The Stacking Benjamins Show

Is your grocery bill beefier than your sandwich? This week, Joe Saul-Sehy, OG, and Neighbor Doug unpack inflation in a way that only we can—by biting into Len Penzo’s Annual Sandwich Survey. Yes, prices are up, and yes, you can still eat well without triggering a credit card crisis. But it’s not just meat and mustard on today’s menu. We’re also serving a fresh look at 401(k) “leakage”—that drip-drip-drip of hardship withdrawals that's turning your retirement plan into a leaky faucet. You’ll get pro-level insight on how to patch those holes before your future income soaks the floor. And if you’re paying for (or dreading paying for) college, Christine from the Stacker community, who works in higher ed, joins to offer sharp and timely advice on keeping costs in check—from completing the FAFSA to finding overlooked aid. Len Penzo’s Sandwich Index Which sandwiches give you the most delicious bang for your inflation-adjusted buck? (Spoiler: bologna stages a quiet comeback.) 401(k) Trouble Brewing Hardship withdrawals are on the rise. Why it matters, how to avoid them, and what better options exist when life throws you a cash crisis. Tracking Expenses Like a Pro Joe, OG, and Doug explore the subtle ways inflation seeps into your budget—and how paying attention to where your money leaks gives you power back. Higher Ed, Lower Bills Stacker Christine breaks down must-know tips on navigating skyrocketing tuition, including a FAFSA pep talk that could save you thousands. Tuna vs. Roast Beef: The Sandwich Showdown Plus: Is the BLT still king? Can the humble tuna salad hold its ground against the mighty Big Mac? And where does salami fit into the sandwich power rankings? Trivia, Movie Talk, and Park City Tales No Stacking Benjamins episode is complete without a detour or three—from Doug’s trivia trap to stories from the road and screen. Takeaway for Stackers: In high-cost times, it’s the small wins—like swapping in store brands, packing a lunch, or tracking that budget leak—that give you the edge. And while it’s tempting to ignore those tiny cracks in your retirement plan or daily spending, you’re much better off fixing them before the flood. Want to brag about your favorite money-saving sandwich? Drop into the Basement Facebook group and share it—bonus points if it doesn’t involve bologna. FULL SHOW NOTES: https://stackingbenjamins.com/len-penzo-2025-annual-sandwich-survey-1717 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

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 personal finance: What do you do when a windfall lands in your lap? Whether it's an inheritance, work bonus, or prize money (maybe you finally won that game show you keep applying to), the panel explores what smart, emotionally grounded, and goal-aligned decisions look like in the face of sudden cash. Start With the Why Before you touch a dime, the crew walks through the importance of mindset, goals, and not falling into the “I deserve it” trap that has sunk many a lucky winner. Debt vs. Invest vs. Enjoy High-interest debt? Retirement accounts? Travel dreams? The panel weighs each strategy—and surprises us with their personal priorities. Behavioral Finance & Windfall Psychology Why do people tend to mismanage unexpected money? From mental accounting to lifestyle creep, learn the hidden traps and how to sidestep them. The 401(k) Match Dilemma Is it better to max out tax-advantaged accounts or build an emergency fund? The team hashes out smart order-of-operations for stacking your windfall right. Trivia Break: St. Paddy’s Parade Edition Neighbor Doug makes sure you don’t learn too much without a little distraction. Can you guess when the first St. Patrick’s Day parade was held? How They’d Spend It Ever wonder what Joe, OG, Paula, or Jesse would do with an extra 50 grand? From practical moves to guilty pleasures, we get a peek into each of their financial brains. Don’t let windfalls drift into “found money” syndrome—align with your long-term goals first. Paying off high-interest debt = guaranteed return. But balance it with your future-focused investments. Emotional awareness is just as crucial as spreadsheets when a windfall hits. Take a beat before making decisions. Give yourself permission to enjoy some of the money—just make sure it’s intentional, not impulsive. Got a windfall story or dream scenario? Tell us how you’d handle an extra $50K in our Basement Facebook group. Let’s see who would invest it, who would renovate the kitchen, and who would finally launch that mobile alpaca petting zoo. FULL SHOW NOTES: https://stackikngbenjamins.com/how-to-treat-a-financial-inheritance-1716 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

