The Stacking Benjamins Show
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 Monday, Wednesday and Friday as they read your letters, discuss major headlines, and throw in some trivia and laughs for free.
Episodes
November 7, 2025 • 70 mins
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 s...
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November 5, 2025 • 69 mins
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...
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November 3, 2025 • 59 mins
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 ...
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October 31, 2025 • 60 mins
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 ...
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October 29, 2025 • 69 mins
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 ...
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October 27, 2025 • 63 mins
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 g...
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October 24, 2025 • 66 mins
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...
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October 22, 2025 • 73 mins
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 should...
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October 20, 2025 • 70 mins
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 your kids a smart move or an expensive mistake? How much life insurance do you actu...
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October 17, 2025 • 67 mins
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: how you create the conditions for opportunity to find you in the first place.
This e...
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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 timeless lessons he learned from decades steering one of the world’s most innovative comp...
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October 13, 2025 • 70 mins
When gold shines, so do the hot takes, and today, the Stacking Benjamins crew dives into what this record-breaking surge really means for your money. Joe Saul-Sehy, OG, and Neighbor Doug kick off the week with their signature Monday salute to our troops before digging into the glittering headlines: gold prices are hitting new highs… but does that make it a smart investment or just financial fool’s gold?
From breaking down why gold...
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October 10, 2025 • 73 mins
Who says you have to wait until 65 to clock out and start living your best life? On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, Paula Pant (Afford Anything), OG, and special guest Sean Mullaney—author, CPA, and early retirement strategist—explore how to design a life that lets you walk away from the office sooner and happier.
From tax-smart withdrawal strategies to dialing in your lifestyle design, this conversatio...
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October 8, 2025 • 61 mins
What if building wealth wasn’t just about stacking dollars — but also stacking good deeds? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG sit down with Mel Dorman, a powerhouse real estate investor who turned humble beginnings (yes, dumpster diving beginnings) into a thriving portfolio of 34 rental units in just five years. And she didn’t just build wealth — she built community along the way.
From negotiating...
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October 6, 2025 • 60 mins
What if the key to a richer life isn’t about chasing the next hot stock or grinding harder — but learning to master the timeless truths of money? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug pay tribute to legendary financial writer Jonathan Clements by revisiting five of his most impactful lessons. These aren’t complicated formulas or secret hacks — they’re the kind of deceptively simple ide...
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October 3, 2025 • 59 mins
If your financial plan feels more like a vague wishlist than a real roadmap, this episode is about to change that. Live from the basement of YouTube HQ, Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long-Term Investors) roll up their sleeves and dig into the three most common — and costly — mistakes people make with their money plans. Whether you’re just starting out or you’ve been stacking...
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October 1, 2025 • 68 mins
Think your retirement plan is bulletproof? Think again. In this eye-opening episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by certified financial planner Jeremy Keil, CFP® to walk you through the steps to building a retirement plan that won’t crack under pressure. From mapping out your spending before you ever leave the workforce to crafting a tax strategy that keeps more money in your pocke...
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September 29, 2025 • 64 mins
Think the American Dream is slipping out of reach? Think again. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug tackle one of the biggest financial questions of our time: how much does it really cost to live the life you want — and is it still possible? Spoiler alert: it is, but it takes more than a paycheck and a Pinterest board. We break down fresh research from Investopedia, the rising price ...
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September 26, 2025 • 74 mins
What if tweaking just a few “knobs” in your 401(k) could mean the difference between retiring with confidence or wondering if you’ll ever stop working? In this spirited episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by three of our favorite money minds — Paula Pant from AffordAnything, Jesse Cramer from Personal Finance For Long Term Investors, and Lacey Langford from The MILMO Show — to bre...
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September 24, 2025 • 79 mins
What if the secret to enjoying your job isn’t grinding harder but stepping back and rethinking how work fits into life? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome special guest Shemin Nurmohamed to unpack the Paris Paradox: balancing work and leisure without sacrificing ambition. From cultural perspectives on downtime to the productivity perks of unplugging, Shemin shows why working...
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