The Stacking Benjamins Show

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

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

How to Actually Listen (Not Just Wait to Talk) SB1763

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

Should You Actually Use a Catastrophic Health Plan? (& more questions from YOU!) SB1762

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

Why You Feel Broke Even When You're Doing Everything Right (SB1761)

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