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PODCAST

The Stacking Benjamins Show

StackingBenjamins.com | Cumulus Podcast Network

Named the Best Personal Finance Podcast by Bankrate.com and Kiplinger, The Stacking Benjamins Show features a light and friendly tone. Hosts Joe Saul-Sehy and OG aim to make financial literacy fun for all as they sit around the card table in Joe"s Mom"s half-finished basement and talk with experts about personal finance, saving, investing, and important money trends. As Fast Company once wrote, the Stacking Benjamins podcast "strikes a great balance of fun and functional." So join Joe and OG every

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All Episodes

62:33

How to Save Money Without Making Your Life Miserable...

The Stacking Benjamins Show ·

2025/12/05

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

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58:26

Morgan Housel: Why You Spend Money (And How to Do It...

The Stacking Benjamins Show ·

2025/12/03

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

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72:55

The Tax Basics You Should've Learned Years Ago (But...

The Stacking Benjamins Show ·

2025/12/01

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

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75:59

Board Games That Make You Smarter With Money (Without...

The Stacking Benjamins Show ·

2025/11/28

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,

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69:10

Black Friday Tech: What's Worth Buying (And What's...

The Stacking Benjamins Show ·

2025/11/26

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

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82:09

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

The Stacking Benjamins Show ·

2025/11/24

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

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74:50

How to Actually Use Money Apps the Right Way...

The Stacking Benjamins Show ·

2025/11/21

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

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77:54

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

The Stacking Benjamins Show ·

2025/11/19

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

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74:22

Should You Actually Use a Catastrophic Health Plan?...

The Stacking Benjamins Show ·

2025/11/17

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

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59:56

Why You Feel Broke Even When You're Doing Everything...

The Stacking Benjamins Show ·

2025/11/14

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

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83:29

Jonathan Clements: Why Simple Beats Complicated Every...

The Stacking Benjamins Show ·

2025/11/12

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,

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59:53

What a 12-Hour Walk Teaches You About Money (And...

The Stacking Benjamins Show ·

2025/11/10

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

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70:58

What Retirees Wish They'd Known 10 Years Ago (SB1758)

The Stacking Benjamins Show ·

2025/11/07

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

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69:14

Financial Literacy for Kids + Are Annuities Actually...

The Stacking Benjamins Show ·

2025/11/05

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

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59:48

What to Do When Money Gets Tight SB1756

The Stacking Benjamins Show ·

2025/11/03

Nobody plans for their finances to get tight. But here you are, staring at your bank account, wondering if you should panic now or wait until next Tuesday. Joe Saul-Sehy, OG, and Neighbor Doug are here to talk you off the ledge—and give you an actual plan for when money gets squeezed. Whether you're facing a layoff, dealing with reduced hours, bracing through a government shutdown, or just trying to make your paycheck last until payday, this episode is your financial storm shelter. The good news

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60:50

Tales of Financial Horror (and how we exorcised them)...

The Stacking Benjamins Show ·

2025/10/31

Pop quiz: What's scarier than a haunted house? Opening your credit card statement after a "just this once" shopping spree turned into a six-month spiral.Joe Saul-Sehy and Neighbor Doug gather 'round the basement campfire with Doc G (Jordan Grumet from Earn and Invest), Jesse Cramer (Personal Finance for Long Term Investors), and special guest Emily Egashira—AKA Your Friend Em from TikTok and Instagram fame—to share the financial horror stories that still wake them up at night. We're talking

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69:33

Banishing Money Monsters: How to Talk Money With...

The Stacking Benjamins Show ·

2025/10/29

You know what's truly terrifying? Realizing you and someone you share money decisions with have completely different ideas about finances—and you're both convinced you're right. Joe Saul-Sehy and OG welcome Doug and Heather Bonaparte, a CFP and business partner duo who've mastered the art of not killing each other over finances. And when you work together AND live together? Let's just say they've had plenty of practice navigating the financial frights that haunt any relationship where money's

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63:36

Real Money Horror Stories (And How Not to Star in...

The Stacking Benjamins Show ·

2025/10/27

What's scarier than a haunted house? Looking at your retirement account after ignoring it for five years.Joe Saul-Sehy, OG, and Doug welcome back Chuck Jaffe (Money Life with Chuck Jaffe) for his legendary annual Halloween visit—and this year, he's bringing two treats to the basement. First up: Chuck's Halloween Money Game for kids. Picture this: trick-or-treaters can take one piece of candy and walk away... or they can play a game where they might win more candy, actual money, or lose it all

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66:11

You've Got Enough Money to Quit. Should You? SB1752

The Stacking Benjamins Show ·

2025/10/24

Here's a question nobody in the FIRE movement talks about: What if you reach financial independence... and don't want to quit? Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Doc G (Earn & Invest) tackle the idea of Reverse FIRE—people who've hit their number but choose to keep working anyway. And before you roll your eyes, hear them out. Because it turns out that having enough money doesn't automatically make you happy. And for a lot of people, walking away from work means walking away from

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73:35

Your Money Problems Aren't Math Problems (They're...

The Stacking Benjamins Show ·

2025/10/22

Here's the secret nobody tells you: your money problems probably aren't math problems.Joe Saul-Sehy and OG sit down with Carl Richards—financial planner, New York Times columnist, and the guy behind those brilliant "Sketch Guy" drawings that make money actually make sense. Carl's spent his career helping people untangle their relationship with money, and his big insight? Most of us are overthinking it. Your financial plan shouldn't feel like a calculus final. It should feel like a map you can

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1,401 results

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