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 conversation that makes math feel less like a chore and more like a cheat code for life. Dintersmith, best known for his education advocacy and the acclaimed documentary Most Likely to Succeed, joins us fresh off the release of his latest book, Aftermath—a compelling look at how we rethink learning in a world that’s evolving faster than ever. With over a decade visiting 500+ schools and a deep passion for practical math, Ted shares how skills like estimation, probability, and prediction can help you make smarter decisions—especially when it comes to your money. Why Prediction Beats Perfection Ted explains why being roughly right about your spending, investing, and life planning is more powerful than being precisely wrong. Consumer Math is the Real MVP From family budgets to grocery store run-throughs, Dintersmith makes a case for math that actually applies to your everyday decisions—and shows how parents and educators can teach it at home. A Fourth-Grade Science Test Gone Wrong An unforgettable story about how one exam nearly crushed a curious kid’s confidence… and what it says about how we measure learning. The Financial Advisor Dilemma Solved Joe Saul-Sehy and OG unpack the key differences between bank advisors and independents, including fee structures, fiduciary responsibilities, and what really matters when choosing your financial guide. Lights, Camera, Reform Dintersmith shares the powerful stories behind his documentaries—including Most Likely to Succeed and the upcoming Multiple Choice—and why his new book Aftermath is a must-read for anyone who believes education should prepare us for real life. The Psychology of Math Anxiety and Money Mistakes We explore how bad math experiences lead to financial decision paralysis, and how to rebuild confidence one calculation at a time. Neighbor Doug’s Trivia Takes the Stage Whether it connects to math or not, Neighbor Doug delivers his signature trivia moment with flair—and possibly a tangent or two. Math shouldn’t be a barrier to better money decisions. This episode arms you with a fresh mindset for yourself, your kids, and maybe even your school board. If you’re a math teacher, financial coach, or just someone who once cried over fractions, we want to hear from you. Join the conversation in our Facebook group, The Basement, and tell us: How are you making math practical—or how do you wish you’d learned it? FULL SHOW NOTES: https://stackingbenjamins.com/math-that-you-need-in-your-life-1715 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

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 the new rules like a pro. Here’s what we unpack: The 2025 Tax Overhaul: What changed, what stayed the same, and how it affects your bottom line Credits vs. Deductions: Why that $1 credit might be worth more than a $5 deduction (math, but fun) Above-the-Line Moves: Claim valuable deductions without itemizing New Wins for Givers and Drivers: Above-the-line charitable contributions AND (drumroll…) personal auto loan interest is back! Family Tax Breaks: Expanded dependent care accounts and beefed-up child credits 50 and Thriving: New 401(k) catch-up rules that can help you max out your retirement Listener Mailbag: JJ asks how to contribute more to his 401(k) after age 50—and we bring the strategies The TikTok Minute: Because money wisdom can live on the internet too Doug’s Trivia & Financial Shenanigans™: Of course You’ll walk away with clear, practical takeaways that could add thousands to your bottom line—without needing to read the tax code (you're welcome). FULL SHOW NOTES: https://stackingbenjamins.com/upcoming-tax-changes-1714 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

