The Stacking Benjamins Show

You just came into $50,000—no strings attached. Do you crush your debt? Supercharge your retirement? Blow it all on a podcasting-themed backyard grotto? In this episode of The Stacking Benjamins Show , Joe Saul-Sehy , OG , Paula Pant (Afford Anything), and Jesse Cramer (The Best Interest) gather around the card table in Mom’s basement to tackle one of the most common “someday” questions in persona...

High school math left most of us staring blankly at the board, convinced compound interest was just a fancy way to say "confusing." But what if math could be fun, relevant, and—dare we say—life-changing? In this episode of The Stacking Benjamins Show , Joe Saul-Sehy , OG , and Neighbor Doug welcome economist, education reformer, and documentary filmmaker Ted Dintersmith to the basement for a conve...

Big changes are coming to the tax code—and that could mean big savings if you know where to look. On today’s episode, Joe, OG, and Doug break down the most important updates in the 2025 tax laws and share smart, simple ways to keep more of your hard-earned cash. Whether you're a spreadsheet-loving tax nerd or someone who still asks, “Wait, do I have to file?”—this episode will help you navigate th...

What if the scariest part of retirement isn’t running out of money—but losing your sense of identity? This week on The Stacking Benjamins Show , we tackle the fears that hold so many people back from financial independence and a joyful, purpose-filled retirement. Joe Saul-Sehy and Doug are joined by an all-star panel of financial thinkers: Mark Trautman ( Mark’s Money Mind ) Paula Pant ( Afford An...

What do your financial priorities look like when you're just getting started... or when you're sitting on $100 million? If you’re still stuck trying to figure out how to max out your Roth IRA and also afford dinner, this episode’s going to walk you through what might be coming next—without promising you a yacht by Tuesday. This week on The Stacking Benjamins Show , Joe Saul-Sehy , O.G. , and Doc G...

What’s the right financial move for you… right now? If you've ever found yourself reading advice meant for a millionaire when you're still trying to crack five figures—or following budgeting tips when your net worth is seven digits—this episode is your custom-tailored financial GPS. In this installment of The Stacking Benjamins Show , Joe Saul-Sehy, OG, and Doug take you rung-by-rung through the w...

Ever feel like you're working hard but getting nowhere? You're not alone—and you might be stuck in a productivity trap, not a purpose-driven plan. In this episode of The Stacking Benjamins Show , we tackle the big one: how to avoid wasting your life. (No pressure.) Joe Saul-Sehy kicks things off with a tongue-in-cheek nod to all the ways we fritter away time—before pivoting into a power-packed con...

Want to crush your goals and avoid getting crushed by long-term care costs? In today’s episode of The Stacking Benjamins Show , Joe Saul-Sehy and OG are joined by Retired Lieutenant Commander Gary McDermott , a former U.S. Navy officer turned business coach, who brings military-grade discipline to the world of goal-setting and financial success. Whether you’re working toward a promotion, launching...

Still on track to crush your 2025 goals? Or has the year felt more like a Super Mario Kart banana peel moment? In this special mid-year review episode of The Stacking Benjamins Show , Joe Saul-Sehy and OG take a pause from the summer sprint to look back at the most impactful lessons, conversations, and themes from the first half of 2025. Whether you’re rethinking your budget, fine-tuning your risk...

Is your house full of stuff you thought you needed… but haven’t touched since the Obama administration? In this game show-style episode, we're helping you clean house and bulk up your bank account at the same time. Joining Joe in the basement are Paula Pant from Afford Anything , OG, and the man, the myth, the TikTok-famous legend’s grandpa’s best friend: Len Penzo (or as Doug calls him, “America’...

What if your money could bring you more joy—and less stress? Today, we welcome Ken Honda, Japan’s bestselling personal development guru, to the basement. He introduces us to his concept of “Happy Money,” where gratitude replaces fear, and your relationship with money becomes… well, happier. From early lessons in emotional finance to wisdom from his own mentors, Ken shares how small mindset shifts...

Is your home packed with emotional baggage... and maybe a few fondue sets you haven’t touched since 2003? Organizational expert Tracy McCubbin joins us to talk about the emotional side of clutter—why it builds up, how it weighs us down, and what to do when your sentimental stuff is quietly running the show. Meanwhile, Joe and OG dig into another kind of mess: the billions retirees lose by claiming...

