The Stacking Benjamins Show

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 wo...

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 b...

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...

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...

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 th...

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 McFar...

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 found...

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...

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...

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'...

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...

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 Inst...

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...

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...

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 does...

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 overthinki...

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? Ho...

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 fin...

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...

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...

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...

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 com...

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’r...

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 s...

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 strate...