The Stacking Benjamins Show

• Should You Actually Use a Catastrophic Health Plan? (& more questions from YOU!) SB1762

  Pop quiz: If your health insurance premiums keep climbing, should you just go catastrophic and pocket the savings? Joe Saul-Sehy, OG, and CFP Anna Allem tackle that exact question, along with a handful of other money decisions that keep Stackers up at night. From navigating healthcare coverage gaps to figuring out when (and how) to withdraw from a 529, this Monday mailbag episode is packed with the practical advice you need, served with the basement humor you've come to expect. The health insurance conversation gets real: what catastrophic plans actually cover (spoiler: less than you think), how to plan for the gaps, and whether gambling on your health is ever a smart financial move. Then Anna breaks down the 529 withdrawal strategy that saves you headaches at tax time, and the crew tackles a listener who's spooked by market volatility and wondering if it's time to bail. But it wouldn't be Monday without some chaos—Joe's cat decided to add drama to the morning, Doug brings trivia about counterfeit currency (because of course), and the gang updates you on the charity challenge where Stackers can support financial literacy and maybe win some prizes in the process. Plus: OG delivers movie reviews to help you figure out what's actually worth your streaming time this week. What You'll Walk Away With: • The truth about catastrophic health plans—when they make sense and when they'll leave you exposed • How to handle healthcare coverage gaps without gambling your financial future • The smart way to withdraw from a 529 so you don't accidentally trigger taxes or penalties • Why market volatility isn't a reason to panic—and what to do instead of bailing on your portfolio • How diversification and rebalancing keep you sane when the headlines get scary • A reminder that financial planning (like cat wrangling) rarely goes exactly as planned This Episode Is For You If: • You're staring at rising health insurance premiums and wondering if there's a better way • You've got a 529 but aren't sure how to actually use it without screwing up • Market dips make you nervous and you want to know if you should be doing something • You're tired of generic financial advice and want real answers to your specific questions • You believe learning about money should involve at least a few laughs (and maybe some cat stories) Got a Question for the Basement? Drop it in the comments or send it our way—you might just hear Joe Saul-Sehy, OG, and Anna tackle it in an upcoming mailbag episode. And if you want to support financial literacy while competing for prizes, check out the charity challenge details in the show. 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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• Why You Feel Broke Even When You're Doing Everything Right (SB1761)

  Ever feel like you're doing everything "right" with money—but still barely getting ahead? You're budgeting. You're saving what you can. You cut the subscriptions, meal prep on Sundays, and skip the daily latte. So why does it still feel like you're spinning your wheels? In this Greatest Hits episode, Joe Saul-Sehy welcomes Erin Lowry (Broke Millennial), Paula Pant (Afford Anything), and Greg McFarlane (Control Your Cash) to tackle the question nobody wants to ask: What if the problem isn't your spending—it's your income? Erin shares her journey from broke and stressed to financially stable and empowered, and the crew digs into why so many families struggle even when they're following all the "rules." Sometimes extreme budgeting isn't the answer. Sometimes you need to earn more. And yes, that's easier said than done—but this episode gives you the roadmap. From practical strategies for saving for retirement when cash is tight, to negotiation tricks that lower your monthly bills, to the hilariously strange side hustles people actually do for extra money (you'll never look at classified ads the same way), this conversation is packed with ideas you can use today. Plus: Classic basement banter, a "Spider Pig" serenade, Tony Romo's birthday, and all the tangents that make Stacking Benjamins feel like hanging out with friends who happen to know a lot about money. What You'll Walk Away With: • Why you might feel behind even when you're doing everything the experts tell you to do • Erin Lowry's framework for moving from "broke" to financially confident (and why it's not just about willpower) • When to focus on cutting costs vs. when to focus on earning more—and how to know the difference • Practical retirement savings strategies that work even when your cash flow is tight • Negotiation scripts for lowering your internet, phone, and other monthly bills (yes, they actually work) • Creative (and sometimes bizarre) ways people make extra money that you've probably never considered This Episode Is For You If: • You're exhausted from budgeting and feel like you're sacrificing everything but still not getting ahead • You wonder if you're just bad with money—or if something else is going on • You've cut expenses as far as they'll go and need new strategies • You're curious about side hustles but don't know where to start (or what's actually worth your time) • You need a reminder that struggling financially doesn't mean you're doing it wrong—sometimes the system is just rigged FULL SHOW NOTES: https://stackingbenjamins.com/stop-worrying-start-saving-greatest-hits-week-1761 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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• Jonathan Clements: Why Simple Beats Complicated Every Time (SB1760)

