The Stacking Benjamins Show

• Does More Money Actually Make Life Easier? (Spoiler: Not Really) SB1773

  Does more money make life easier, or does it just give you more expensive problems to solve? Most people assume that once they start earning more, their financial life will finally calm down and organize itself. Then they get the raise or the promotion or the business success, and somehow things feel just as chaotic as before, just with bigger numbers involved. Joe Saul-Sehy is joined by Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and OG to explore why "more" isn't always "simpler." The crew digs into early money mistakes they'd all like to forget, the weird psychological traps that show up as income grows, and why your brain doesn't automatically upgrade its money management skills just because your paycheck did. The conversation gets real about the hidden mental challenges that come with wealth growth. Decision fatigue gets worse, not better. Lifestyle creep sneaks in wearing a very convincing disguise. And suddenly you're agonizing over choices that used to be simple, because now you can afford multiple options and none of them feel obviously right. If you've ever wondered why your financial life didn't magically self-organize the moment you started earning more, this roundtable has your answers. The crew also tackles listener questions about building budgeting habits that actually stick, finding genuine financial confidence, and creating systems that scale with your life instead of working against it. Because the goal isn't just to make more money. It's to build a life that feels manageable and intentional at whatever income level you're at. Plus, Doug delivers a trivia showdown featuring fierce competition, questionable strategy, and what might be the most overthought trophy dilemma in basement history. What You'll Walk Away With: • Why more income doesn't automatically reduce financial stress and often creates new complications • The hidden mental traps people fall into as their wealth grows and how to spot them early • How Paula, Jesse, OG, and Joe think about building lasting financial confidence at any income level • Practical budgeting strategies that work whether you're making $50K or $500K • Why simple pleasures matter more (not less) as your money grows • The surprising ways earning more actually complicates everyday decisions • Listener Q&A on habits, organization, and creating systems that smooth out financial chaos • Permission to admit that making more money didn't solve everything like you thought it would This Episode Is For You If: • You're earning more than you used to but somehow don't feel more in control • You assumed financial stress would decrease with income but it just shifted to different problems • You're stuck between multiple good options and can't figure out why that's so paralyzing • You want to hear successful people admit that more money created complications they didn't expect • You're building wealth but want to make sure you're also building a life that feels good Before You Hit Play, Think About This: What's one financial decision that got harder (not easier) as you started earning more money? Drop your answer in the comments because this roundtable proves you're definitely not the only one experiencing this paradox. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Magic and Logic: How Lew Frankfort Built Coach (Plus: Don't Make This Retirement Mistake (SB1772)

  Walking away from a secure city government job to eventually run one of the world's most recognizable handbag brands sounds like fiction. For Lew Frankfort, it became his career story, and the path between those two points is exactly what makes this conversation so valuable. Lew joins Joe Saul-Sehy and OG in the basement to break down how a combination of discipline, curiosity, and what he calls "magic and logic" shaped his journey from city hall to the corner office at Coach. This isn't just inspiration for aspiring executives. Lew's insights about making better decisions, taking calculated risks, and building a meaningful life apply whether you're 25 or 55, whether you're climbing the ladder or considering jumping to a different one entirely. Lew shares how preparation became his secret advantage, why curiosity beats confidence during major transitions, and what he learned about leadership while helping transform Coach into a global powerhouse. His framework for balancing intuition with analysis gives the Confident Explorer a practical lens for evaluating their own big moves, career pivots, or midlife reinventions. Then Joe and OG shift gears to tackle a different kind of transition. The first year of retirement. When excitement runs high and "go-go" energy meets newfound freedom, spending can spiral in ways that derail decades of careful planning. They break down the crucial financial decisions retirees face right out of the gate, why that first year can be surprisingly dangerous, and how to set yourself up for long-term stability without killing the joy of finally having time to live. Plus, Doug delivers trivia involving time travel and underwear, because even episodes about CEO wisdom and retirement planning need a reality check from the basement. What You'll Walk Away With: • How Lew Frankfort pivoted from city government work to leading Coach and what that path teaches about career reinvention • The "magic and logic" framework anyone can apply to big decisions and career moves • Why curiosity and thorough preparation matter more than confidence when making your next leap • Leadership lessons from someone who helped build a global brand from the inside • What retirees absolutely must understand about spending during that crucial first year • Why the "go-go years" of early retirement can wreck your finances if you're not careful • Strategies for aligning your early retirement excitement with long-term financial stability • Permission to reinvent yourself at any age, armed with both inspiration and practical wisdom This Episode Is For You If: • You're considering a career change but worried you're too far along to pivot • You want to understand how successful people actually made their big moves • You're approaching retirement and want to avoid the spending traps that catch most people • You're curious how to balance intuition with analysis when making major life decisions • You believe it's never too late to build something meaningful or try something new Before You Hit Play, Think About This: What's one career move or life transition you've been thinking about but haven't pulled the trigger on yet? What's actually holding you back? Drop your answer in the comments because Lew's story might be exactly the perspective shift you need to take that next step. FULL SHOW NOTES: https://www.stackingbenjamins.com/https-stackingbenjamins-com-lou-frankfort-bagman-1772/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 (https://www.stackingbenjamins.com/201) Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• How to Actually Enjoy Holiday Small Talk (And Give Better Gifts for Less) SB1771

