The Stacking Benjamins Show

• The Stuff You Should Stop Buying (and Why Your Wallet Will Thank You) SB1707

  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’s Most Unexpected Influencer”). Together, they go head-to-head in a raucous showdown, each offering hot takes on everyday items you should stop buying if you want to save money and ditch the clutter. We dig into: Why some exercise equipment becomes expensive coat racks The hidden costs of seasonal decorations Periodicals, subscriptions, and other budget vampires And a few “who knew?” items that quietly drain your cash You'll also get a dose of trivia, debates about Google's "search decay," and a few personal stories that might sound a little too familiar. Whether you’re decluttering your budget or just here for the basement chaos, this episode is full of laughs, lightbulb moments, and ideas to help streamline your spending. FULL SHOW NOTES: https://stackingbenjamins.com/decluttering-your-financial-life-greatest-hits-1707 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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• Happy Money, Hidden Fees, and Hiring Your Kids (SB1706)

  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 can lead to big life changes. But before we get zen with our Benjamins, Joe and OG shine a light on the latest investigation into real estate commissions. Are hidden fees quietly draining your wallet when you buy or sell a home? The Justice Department seems to think so. We dive into what’s happening—and what you can do about it. Also in the episode: HSA contribution limits are rising—are you using your health savings account the smart way? A listener wonders if hiring their kids can unlock Roth IRA opportunities (spoiler: it’s not as simple as “just write them a check”). Doug moonshines a trivia question that may or may not involve death (but definitely involves Doug). Whether you’re looking for practical strategies or a new perspective on money itself, this episode brings both insight and inspiration. FULL SHOW NOTES: https://stackingbenjamins.com/happiness-with-ken-honda-greatest-hits-1706 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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• Want More Money? Cut The Clutter (with Tracy McCubbin) SB1705

  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 Social Security too early. Timing isn’t just everything—it’s the difference between thriving in retirement and wondering where all the money went. In this episode, we cover: Why sentimental clutter is more than just "stuff"—and how to finally let it go. How donating intentionally can breathe new life into your old things (and clear some mental space). The tough conversations adult kids need to have with parents about downsizing and letting go. Strategies to help you avoid making costly Social Security decisions. A surprisingly thoughtful take on the Taco Bell Hotel (yes, it’s real... and yes, it sold out in minutes). Plus: a listener question, some truly questionable fashion choices, and one more reason not to hoard your retirement benefits—or your holiday dishes. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Let's Start a Money Revolution (SB1704)

  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 coach, shares how she raised her financial flag as a single mom and became a force for smart money choices. Jesse Cramer of the Personal Finance for Long-Term Investors podcast ditches tired spending habits and charts a course for independence through intentional investing and budgeting. Steve Stewart, longtime SB editor and podcasting Yoda, reveals the pivotal Jeep moment that changed his financial course—and why he's racing OG to mortgage freedom. 🎙️ In this basement-based revolution, you'll hear: The financial “tea party” moments that woke our guests up to their money mess How to declare independence from credit cards, lifestyle creep, and sneaky “Buy Now, Pay Later” traps Tools, mindsets, and support systems that help you keep your financial revolution alive Why tax planning is the financial Boston Tea Party nobody's talking about The trivia showdown no revolutionary should miss: How many grains of silver made a dollar in 1792? (Spoiler: Jesse knows his colonial coinage.) And in the aftershow? We ask the deep questions our Founding Fathers never saw coming, like: why is gambling debt dischargeable in bankruptcy, but student loans aren't? FULL SHOW NOTES: https://stackingbenjamins.com/financial-independence-day-2025-1704 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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• Turning Ideas into Billion Dollar Businesses (with Julie Wainwright) SB1703

  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 what it really means to build something new when everyone else is telling you no. From the boardroom to the resale boutique, she takes us through the emotional rollercoaster of entrepreneurship—plus a few secrets on why luxury goods are more than just a pretty label. Also in the basement: We unpack Jason Zweig’s latest Wall Street Journal column on diversification and why it still matters (yes, even in this market). OG learns a Father’s Day lesson on the golf course (spoiler: not all swings are created equal). Doug manages to work in Margot Robbie. Again. Whether you’re plotting your own business empire or just wondering how someone not only recovers from flaming sock puppet-level failure, but who THRIVES afterward, this episode delivers honest insight with a side of style. FULL SHOW NOTES: https://www.stackingbenjamins.com/from-business-idea-to-execution-julie-wainwright-1703/ 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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