Happy Independence Day, Stackers! While fireworks boom and flags wave, we're lighting a spark under your financial life. This episode isn’t about tea in harbors—it’s about burning down debt, revolting against lifestyle creep, and rallying your family for a better money future. Joining Joe and Doug in the basement for this full-on financial insurrection: Dorethia Kelly , TikTok titan and money coac...

What does it take to turn a bold idea into a billion-dollar brand? Julie Wainwright, founder of The RealReal, joins us to share how she did just that—after enduring some pretty public failures (hello, Pets.com). She talks about navigating the startup world, tackling ageism head-on, and why your past doesn’t define your future. Julie’s story is packed with wisdom on risk-taking, confidence, and wha...

How much can you really spend in retirement without running out of money—or worse, running out of fun? In this deeper-than-usual dive, Joe Saul-Sehy and OG examine the classic 4% retirement rule and whether it’s time for an upgrade. With new commentary from Bill Bengen, the original architect of the 4% rule, the team explores emerging research that suggests a withdrawal rate closer to 5.5% might b...

Can you really build wealth with a simple formula? Do you need a budget to succeed financially? Should you cut up all your credit cards, or is that just a dramatic TikTok trend? In this episode of The Stacking Benjamins Show , Joe Saul-Sehy is joined by Paula Pant, Doc G (Jordan Grumet), and Jesse Cramer for a roundtable discussion that peels back the truth behind popular advice from so-called fin...

What’s the best way to save for a house without wrecking your retirement plan? That’s just one of the big questions Joe Saul-Sehy, OG, and Mom’s neighbor Doug tackle in this packed episode (number 1700!) of Stacking Benjamins . Whether you're trying to figure out where to park your emergency fund, how to handle inherited IRAs, or how to financially plan as a single adult with big responsibilities...

The robots aren’t just coming—they’re already here. And if you’re not paying attention, they might not just take your job… they could take your personal data too. In this episode of The Stacking Benjamins Show , Joe Saul-Sehy, OG, and Doug dive into the rise of artificial intelligence, exploring whether it’s a threat, a tool, or something in between. If you’ve been wondering how AI will impact you...

So you’ve scaled the mountain, built the nest egg, and maybe even shouted “I’m done!” across a pristine beach... now what? In today’s Stacking Benjamins episode, Joe Saul-Sehy convenes a roundtable of heavy-hitters to tackle the most misunderstood phase of money management: decumulation —a.k.a. the art of spending what you’ve worked so hard to save. Whether you're staring down retirement or alread...

What if the most important part of your retirement plan had nothing to do with your 401(k), IRA, or stock portfolio? In this episode of The Stacking Benjamins Show , Joe Saul-Sehy and OG are joined by filmmakers Pete Davis and Rebecca Davis, creators of the thought-provoking documentary Join or Die . They explore how community connection, not cash, may be the ultimate retirement strategy . Drawing...

You can’t plan a great retirement if you haven’t first planned what you’re retiring to. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug open up Retirement Week in the basement with a Monday that’s equal parts insight, weekend recap, and questionable vehicle decisions. 🚪 Start with the most overlooked part of retirement: your lifestyle vision . What are you actually going to do all day—and w...

Markets crashing? Interest rates spiking? Inflation roaring? Welcome to history. This week, we dig into 130 years of stock market meltdowns—from the panic of World War I to the Great Depression, 1970s stagflation, the dot-com collapse, and the 2008 financial crisis—to uncover timeless lessons that can fortify your financial future. Joe Saul-Sehy is joined by Miranda Marquit , Jesse Cramer , and OG...

What happens when you mix financial strategy with a healthy dose of cultural commentary? You get Rich Girl Nation. This week on The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Katie Gatti Tassin, the powerhouse behind Money with Katie and author of the new book Rich Girl Nation . Together, they unravel the sneaky ways consumerism shows up in our lives—from pricey trends to status-s...

Is your wallet feeling lighter... but your closet’s full of regret? Joe, OG, and Mom’s neighbor Doug are throwing open the basement door to tackle one of the trickiest parts of personal finance: consumerism . Whether you're a recovering impulse buyer or knee-deep in buy-now-pay-later regrets, this episode’s got your back—and maybe your budget. 💸 Hear real stories about overspending and why value-...

Can building wealth be as entertaining as a round of trivia in the basement? We think so—and today’s episode proves it. Joe Saul-Sehy is joined by Doc G, Paula Pant, and Jesse Cramer to play a fast-paced financial game show based on 11 expert-approved ways to grow your wealth. From boosting your income and dialing in your budget to the eternal tug-of-war between paying down debt and investing more...