The Stacking Benjamins Show

The Stacking Benjamins Show

Named 2023 Best Personal Finance podcast by Bankrate.com, The Stacking Benjamins Show has 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

April 25, 2025 66 mins
What do zipper injuries, holiday party mishaps, and servant leadership have in common? They’re all part of today’s wide-ranging look at careers—what to do, what not to do, and how to make your next move smarter (and safer). Joe Saul-Sehy, OG, and Neighbor Doug are joined by contributors Sandy Smith, Jesse Cramer, and a few classic career stories from the SB vault. Together, they explore: The surprising power of likability in the...
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How do you stand out in a competitive workplace—without shouting or burning out? In this episode, Joe and OG sit down with Lorraine K. Lee, a sought-after keynote speaker and former LinkedIn and Prezi leader, to dig into the real strategies behind building a career brand that lasts. Lorraine shares what she’s learned from coaching thousands of professionals, plus her own journey from behind-the-scenes to center stage. She introduc...
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Today’s episode blends career strategy with financial know-how, because who says you can’t build your personal brand and your balance sheet at the same time? Joe Saul-Sehy and OG explore what it really means to shape your professional reputation—from the way you show up in meetings to how you set (and measure) your career goals. Whether you're climbing the ladder, shifting industries, or mentoring others, this episode delivers prac...
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Some people master reinvention. They move from one stage of life to the next with confidence, purpose, and an eye on long-term success. What if your financial plan could do the same? In today’s roundtable, Joe is joined by Alyssa Maes, Roger Whitney (The Retirement Answer Man), and OG to talk about what it takes to build wealth that lasts—not just through one season of life, but through all of them. 🎯 Inside the episode: What s...
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What Taylor Swift teaches us about strategy, long-term thinking, and building an empire. Taylor Swift isn’t just a pop icon—she’s a master strategist. And in this episode, we unpack exactly how she built a cultural and financial empire with smart moves that offer powerful lessons for any Stacker. Joe Saul-Sehy sits down with Kevin Evers of Harvard Business Review Press to explore: How Taylor’s early partnerships set her on a path...
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It’s Taylor Swift week in the basement, and we’re kicking things off by looking at the business behind the beats. Joe, OG, and the gang pull back the curtain on the intentional, savvy moves that took Taylor from breakout teen artist to industry powerhouse—and why her playbook might just work for your financial life, too. We’re talking about more than album drops. This episode covers: The power of controlling your own creative ou...
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Feeling anxious about where your money’s going? You’re not alone—and you’re not without a plan. In today’s episode, Joe is joined by OG, Mom’s neighbor Doug, and two sharp minds from the personal finance world: Paula Pant from Afford Anything and Dr. Jordan Grumet from Earn and Invest. Together, they take a deep dive into the many faces of investment risk, from the obvious to the overlooked. Because when it comes to your financial ...
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Market volatility, overthinking portfolios, and why simple might be smarter. Trade wars. Tariffs. Tumbling markets. When headlines scream and your portfolio wobbles, what’s a Stacker to do? Today, we tackle how to invest confidently during uncertain times—without overcomplicating your strategy or losing sleep. We start by breaking down smart ways to manage volatility, whether you’re just getting started or already a seasoned inves...
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Tariffs got you sweating? We’ve got the strategy (and the LaCroix) to help you chill. Markets are wobbling, headlines are screaming, and you’re wondering if your portfolio is about to implode. Take a deep breath—and head down to the basement. In this episode, Joe Saul-Sehy, OG, and Mom’s neighbor Doug tackle the turbulence triggered by recent tariff changes. While others panic, we’re pouring the coffee and walking you through how...
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Entrepreneurship, financial anxiety, and a guinea pig (yes, really). When you’ve got a stuffed guinea pig on your desk and a mic in front of you, it’s only a matter of time before you talk about that one time you ate guinea pig in Peru. (Spoiler: It was pretty good.) That’s how we open today’s show—but from there, things get real. Today’s main event features Rudy Mawer, founder of 60 Day Hustle, who joins Joe Saul-Sehy to share hi...
