visiting 500+ schools and a deep passion for practical math, Ted shares how skills like estimation, probability, and prediction can help you make smarter decisions—especially when it comes to your money. Why Prediction Beats Perfection Ted explains why being roughly right about your spending, investing, and life planning is more powerful than being precisely wrong. Consumer Math is the Real MVP From family budgets to grocery store run-throughs, Dintersmith makes a case for math that actually applies to your everyday decisions—and shows how parents and educators can teach it at home. A Fourth-Grade Science Test Gone Wrong An unforgettable story about how one exam nearly crushed a curious kid's confidence… and what it says about how we measure learning. The Financial Advisor Dilemma Solved Joe Saul-Sehy and OG unpack the key differences between bank advisors and independents, including fee structures, fiduciary responsibilities, and what really matters when choosing your financial guide. Lights, Camera, Reform Dintersmith shares the powerful stories behind his documentaries—including Most Likely to Succeed and the upcoming Multiple Choice—and why his new book Aftermath is a must-read for anyone who believes education should prepare us for real life. The Psychology of Math Anxiety and Money Mistakes We explore how bad math experiences lead to financial decision paralysis, and how to rebuild confidence one calculation at a time. Neighbor Doug's Trivia Takes the Stage Whether it connects to math or not, Neighbor Doug delivers his signature trivia moment with flair—and possibly a tangent or two. Math shouldn't be a barrier to better money decisions. This episode arms you with a fresh mindset for yourself, your kids, and maybe even your school board. If you're a math teacher, financial coach, or just someone who once cried over fractions, we want to hear from you. Join the conversation in our Facebook group, The Basement, and tell us: How are you making math practical—or how do you wish you'd learned it? FULL SHOW NOTES: https://stackingbenjamins.com/math-that-you-need-in-your-life-1715 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

Big changes are coming to the tax code—and that could mean big savings if you know where to look. On today's episode, Joe, OG, and Doug break down the most important updates in the 2025 tax laws and share smart, simple ways to keep more of your hard-earned cash. Whether you're a spreadsheet-loving tax nerd or someone who still asks, “Wait, do I have to file?”—this episode will help you navigate the new rules like a pro. Here's what we unpack: The 2025 Tax Overhaul: What changed, what stayed the same, and how it affects your bottom line Credits vs. Deductions: Why that $1 credit might be worth more than a $5 deduction (math, but fun) Above-the-Line Moves: Claim valuable deductions without itemizing New Wins for Givers and Drivers: Above-the-line charitable contributions AND (drumroll…) personal auto loan interest is back! Family Tax Breaks: Expanded dependent care accounts and beefed-up child credits 50 and Thriving: New 401(k) catch-up rules that can help you max out your retirement Listener Mailbag: JJ asks how to contribute more to his 401(k) after age 50—and we bring the strategies The TikTok Minute: Because money wisdom can live on the internet too Doug's Trivia & Financial Shenanigans™: Of course You'll walk away with clear, practical takeaways that could add thousands to your bottom line—without needing to read the tax code (you're welcome). FULL SHOW NOTES: https://stackingbenjamins.com/upcoming-tax-changes-1714 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