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!

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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!

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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!

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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!

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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!

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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!

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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!

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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!

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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!

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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!

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