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 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

1396

1H 20min

How to Actually Use Money Apps the Right Way (According to FinTech Pros) SB1764What 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

1395

1H 14min

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