  Here's what nobody tells you about building wealth: it's not about finding the perfect investment or timing the market. It's about doing boring things consistently until they're not boring anymore—they're just your life. In this Greatest Hits episode, Joe Saul-Sehy and OG revisit a 2023 conversation with Jonathan Clements, the beloved former Wall Street Journal personal finance columnist and founder of Humble Dollar who passed away recently. We're resharing this episode to honor Jonathan's legacy, his gift for making complex ideas simple, and the joy he brought to every conversation about money. Jonathan's book, My Money Journey, features 30 real stories from real people who built financial freedom—and the lessons are surprisingly simple (which doesn't mean easy). In this conversation, Jonathan breaks down what separated the people who made it from the people who kept spinning their wheels: steady habits, ruthless simplicity, and the kind of resilience that lets you keep going when life throws curveballs. From emergency funds that actually saved people to the rent vs. buy debate that reveals more about your priorities than your budget, this conversation cuts through the complexity to show you what actually matters. Jonathan's wisdom feels even more valuable now—a reminder that the best financial advice isn't about chasing trends, it's about building a life that works for you. Joe and OG also tackle listener questions, including whether to relocate for a better job and how to balance saving for tomorrow without sacrificing today. Plus: Doug's trivia, a Key & Peele-inspired TikTok minute, and proof that the best financial teachers leave lessons that last long after they're gone. What You'll Walk Away With: • The money habits that showed up in almost every success story from Jonathan's book (spoiler: none of them are sexy) • Why simplicity beats complexity in investing—and how to stop overcomplicating your portfolio • The rent vs. buy question reframed: it's not just about math, it's about what kind of life you want • How to balance aggressive investing with the safety net you actually need (not the one Instagram tells you to have) • Why emergency funds and health insurance are the unsexy heroes of every financial success story • What "margin for error" really means—and why it's the difference between surviving setbacks and being destroyed by them This Episode Is For You If: • You're tired of chasing the next "hot" investment strategy and want to know what actually works • You feel like everyone else has figured out money except you (spoiler: they haven't) • You want to hear real stories from real people, not just theory from talking heads • You're trying to balance living well now with saving for later—and feeling stuck in the middle • You believe the best teachers are the ones whose lessons outlive them 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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• What a 12-Hour Walk Teaches You About Money (And Life) SB1759

  Here's a wild idea: What if the thing holding you back isn't your bank account, your age, or your circumstances—it's just the story you've been telling yourself? Joe Saul-Sehy and OG sit down with Colin O'Brady, four-time world record holder and endurance athlete who's done things most people would call impossible: solo trek across Antarctica, row across the Drake Passage, and yes, take a 12-hour walk that changed his entire perspective on what humans are capable of. Colin's not just here to tell adventure stories (though those are incredible). He's here to talk about the mental game—the part where you convince yourself to take the first step even when the finish line seems impossibly far away. Sound familiar? Whether you're staring down a cross-country expedition or trying to figure out if you'll have enough saved for retirement, the challenge is the same: push past the voice that says "I can't" and prove to yourself that you can. Then Joe and OG bring it back to the basement with a listener question about Roth vs. Traditional 401(k) contributions—because financial endurance is just as important as physical stamina. They break down how to think long-term about taxes, flexibility, and building a retirement plan that actually fits your life. Plus: Neighbor Doug delivers trivia that proves even world record holders have to earn their laughs in the basement. What You'll Walk Away With: • What Colin O'Brady's 12-Hour Walk reveals about breaking through your mental limits (and how it applies to money decisions too) • The mindset shift that separates people who attempt big goals from people who actually achieve them • Smart strategies for balancing Roth and Traditional 401(k) contributions based on your timeline and tax situation • Why flexibility matters as much as discipline—whether you're planning an expedition or planning retirement • Permission to set goals that scare you a little (because that's usually where the good stuff happens) This Episode Is For You If: • You've been telling yourself you "can't" do something but wonder if that's actually true • You want inspiration that comes with actual tactics (not just motivational fluff) • You're trying to figure out the Roth vs. Traditional 401(k) question and want a clear answer • You believe your best life is out there, but you're not sure how to build toward it • You need a reminder that big transformations start with small, intentional steps FULL SHOW NOTES: https://stackingbenjamins.com/conquer-your-mount-everest-greatest-hits-week-1759 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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• What Retirees Wish They'd Known 10 Years Ago (SB1758)

  Want to know what keeps retirees up at night? It's not what they did—it's what they wish they'd done ten years earlier. Joe Saul-Sehy is joined by Jill Siriani (Frugal Friends), Jesse Cramer (The Best Interest), and Doc G (Earn & Invest), who all pull up chairs in the basement for a powerhouse roundtable on the five regrets that show up again and again when people hit retirement. These aren't hypothetical "what-ifs"—they're real stories from a real CFP, sharing tales about people who wished someone had told them sooner. From botched investment allocations that left people either too risky or too conservative, to tax mistakes that cost tens of thousands, to the heartbreaking pattern of people who saved everything but never actually enjoyed their money—this conversation gets real about what actually matters when you're trying to retire with confidence (and joy). The good news? Every single one of these regrets is avoidable. The panelists share what to do now so you don't become one of these stories later, including the estate planning moves that take ten minutes but save your family years of headaches, and why the biggest retirement regret isn't financial at all—it's emotional. Plus: Doug's trivia challenge pits the panel against each other for bragging rights, because even serious money talk deserves a little competition. What You'll Walk Away With: • The five regrets that show up over and over in retirement—and the specific moves that prevent each one • Why your investment allocation in your 40s and 50s might be setting you up for regret in your 60s • Tax strategies that keep more money in your pocket (because giving Uncle Sam extra is nobody's retirement dream) • The simple estate planning steps most people skip—and why your family will thank you for not skipping them • How to give yourself permission to actually enjoy your money instead of hoarding it out of fear This Episode Is For You If: • You're decades from retirement but want to avoid the "I wish I'd known" moments • You're closer to retirement and worried you've missed something important • You want to hear top financial minds debate what actually matters (spoiler: they don't always agree) • You're tired of generic retirement advice and want to hear what real retirees actually regret • You believe retirement should be about living well, not just having enough FULL SHOW NOTES: https://stackingbenjamins.com/top-5-retirement-plan-regrets-1758 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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