The Stacking Benjamins Show

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 c...

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 ,...

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...

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 pe...

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,...

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...

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...

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 naviga...

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 bre...

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 stayin...

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, resilienc...

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 sa...

Choosing the Best Tax Software for Your Needs Tax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you're a side hustler, crypto investor, or just looking for a free filing solution. Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by whi...

Ever wondered if working for yourself could be the game-changer your finances need? Grant Sabatier thinks so, and today, he’s diving into the realities of entrepreneurship —from smart strategies to potential pitfalls. Where to start if you’re considering entrepreneurship – Not every side hustle is a winner, so how do you know if this path is right for you? The power of systems and constraints – Wh...

Feeling the pressure to constantly tweak your investments? Today, we uncover the surprising benefits of financial inaction with insights from CFP Dana Anspach , Len Penzo, and OG. We dive into the wisdom of sometimes doing nothing—because, as it turns out, sitting on your hands (financially speaking) can be a power move. Why lazy portfolio management might be the smartest strategy you’ll ever adop...

A great financial plan isn’t just about numbers—it’s about creating a roadmap that turns dreams into reality. Today, Joe and OG take a trip down memory lane, reflecting on their favorite parts of building a great financial plan. Whether you're tackling long-term goals , fine-tuning your tax strategy , or simplifying complex decisions , they’ll walk you through the key elements that turn financial...

Ever felt overwhelmed by buying a car or managing your time ? You’re not alone. Today, we tackle both topics with expert insights and a few unexpected surprises along the way. Car buying decoded – Joe sits down with Phil Reed, Senior Consumer Editor at Edmunds , to break down the best strategies for buying new or used cars, leasing vs. buying, and negotiating with dealers like a pro. The ultimate...

If disaster struck tomorrow, would your financial essentials be ready to grab and go? Today, Joe —along with contributors Paula Pant from Afford Anything , Jesse Cramer from Personal Finance for Long-Term Investors , and our resident expert OG—assemble the ultimate financial go bag. Meanwhile, Doug handles his usual duties as announcer, trivia master, and general chaos instigator. The must-have do...

Is your insurance setup rock-solid, or are you unknowingly leaving gaps that could cost you big time? Today, we break down the essentials of managing risk in our no-nonsense (but totally entertaining) insurance guide. How much coverage do you really need? We tackle the must-haves and the unnecessary add-ons that might just be draining your wallet. Auto, home, life, and disability insurance—what’s...

Ever feel like your budget is running you instead of the other way around? Today, we’re bringing in Shaun Morgan from The Teacher Money Show and Kristin Wade , budgeting coach at My Budget Coach , to help you flip the script. They’ll share how tracking your expenses is the first (and easiest) step toward financial freedom , why budgeting shouldn’t feel like punishment, and how to make your money w...

Is it time to break up with international stocks? They’ve been underperforming U.S. markets for years, so should we finally call it quits, or is there still hope for a global comeback? On today’s episode, Joe, OG, Paula Pant, and Jesse Cramer dig into the great international investing debate. Are international funds a lost cause? The panel unpacks why they’ve lagged U.S. stocks and whether diversi...

Ever experienced the gut-wrenching moment of losing a job—or worried about what you’d do if it happened? Today, we tackle how to prepare, what to do immediately, and the smartest moves to protect your finances if your job ever disappears. From building an emergency fund to making the most of employer benefits, we’ll walk you through the steps to keep your financial house in order when life throws...

Feeling stuck in your financial plan—or maybe just in life in general? Whether it’s your money, career, or day-to-day habits, a little innovation can go a long way. Today, we’re breaking down how to rethink and restructure your approach to financial planning and work-life balance using lessons from Microsoft (yes, the Xbox folks). Dean Carignan and JoAnn Garbin insights on how to build a system fo...

Love is in the air—and so are overpriced flowers, extravagant dinners, and some serious credit card regrets. In today’s episode, we tackle the financial pressure of Valentine’s Day and show you how to keep the romance alive without setting your wallet on fire. Joining us are financial pros Jesse Cramer, Sarah Catherine Gutierrez, and Len Penzo, who help us break down: The shocking reality of Valen...

Just when you thought Wall Street had run out of ways to package up risky investments and slap a shiny label on them—here we go again. Today, Joe and OG break down yet another overcomplicated, high-fee, and completely unnecessary financial product. Whether it’s preying on investor fears, promising market-proof returns, or just outright nonsense, we’ll help you spot the warning signs before you end...