  Holiday parties make you want to hide behind the cheese tray. Gift-giving season makes your budget cry. This episode is your survival guide for both. Joe Saul-Sehy, OG, and Neighbor Doug welcome Pulitzer Prize-winning author Charles Duhigg to turn holiday small talk from awkward endurance test into something you might actually enjoy. Whether you're facing the office party, a family gathering with that cousin who won't shut up about crypto, or the neighborhood potluck where you know exactly three people, Charles reveals how to walk into any room with confidence, even if you're an introvert who'd rather be home watching movies. The secret? Super communicators aren't the loudest people in the room. They're the ones asking better questions, reading the conversation correctly, and making others feel heard. Charles breaks down the skills that turn painful small talk into genuine connection, and why introverts actually have hidden advantages at holiday gatherings (yes, really). Then the crew tackles the other holiday stressor of gift-giving that doesn't demolish your December budget. Joe, OG, and Doug explore the rising trend of secondhand gifting. It's not just about saving money (though your wallet will thank you). It can be more meaningful, more creative, and kinder to both your finances and the planet. From thrifted treasures to thoughtful "found" gems, they share how to give smarter instead of just spending more. Plus, Doug's toilet paper trivia arrives right on schedule (because what's a holiday episode without something unexpected?), along with stories about neighbors behaving badly and a brief tour through apps you forgot you're still paying for. What You'll Walk Away With: • Charles Duhigg's framework for turning small talk into actual connection without feeling fake • Why introverts have secret advantages at holiday parties and how to use them • Smart, budget-friendly gifting strategies that feel thoughtful rather than last-minute or cheap • The case for secondhand gifts and how to do it in a way that feels special • How to avoid blowing your holiday budget without looking (or feeling) stingy • Creative ways to personalize gifts without overspending or resorting to gift cards • Why communication skills affect both your happiness and your financial decisions This Episode Is For You If: • Holiday small talk feels like torture and you'd rather shovel snow • You want to give meaningful gifts but refuse to wreck your January budget doing it • You're an introvert dreading the season of forced social interaction • You're tired of generic gift guides telling you to "just spend less" without actual ideas • You believe better conversations and smarter spending are both learnable skills Before You Hit Play, Ask Yourself: What's the most meaningful non-new gift you've ever given or received? Think about why it mattered. That's the kind of gifting Charles and the crew are talking about. Drop your story in the comments because we're building the anti-Amazon holiday gift playbook together. FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-actually-enjoy-holiday-small-talk-1771/ 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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• How to Save Money Without Making Your Life Miserable (SB1770)

