The Stacking Benjamins Show

• How to Save Money Without Making Your Life Miserable (SB1770)

  Here's the problem with most frugality advice: it makes you feel like a monk who's taken a vow of joylessness. Joe Saul-Sehy and Neighbor Doug gather the roundtable crew—Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and Andy Hill (Marriage, Kids, and Money)—to prove that frugality isn't about deprivation. It's about designing a life that feels good and costs less. The conversation gets real fast: what's the difference between thoughtful frugality and soul-crushing penny-pinching? How do you cut spending without cutting joy? And why do some people thrive on frugal challenges while others just end up resentful and burnt out? The crew shares their own tactics, from "shopping your fridge" (a shockingly high-ROI habit most people ignore) to the power of frugal sprints instead of permanent deprivation mode. They break down how to align your spending with your actual values instead of society's expectations, why raising income often beats shaving another $3 off your grocery bill, and how to turn frugality into something your kids actually want to participate in (no guilt trips required). You'll also hear about the expenses each of them refuses to cut no matter how frugal they get, because smart money management isn't about eliminating everything; it's about keeping what matters and ditching what doesn't. Plus: stories about mystery freezer leftovers, subscription fees that sneak in like cat burglars, and Doug's perspective on... well, whatever Doug decides matters that day. What You'll Walk Away With: • The difference between frugality that improves your life and penny-pinching that just makes you miserable • Why "shopping your fridge" might be the highest-return grocery habit you'll ever adopt • How to design spending around your actual values instead of just cutting blindly • The power of "frugal sprints"—short-term challenges that work without long-term burnout • How to involve your kids in frugal habits without making them feel deprived • Why focusing on raising income often matters more than obsessing over tiny budget cuts • Which expenses the pros refuse to cut—and why knowing your "worth it" list matters This Episode Is For You If: • You want to save money but refuse to live like you're broke when you're not • Traditional frugality advice makes you feel guilty about things that actually bring you joy • You're trying to cut spending but can't figure out where to start without feeling deprived • You want to model smart money habits for your kids without making them fear spending • You're tired of finance advice that assumes everyone should want the same lifestyle Before You Hit Play, Think About This: What's the one expense you refuse to cut, no matter how frugal you get? And what does that tell you about what actually matters to you? Drop your answer in the comments—we want to know what's on everyone's "worth it" list. FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-save-money-without-making-your-life-miserable-sb1770/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Morgan Housel: Why You Spend Money (And How to Do It Better) SB1769

  Here's something nobody tells you: knowing how to make money is easy compared to knowing how to spend it well. Morgan Housel, bestselling author and one of the sharpest minds in personal finance, is back in the basement with Joe Saul-Sehy, OG, and Neighbor Doug to tackle the question most financial advice completely ignores: why do we spend the way we do, and how can we get better at it? This isn't about budgeting apps or cutting lattes. It's about understanding the psychology underneath every swipe of your card. Morgan shares stories from his early days working valet for the ultra-wealthy—the spending patterns he observed, the misery he witnessed, and the lessons that changed how he thinks about money forever. Turns out, having more money doesn't automatically make you better at spending it. In fact, it often makes you worse. The conversation digs into what actually creates happiness (spoiler: it's not more stuff), why contentment matters more than your net worth, and how true financial independence isn't about the size of your portfolio—it's about the freedom to make choices that align with your actual values. Morgan also breaks down what Warren Buffett's retirement announcement reveals about staying grounded while building wealth, and why comedians might understand money better than most economists. Plus: Doug takes a trivia detour to a surprisingly risqué national park (because of course), and the crew wraps with binge-worthy recommendations for your next couch night. If you're tired of chasing more and ready to figure out what enough actually looks like, this episode is required listening. What You'll Walk Away With: • Why spending money well is a psychological skill, not a math problem—and how to develop it • What Morgan learned about wealth and misery from parking cars for millionaires in their driveways • The hidden drivers behind your financial decisions (and how to spot them before they derail you) • Why contentment—not consumption—is the real key to long-term happiness • What true financial independence actually means (hint: it's not a number in your bank account) • How Warren Buffett's approach to retirement reveals timeless principles about money and legacy • Simple guiding principles to help you spend smarter and live calmer This Episode Is For You If: • You've hit financial goals but still don't feel satisfied • You're tired of spending money on things that don't actually make you happier • You want to understand why you make the money decisions you do (even the questionable ones) • You're curious what actually separates people who enjoy their money from people who just have it • You believe there's more to financial success than just accumulating more Before You Hit Play, Think About This: What's one purchase you made that brought way more joy than its price tag would suggest—and can you figure out why? That's the kind of spending Morgan's talking about. Drop your answer in the comments—the basement wants to hear what actually brought you happiness. FULL SHOW NOTES: https://www.stackingbenjamins.com/the-art-of-spending-money-with-morgan-housel-1769/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• The Tax Basics You Should've Learned Years Ago (But Nobody Taught You) SB1768