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Is good debt a myth? Should we all chase FIRE? The basement panel weighs in. In today’s Financial Concepts Friday roundtable, Joe brings the basement crew together for a lively “In or Out” debate on some of the most polarizing personal finance topics out there. Are we in or out on the idea of “good debt”? Do budgets really matter when you’re just starting out? Should you talk about money with your friends and family… or is that st...
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Ever been told to buy the biggest house you can afford... to “motivate yourself”? Or to skip insurance because “nothing bad will happen”? Yeah—us too. And we’ve got some thoughts. In this episode, Joe, OG, and Doug break down the Top 5 Worst Financial Tips they’ve ever heard—and more importantly, why taking them seriously could leave your finances in a flaming dumpster behind your dreams. From personal debt confessions to debates...
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Is financial literacy missing from your life like that sock you swear went in the dryer? Tiffany Aliche, AKA The Budgetnista, is here to help you find it—minus the lint. She shares her journey to financial wholeness and takes us behind the scenes of her brand-new PBS special. Meanwhile, Joe and OG break down why financial education starts with community (not overpriced guru courses), why ‘Buy Now, Pay Later’ is the financial equiva...
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Ever fallen for an investment that seemed like a sure thing... until it wasn’t? You’re not alone. Today, we shine a light on some of the worst investment advice out there—and help you steer clear of it. Joining Joe at the roundtable are: Paula Pant from Afford Anything Jesse Cramer from Personal Finance for Long-Term Investors And Don McDonald, financial pro and former astronaut (not really, but just go with it) from Talkin...
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Ever wondered how the top financial minds avoid disaster while the rest of us are busy panic-Googling “best investments 2024”? Today, Joe welcomes Barry Ritholtz of Ritholtz Wealth Management down to Mom’s basement for a conversation that flips typical investment advice on its head. It’s not about what to do—it’s about what not to do if you want to grow your money without losing your sanity. Barry shares battle-tested insights from...
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What do weddings, wineries, and Whoppers have to do with smart investing? This week, Joe, OG, and Doug kick off the episode with stories from the road—including a surprise credit card confession that somehow involves a Burger King (because of course it does). But then the gang shifts gears and dives into real money talk, breaking down investing wisdom from the legendary Barry Ritholtz. From navigating market cycles to keeping your...
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Ever wonder why some people crush their financial goals while others keep hitting snooze? Today, we’re talking about the secret sauce behind sticking to a financial plan—and no, it’s not just “wanting it more” (though that helps). Joining Joe in the basement is OG, alongside personal finance expert Jesse Kramer from The Best Interest and CFP Dana Anspach from Sensible Money. Together, they’ll break down why staying financially moti...
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Ever feel like you're stuck in a rut, spinning your wheels, or just running low on motivation? Today, we crack the code on sustaining drive and avoiding complacency with former sports agent Molly Fletcher, who’s worked with some of the biggest names in sports and has been dubbed the female Jerry Maguire. She breaks down the fine line between contentment and coasting, plus shares keys to staying at the top of your game—from managing...
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Ever start a new financial goal feeling unstoppable, only to lose momentum when life gets in the way? Staying motivated isn’t just about working harder—it’s about working smarter. Today, Joe and OG take a deep dive into Dynamic Drive, the key to keeping your financial momentum going without burnout. We’ll break down the seven essential pillars—mindset, energy, discipline, curiosity, resilience, connection, and confidence—so you’re...
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March 14, 2025 57 mins
Ever feel guilty about that $7 airport coffee or the mystery fees that somehow turn your $15 DoorDash order into a $40 financial regret? You’re not alone. This episode, Joe Saul-Sehy is joined by Paula Pant (Afford Anything) and Justin Peters (The Struggle Is Real) to unravel the sneaky ways convenience drains our wallets. In this episode: Airport Food: The Ultimate Financial Heist – Why does a sad turkey sandwich cost more than...
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