The Stacking Benjamins Show

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!

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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/

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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/

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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!

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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

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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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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.