  Let's be honest: taxes feel like that thing you're supposed to understand but somehow never learned, and now you're too embarrassed to ask. Joe Saul-Sehy, OG, and Neighbor Doug welcome Hannah Cole—artist-turned-tax-pro and author of the brand-new book Taxes for Humans—to finally explain taxes in language that doesn't require a CPA license to understand. Hannah's built her career translating tax code for freelancers, side hustlers, and small business owners who just want to know what they can deduct, what'll get them audited, and how to stop drowning in shoebox receipts. She breaks down the real difference between a legitimate business expense and wishful thinking, how to track startup costs without losing your mind, and why the bookkeeping system that works is the one you'll actually use (spoiler: it doesn't have to be fancy). Whether you're launching a side gig, running a creative business, or just trying to keep the IRS from ruining your holiday season, Hannah's got the roadmap. Then Joe and OG shift gears to tackle the "AI bubble" conversation everyone's having—is this tech hype justified, or are we watching 1999 all over again? They break down how to think about market froth without panicking, why smart investors don't build their strategy around TikTok prophets predicting doom, and how to prepare your portfolio for volatility without making fear-based moves. Plus: Doug delivers trivia about Richard Pryor's Blazing Saddles days, because even tax talk deserves a palate cleanser. What You'll Walk Away With: • Tax basics explained in actual human language (finally)—what counts as a deduction and what's just wishful thinking • How to set up simple, sustainable bookkeeping systems for side gigs or small businesses that you'll actually maintain • The smartest way to track startup expenses without drowning in receipts or spreadsheets • Why the IRS isn't as scary as you think when you've got your basics covered • How to think about AI market hype without getting swept up in either the euphoria or the panic • Smart strategies for preparing your portfolio for volatility without making emotion-driven decisions • Why the right tax and investing systems buy you back time, creativity, and peace of mind This Episode Is For You If: • You've been winging it on taxes and know you're probably missing deductions (or making mistakes) • You run a side hustle but have no idea what you can actually write off • Tax season makes you anxious because you're never sure if you're doing it right • You're hearing AI bubble talk everywhere and wondering if you should be worried about your investments • You want systems that are simple enough to actually follow, not perfect enough to abandon by February Before You Hit Play, Think About This: What's the tax mistake you wish you could warn your younger self about? Drop it in the comments—we're all learning here, and sometimes the best lessons come from what we got wrong the first time. FULL SHOW NOTES: https://www.stackingbenjamins.com/tax-basics-for-side-hustlers-ai-market-tips/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Board Games That Make You Smarter With Money (Without Feeling Like School) SB1767

