Episodes

  • Top 5 Eye-Roll Financial Tips You Should Ignore SB1664

    Top 5 Eye-Roll Financial Tips You Should Ignore SB1664
    Apr 2 2025
    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 about extreme couponing, bad budgeting ideas, and the wild world of TikTok money myths, this episode is your roadmap to not falling for advice that sounds smart but… absolutely isn’t. In this episode: Why “buying big” won’t necessarily inspire you—it might just bankrupt you Skipping insurance to save money? We’ll show you how that plan ends Should couples really share just one checkbook? We investigate The great emergency fund vs. credit card debate When DIY everything turns into Why Did I Try? How the satire in The Joneses movie is secretly more real than you think Listener Q&A: Impact investing, private debt financing, and what it means to be an accredited investor Plus, a surprise TikTok moment, OG's thoughts on calendars, Doug’s history of April Fools’ disasters, and much more You’ll laugh, you’ll learn, and by the end, you’ll be a whole lot more confident dodging bad advice in the wild. 🎧 Tune in and stack smarter by skipping the “advice” that could sink your stack. FULL SHOW NOTES: https://stackingbenjamins.com/our-top-five-money-saving-solutions-1664 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy!  Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 14 mins
  • Tiffany Aliche on Connections and Financial Wholeness (with a side discussion on recent DoorDash/Klarna news) SB1663

    Tiffany Aliche on Connections and Financial Wholeness (with a side discussion on recent DoorDash/Klarna news) SB1663
    Mar 31 2025
    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 equivalent of eating fast food in your car—feels great now, but you’ll regret it later—and how even a trip to Texarkana can teach you a thing or two about money. Plus, a story involving World War II espionage that somehow made its way into the mix. Here’s what’s on tap this week: Kicking off Monday with a solid dose of grumpiness (and a passionate store-brand rant). Hanging with The Budgetnista—Tiffany Aliche takes us behind the scenes. Why financial literacy isn’t just about numbers—it’s about community. The sneaky financial traps that might be eating your wallet alive. Tiffany’s PBS special—how she tackled stage fright and delivered a knockout show. Headlines that made us go “Wait, WHAT?!”—including Klarna and DoorDash teaming up. ‘Buy Now, Pay Later’—why it’s like borrowing money from Future You (and Future You is not happy about it). Mortgage strategies, financial independence, and the art of dodging debt. Could you survive a week on cash only? One of us is trying (and maybe crying). Food waste: it’s not just bad for the planet—it’s silently draining your bank account. Upcoming meetups, tax tips, and basement-style money wisdom you can actually use. And if you stick around long enough, well… who knows what else might show up? FULL SHOW NOTES: https://stackingbenjamins.com/budgetnista-financial-literacy-1663 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 14 mins
  • Better Investing Using Horrible Investment Products (SB1662)

    Better Investing Using Horrible Investment Products (SB1662)
    Mar 28 2025
    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 Talking Real Money. Infinite banking and other shiny traps – What sounds like genius often comes with fine print you’ll wish you’d read. Penny stocks and the illusion of easy money – Spoiler: if it feels like a shortcut, it's probably a detour. Equity-indexed annuities and their slick sales tactics – When someone tells you there’s “no downside,” maybe run. Gut feelings vs. data – The panel weighs in on trusting instincts vs. trusting actual math. Teachers and 403(b) plans – A quick peek behind the curtain at one of the most overlooked problem areas in personal finance. How not to invest – A rundown of red flags and hard-won wisdom from people who’ve seen the worst up close. Meanwhile, Doug brings the trivia thunder with a question about sitcom salaries—and things quickly go from Big Bang to big bucks. Whether you’ve made a misstep or are just trying to avoid one, this episode will help you tune out the noise, spot the nonsense, and build a smarter, more resilient investment plan. FULL SHOW NOTES: https://stackingbenjamins.com/our-least-favorite-investments-1662 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 5 mins
  • How NOT To Invest: Lessons from Barry Ritholtz SB1672

    How NOT To Invest: Lessons from Barry Ritholtz SB1672
    Mar 26 2025
    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 his years in the trenches, covering everything from behavioral finance to market psychology and how to avoid falling for trends that make great headlines but terrible portfolios. Also in this episode: Subscription hacks you didn’t know you needed (and yes, even that one you've been ignoring since 2021). How market history can be your secret weapon—if you actually pay attention to it. Tech innovations in finance and why Barry says they're both exciting and a little terrifying. Productivity gains, AI, and whether the future is a robot that trades ETFs for you while you nap. A peek into Barry’s latest book and the big idea that might shift how you think about investing. Doug creates yet another national holiday—because what the world needs now is Bow Chicka Wow Wow Day. Stacker mailbag time! We’re diving into job loss strategies, building bulletproof emergency funds, and yes, getting into the weeds with buffer ETFs. The never-ending showdown: remote work vs. office life—where do Stackers land? And of course, Doug’s trivia will challenge your financial knowledge and possibly your respect for faux holidays. Whether you’re a seasoned investor or just now figuring out what a 401(k) actually does, this episode brings the insight, laughs, and community you’ve come to expect from the basement. 🎧 Tune in and stack smarter—with fewer missteps and a whole lot more fun. FULL SHOW NOTES: https://stackingbenjamins.com/getting-your-investments-right-with-barry-ritholtz-1661 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 18 mins
  • 10 Ways to Stop Blowing Up Your Investment Portfolio (SB1660)