  Here's the problem with most frugality advice: it makes you feel like a monk who's taken a vow of joylessness. Joe Saul-Sehy and Neighbor Doug gather the roundtable crew—Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and Andy Hill (Marriage, Kids, and Money)—to prove that frugality isn't about deprivation. It's about designing a life that feels good and costs less. The conversation gets real fast: what's the difference between thoughtful frugality and soul-crushing penny-pinching? How do you cut spending without cutting joy? And why do some people thrive on frugal challenges while others just end up resentful and burnt out? The crew shares their own tactics, from "shopping your fridge" (a shockingly high-ROI habit most people ignore) to the power of frugal sprints instead of permanent deprivation mode. They break down how to align your spending with your actual values instead of society's expectations, why raising income often beats shaving another $3 off your grocery bill, and how to turn frugality into something your kids actually want to participate in (no guilt trips required). You'll also hear about the expenses each of them refuses to cut no matter how frugal they get, because smart money management isn't about eliminating everything; it's about keeping what matters and ditching what doesn't. Plus: stories about mystery freezer leftovers, subscription fees that sneak in like cat burglars, and Doug's perspective on... well, whatever Doug decides matters that day. What You'll Walk Away With: • The difference between frugality that improves your life and penny-pinching that just makes you miserable • Why "shopping your fridge" might be the highest-return grocery habit you'll ever adopt • How to design spending around your actual values instead of just cutting blindly • The power of "frugal sprints"—short-term challenges that work without long-term burnout • How to involve your kids in frugal habits without making them feel deprived • Why focusing on raising income often matters more than obsessing over tiny budget cuts • Which expenses the pros refuse to cut—and why knowing your "worth it" list matters This Episode Is For You If: • You want to save money but refuse to live like you're broke when you're not • Traditional frugality advice makes you feel guilty about things that actually bring you joy • You're trying to cut spending but can't figure out where to start without feeling deprived • You want to model smart money habits for your kids without making them fear spending • You're tired of finance advice that assumes everyone should want the same lifestyle Before You Hit Play, Think About This: What's the one expense you refuse to cut, no matter how frugal you get? And what does that tell you about what actually matters to you? Drop your answer in the comments—we want to know what's on everyone's "worth it" list. FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-save-money-without-making-your-life-miserable-sb1770/ 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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• Morgan Housel: Why You Spend Money (And How to Do It Better) SB1769

  Here's something nobody tells you: knowing how to make money is easy compared to knowing how to spend it well. Morgan Housel, bestselling author and one of the sharpest minds in personal finance, is back in the basement with Joe Saul-Sehy, OG, and Neighbor Doug to tackle the question most financial advice completely ignores: why do we spend the way we do, and how can we get better at it? This isn't about budgeting apps or cutting lattes. It's about understanding the psychology underneath every swipe of your card. Morgan shares stories from his early days working valet for the ultra-wealthy—the spending patterns he observed, the misery he witnessed, and the lessons that changed how he thinks about money forever. Turns out, having more money doesn't automatically make you better at spending it. In fact, it often makes you worse. The conversation digs into what actually creates happiness (spoiler: it's not more stuff), why contentment matters more than your net worth, and how true financial independence isn't about the size of your portfolio—it's about the freedom to make choices that align with your actual values. Morgan also breaks down what Warren Buffett's retirement announcement reveals about staying grounded while building wealth, and why comedians might understand money better than most economists. Plus: Doug takes a trivia detour to a surprisingly risqué national park (because of course), and the crew wraps with binge-worthy recommendations for your next couch night. If you're tired of chasing more and ready to figure out what enough actually looks like, this episode is required listening. What You'll Walk Away With: • Why spending money well is a psychological skill, not a math problem—and how to develop it • What Morgan learned about wealth and misery from parking cars for millionaires in their driveways • The hidden drivers behind your financial decisions (and how to spot them before they derail you) • Why contentment—not consumption—is the real key to long-term happiness • What true financial independence actually means (hint: it's not a number in your bank account) • How Warren Buffett's approach to retirement reveals timeless principles about money and legacy • Simple guiding principles to help you spend smarter and live calmer This Episode Is For You If: • You've hit financial goals but still don't feel satisfied • You're tired of spending money on things that don't actually make you happier • You want to understand why you make the money decisions you do (even the questionable ones) • You're curious what actually separates people who enjoy their money from people who just have it • You believe there's more to financial success than just accumulating more Before You Hit Play, Think About This: What's one purchase you made that brought way more joy than its price tag would suggest—and can you figure out why? That's the kind of spending Morgan's talking about. Drop your answer in the comments—the basement wants to hear what actually brought you happiness. FULL SHOW NOTES: https://www.stackingbenjamins.com/the-art-of-spending-money-with-morgan-housel-1769/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

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