  Here's a secret: some of the best financial education doesn't come from books or podcasts. It comes from a board game box. Joe Saul-Sehy welcomes Kylie Prymus, board game expert and owner of Pittsburgh's award-winning store Games Unlimited, for a conversation about the games that sneak money lessons into brilliant gameplay. These aren't boring "educational games" that make kids groan—they're genuinely fun strategy games that happen to teach supply and demand, resource management, risk assessment, and long-term planning better than most finance courses. Kylie walks through his top picks for economic games that'll make you (and your kids, and yes, your brother-in-law) think differently about money. From deck-builders like Dominion that teach portfolio diversification to Food Chain Magnate (basically an MBA in a box, but way more entertaining), these games turn financial concepts into actual decisions with consequences you can see play out in real time. But this isn't just about learning—it's about leveling up your holiday gatherings. Kylie shares his favorite cozy games for the season, from the absurdly cute cat-themed strategy game Boop to party games like Monikers that even Uncle Larry can't ruin. Whether you need something cooperative to bring the family together or competitive enough to settle old scores, this episode has you covered. Plus: you'll hear why game stores like Games Unlimited curate experiences (not just inventory), and how the right game can turn a tense holiday gathering into something people actually want to repeat. What You'll Walk Away With: • The board games that teach money concepts like budgeting, income streams, and resource management without feeling like homework • Why Dominion, Food Chain Magnate, and other economic games are secretly brilliant financial teachers • Kylie's top holiday game picks—from cozy strategy games to party games that work for any crowd • How game mechanics like deck-building and resource trading translate directly to real-world money decisions • What to look for when choosing games that work for both newbies and strategy enthusiasts • Why games teach financial lessons better than lectures—and how to use that with kids (or adults who need a refresh) • The surprising ways marketing, scarcity, and community building show up in tabletop games This Episode Is For You If: • You want to teach your kids about money in a way that doesn't feel like a lecture • You're looking for games that are actually fun but happen to build financial thinking • Your family game nights need an upgrade beyond Monopoly arguments • You're curious about board games but don't know where to start • You believe the best learning happens when you're having too much fun to notice you're learning What's Your Money Game? Drop your answer in the comments: What board game taught you a real money lesson, even if it wasn't trying to? Or if your financial personality were a board game, which one would it be? The basement wants to know—and we're always looking for new game recommendations. FULL SHOW NOTES: https://www.stackingbenjamins.com/kylie-prymus-board-games/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Black Friday Tech: What's Worth Buying (And What's Just Hype) SB1766

  Black Friday's coming, your inbox is screaming deals at you, and you're trying to figure out: is this tech actually worth it, or will it be collecting dust by Valentine's Day? Joe Saul-Sehy, guest co-host CFP Anna Allem, and Neighbor Doug bring in Bridget Carey from CNET to cut through the holiday tech chaos. Bridget's spent her career testing gadgets, and she's here to tell you what's actually worth your money this season—from Nintendo's surprisingly strong lineup to handheld gaming devices like Steam Deck and Xbox Cloud that might replace your console. She also warns you away from AI-powered appliances that still feel like they're arguing with you instead of helping. Bridget breaks down the smart way to approach Black Friday and Cyber Monday without wrecking your December budget, which deals are real and which are manufactured hype, and why some tech gifts send a very specific message to your in-laws (and maybe not the one you want). Then the conversation shifts from tech temptations to investing platforms—specifically Robinhood. The confetti animations are fun, the interface is slick, but is it actually built for serious long-term investing? Joe and Anna dig into where Robinhood works, where it distracts, and why your retirement plan might need something more substantial than gamified stock trading and crypto side quests. Plus: Doug delivers Thanksgiving-adjacent trivia, and the crew takes a nostalgic detour through Skip-Its and Long Furbys that'll fuel your next holiday gathering conversation. What You'll Walk Away With: • Bridget Carey's insider guide to which holiday tech deals are legit and which are overhyped garbage • The best gaming and gadget gifts this season (from someone who actually tests this stuff for a living) • Why some AI appliances still feel like expensive beta tests you're paying to debug • Smart strategies for Black Friday and Cyber Monday that don't demolish your December budget • The honest truth about Robinhood: where it shines and where serious investors should look elsewhere • How investing platforms subtly influence your behavior—and whether that's helping or hurting you • How to stay grounded when shiny objects (tech or financial) start calling your name This Episode Is For You If: • You're staring at Black Friday ads wondering which deals are actually worth it • You want tech gift advice from someone who isn't trying to sell you something • You've been using Robinhood and wonder if it's actually helping your long-term investing goals • You're curious whether the flashy features on investing apps are making you a better or worse investor • You need a reality check before holiday spending turns into January regret Before You Hit Play, Ask Yourself: What's the worst tech purchase you've ever made? Bonus points if it broke before New Year's. Drop it in the comments—misery loves company, and we're building the ultimate "do not buy" list together. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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