Best StackingBenjamins.com | Cumulus Podcast Network Podcasts (2025)

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How to Actually Use Money Apps the Right Way (According to FinTech Pros) SB1764 1:14:50

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3d ago1:14:50

1:14:50

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)—fo…

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How to Actually Listen (Not Just Wait to Talk) SB1763 1:17:54

5d ago1:17:54

1:17:54

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 conver…

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Should You Actually Use a Catastrophic Health Plan? (& more questions from YOU!) SB1762 1:14:22

7d ago1:14:22

1:14:22

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 …

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Why You Feel Broke Even When You're Doing Everything Right (SB1761) 59:56

10d ago59:56

59:56

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 Millenn…

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Jonathan Clements: Why Simple Beats Complicated Every Time (SB1760) 1:23:29

12d ago1:23:29

1:23:29

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 S…

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What a 12-Hour Walk Teaches You About Money (And Life) SB1759 59:53

14d ago59:53

59:53

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 …

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What Retirees Wish They'd Known 10 Years Ago (SB1758) 1:10:58

17d ago1:10:58

1:10:58

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 a…

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Financial Literacy for Kids + Are Annuities Actually Safe? SB1757 1:09:14

19d ago1:09:14

1:09:14

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 …

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What to Do When Money Gets Tight SB1756 59:48

21d ago59:48

59:48

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, brac…

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Tales of Financial Horror (and how we exorcised them) SB1755 1:00:50

24d ago1:00:50

1:00:50

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 Emil…

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Banishing Money Monsters: How to Talk Money With Anyone (Partners, Roommates, or Coworkers) SB1754 1:09:33

26d ago1:09:33

1:09:33

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 t…

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Real Money Horror Stories (And How Not to Star in Your Own) SB1753 1:03:36

28d ago1:03:36

1:03:36

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: …

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You've Got Enough Money to Quit. Should You? SB1752 1:06:11

1M ago1:06:11

1:06:11

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. Beca…

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Your Money Problems Aren't Math Problems (They're People Problems) SB1751 1:13:35

1M ago1:13:35

1:13:35

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 mon…

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Should You Drain Your Emergency Fund? (And 4 Other Money Questions Keeping You Up) SB1750 1:10:43

1M ago1:10:43

1:10:43

You've got questions. We've got two CFPs and a former planner ready to hash it out. Joe Saul-Sehy, OG, Doug, and CFP Anna Allem tackle the money decisions you're actually losing sleep over—and here's the thing: they don't always agree on the answer. That's the point. Should you drain your emergency fund to pay off debt? Is whole life insurance for …

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What Lucky People Do Differently With Money (SB1749) 1:07:29

1M ago1:07:29

1:07:29

Think some people just have all the luck? Think again. Joe, OG, Paula Pant (Afford Anything), and Chris Luger (Heavy Metal Money) break down what separates people who catch breaks from those who don't...and spoiler alert: it's not about being in the right place at the right time. It's about what you DO when opportunity shows up. And before that: ho…

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How to Deliver the “WOW” in Everyday Life (with longtime former Royal Caribbean Chairman and CEO Richard Fain) SB1748 1:11:56

1M ago1:11:56

1:11:56

You don’t have to command a cruise ship (or a boardroom) to lead with purpose. On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome Richard Fain, longtime chairman and former CEO of Royal Caribbean Group, for a conversation that’s not about corporate leadership… but about life leadership. Richard shares timel…