The Stacking Benjamins Show

• 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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• The Smart Person's Guide to Black Friday Deals (SB1765)

  Black Friday is coming, and you've got two choices: get trampled at 3 a.m. for a discount air fryer, or learn how the pros actually save hundreds without the drama. Joe Saul-Sehy and Neighbor Doug kick off Black Friday week with the perfect blend of strategy and sanity. First up: Australian comedian Josh Liston tries to make sense of American Thanksgiving traditions and why we consider waking up before dawn to fight strangers over discounted electronics "normal holiday fun." Spoiler: he's not buying it. Then Regina Conway from Slick Deals drops in with the actual playbook. Regina breaks down when to shop during Black Friday week (different categories peak on different days), how to stack coupons with cashback and gift card deals for maximum savings, and why subscriptions and memberships might be the smartest budget-friendly gifts you're not considering. She also reveals how the Slick Deals community spots hidden bargains before they disappear—and how you can do the same. But here's where it gets real: Joe, Doug, and Josh tackle Buy Now Pay Later schemes like Affirm and Klarna. They're everywhere this season, and they're tempting. They're also the financial equivalent of eating Halloween candy for breakfast—feels great in the moment, regrettable by lunch. You'll learn exactly when these services make sense (rare) and when they're just a trap disguised as convenience. Whether you're hunting deals or trying to avoid holiday debt, this episode is your survival guide for coming out ahead. What You'll Walk Away With: • Regina Conway's insider strategy for when to shop during Black Friday week (hint: timing matters more than you think) • How to stack coupons, cashback offers, and gift card deals to maximize every purchase • Why subscriptions and memberships make surprisingly smart (and budget-friendly) holiday gifts • Grocery hacks that actually save money during the most expensive shopping weeks of the year • The truth about Buy Now Pay Later—when it's useful and when it's just expensive debt with good marketing • How community-powered deal sites like Slick Deals help you find and vet bargains before they vanish • Smart strategies to enjoy the holidays without the January credit card hangover This Episode Is For You If: • You want Black Friday deals without the 3 a.m. wake-up call or the crowds • You're trying to save money this season but feel overwhelmed by all the "deals" • You've been tempted by Buy Now Pay Later but aren't sure if it's smart or stupid • You want to give great gifts without blowing your budget (or your sanity) • You believe there's a smarter way to shop than fighting strangers for discounted TVs What's Your Black Friday Strategy? Are you a doorbuster warrior, an online deal hunter, or someone who avoids the whole thing? Drop your approach in the comments—and if you've got a Black Friday horror story (or victory), the basement wants to hear it. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-save-big-this-black-friday-regina-conway-1765 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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• How to Actually Use Money Apps the Right Way (According to FinTech Pros) SB1764

  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

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