    10 Ways to Stop Blowing Up Your Investment Portfolio (SB1660)
    Mar 24 2025
    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 emotions in check, Barry’s top 10 tips serve up the kind of grounded, no-BS advice your portfolio will thank you for—especially the next time the market gets jumpy or the headlines go haywire. They also tackle what politics really mean for your investments (spoiler: maybe less than you think) and why getting your expectations right could be the most important investment decision you make. Stick around to hear a listener question that hits close to home: How should you invest for an 84-year-old mom? It’s a multigenerational money moment that brings the discussion full circle. Here’s what you’ll learn: Why market cycles matter (and how to avoid getting whiplash) The hidden dangers of investing with your heart instead of your head What Barry Ritholtz says about predicting political impacts on your portfolio How to set realistic return expectations (and why that’s surprisingly freeing) A practical investing strategy for elderly parents—without the jargon Plus: Doug’s trivia takes a nostalgic turn into the wild world of Beanie Babies FULL SHOW NOTES: https://stackingbenjamins.com/how-not-to-invest-1660 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 7 mins
  • How Pros Build Motivation Into an Effective Financial Plan (SB1659)

    How Pros Build Motivation Into an Effective Financial Plan (SB1659)
    Mar 21 2025
    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 motivated is harder than it looks—and how to actually keep yourself on track, even when life (or a killer sale on Amazon) tries to derail you. We’ll explore why people resist financial planning (hint: it’s not always laziness), how goal-setting psychology plays into money habits, and why tracking your finances can be as powerful as tracking your fitness. Dana shares the surprising link between logging your retirement balance and saving more, while OG and Jesse tackle the age-old debate: should financial advisors be more like sports agents—pushing, coaching, and sometimes delivering the tough love? Plus, we dig into why writing things down actually works (seriously, it’s science) and how a simple mindset shift can help you finally take action. And of course, what’s a Friday without Doug’s trivia? This week, Doug takes us back to the boxing ring with a question about the legendary Joe Louis—and the sucker punch that is junk fees. ? Our roundtable throws their best guesses into the ring, but who will come out on top? Play along and see if you can take home the trivia belt! This was a great finish to a week of talking motivation and drive! From the seven steps to dynamic drive to sports agent Molly Fletcher on Wednesday and this discussion, it's a well-rounded week that should help you get up and go...even if you think YOUR get up and go got up and went. FULL SHOW NOTES: https://stackingbenjamins.com/motivation-habits-and-planning-1659 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 5 mins
  • Climb Out of Your Rut: Molly Fletcher on Creating Sustainable Motivation (SB1658)

    Climb Out of Your Rut: Molly Fletcher on Creating Sustainable Motivation (SB1658)
    Mar 19 2025
    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 energy to embracing adversity like a pro. But wait, there’s more! Len Penzo (yes, of LenPenzo dot com fame!) joins us as guest co-host, bringing his usual mix of wisdom, dry wit, and probably a few thoughts on sandwich prices. And if you think motivation is tough, try navigating the world of credit—because while ambition is great, bad credit can still trip you up. From student loan pitfalls to practical credit repair tips, we cover what younger folks (and honestly, all of us) need to know about keeping those numbers in check. In this episode: Molly Fletcher on Peak Performance – Lessons from a top sports agent on how to stay motivated without burning out. Complacency vs. Contentment – Are you stuck or simply satisfied? Molly breaks it down. Managing Energy Like a Pro – Tom Izzo swears by it, and so should you. Credit Crash Course – What happens when student loans go delinquent, and how to fix the damage. The Living Without Credit Debate – Is a debt-free life possible, or just a financial myth? Doug & OG’s Ski Slope Disaster – A story of poor decisions, gravity, and bruised egos (hilarious in retrospect). Len Penzo's Tips for Improving Credit Scores – Because nobody budgets quite like Len. Whether you need a motivation boost, a credit check-up, or just a good laugh at Doug’s expense, this episode has you covered. 🎧 Tune in for wisdom, financial hacks, and some après-ski storytelling you won’t want to miss! FULL SHOW NOTES: https://www.stackingbenjamins.com/find-your-dynamic-drive-molly-fletcher-1658/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 22 mins
  • How to Use Process to Create Sustainable Drive (SB1657)

    How to Use Process to Create Sustainable Drive (SB1657)
    Mar 17 2025
    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 ready to hit the ground running when we welcome former sports agent Molly Fletcher on Wednesday. 💰 In this episode: Why motivation fizzles out—and how to make it last The seven keys to Dynamic Drive (and how to apply them to your finances) How milestones and energy management keep you on track Tax strategies for selling shares—FIFO, LIFO, or average cost? Which method helps you keep more of your hard-earned Benjamins? What cowboy fencing teaches us about peak performance (yes, that’s a thing) Plus, Doug serves up a sports trivia challenge—because what’s financial motivation without a little fun? 👉 Listen in now and get fired up—without burning out! FULL SHOW NOTES: https://stackingbenjamins.com/how-to-create-a-sustainable-drive-1657 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 hr and 8 mins