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 Anything) Jesse Cramer (Personal Finance for Long-Term Investors) Together, they unpack the emotional, practical, and strategic side of planning your next chapter—whether you're closing in on retirement or still working toward it. The biggest fears about retirement: from running out of money to running out of meaning. The “one more year” syndrome: why it's so tempting to delay and how to break through. Time freedom vs. financial freedom: how to align your life goals with your money strategy. Tactics to conquer fear: income layering, diversified portfolios, annuities, and rental properties. Psychology matters: why no spreadsheet ever solved a midlife identity crisis. Real stories from the panel: wins, struggles, and lessons from guiding others through retirement transitions. Planning for healthcare and long-term care: because your body didn’t get the early retirement memo. Plus, the usual basement mayhem: trivia, playful host banter, and a few unexpected laughs (we won’t call them “funny”—you know the rule). Mark’s Money Mind podcast Afford Anything podcast Personal Finance for Long-Term Investors AARP: Retirement Readiness & Addressing Fear Blog post: “Fear Will Hold You Prisoner. A Diversified Portfolio Will Set You Free.” Retire to something, not just from something. Purpose beats spreadsheets. Understand your income plan. Know where the money will come from, rain or shine. Plan for healthcare now, not later. Medicare, long-term care, and medical surprises deserve your attention. Don’t go it alone. The best plans are ones you understand, but it helps to get advice from trusted sources. Whether you’re on the cusp of calling it quits or still deep in the grind, this episode will help you prepare—not just financially, but mentally and emotionally—for a retirement you’ll love. FULL SHOW NOTES: https://stackingbenjamins.com/what-is-holding-you-back-from-reaching-your-goals-1713 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 🎧 Dive deeper, grab resources, and check out past episodes at StackingBenjamins.com Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 (Jordan Grumet) are joined by Nick Maggiulli, Chief Operating Officer at Ritholtz Wealth Management and author of Of Dollars and Data, to talk about lessons from his new book: The Wealth Ladder. Nick breaks down the six wealth levels, from scraping together your first emergency fund to navigating the complexities of generational wealth. They explore: Why increasing your income early on trumps frugality (sorry, coupon clippers). What “wealth plateaus” really look like, and how to recognize when your strategy needs to evolve. The hidden trap of goal obsession, featuring a cameo from world #1 golfer Scottie Scheffler. The true cost of career choices, and why opportunity cost might be the silent killer of long-term growth. Why content and code are two of the most powerful wealth-building levers available (especially when they scale without needing a lunch break). Whether you're stuck in Level 1 or fantasizing about Level 6, this episode has practical, perspective-shifting advice on building wealth—and more importantly, how to enjoy the process without losing your sense of purpose along the way. Stackers don’t just want to make money—they want to master it without letting it become their master. This conversation bridges income, investing, identity, and intention in a way that gives you both clarity and confidence. You might even stop worrying about skipping that $5 latte… or realize it’s time to start coding that app you keep talking about at parties. FULL SHOW NOTES: https://stackingbenjamins.com/invest-differently-and-move-faster-1712 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

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 wealth ladder—from humble beginnings at $10K all the way to $10 million—and explain how your financial priorities, risks, and strategies evolve as your net worth grows. How to avoid mismatched advice: Why taking financial tips meant for someone in a different stage can set you back instead of move you forward. Net worth brackets and behavior shifts: What you should be thinking about at $10K, $100K, $1 million, and beyond—and what not to worry about yet. When Roth IRA conversions make sense—and when they really don’t: With new legislation impacting retirement tax planning, Joe and OG break down the implications with help from Robert Powell of The Street. Diversification, risk, and behavioral pitfalls: What the pros get wrong and how to stay grounded no matter how big your stack grows. Community-driven insights: From listener milestones to new Stacking Benjamins swag sightings, you’ll hear how Stackers are winning in their own lives. As always, the team weaves in laughter, sarcasm, and that unmistakable basement charm—complete with Doug’s new mug, a calendar confusion history lesson, and a household disaster caused by what can only be described as “revenge rain.” A Robin Williams–themed trivia segment to warm your heart (and test your memory) Batty Betty’s wild TikTok take on relationship finance Practical investing and estate planning ideas that don’t make your eyes glaze over Why You’ll Love This Episode:If you’re trying to level up without falling prey to the one-size-fits-all advice machine, this episode delivers a realistic blueprint. It’s equal parts roadmap and reminder: where you are right now matters more than where someone else thinks you should be. Stacker takeaway? Clarity beats comparison. Especially when it comes to money. FULL SHOW NOTES: https://stackingbenjamins.com/build-your-wealth-ladder-1711 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

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 conversation on building meaningful goals and avoiding common life derailers. He’s joined by two all-star minds in money and behavior: Paula Pant from Afford Anything, who reminds us that "you can afford anything—but not everything," and Jordan Grumet from Earn & Invest, who offers the life-and-death perspective (literally—he’s a hospice doctor) on why we need to act now, not later. Together with OG and Doug, the roundtable unpacks six common ways people unknowingly waste their lives, including: Being "busy" instead of effective Letting fear of failure hijack your plans Overthinking every move Paralysis from too many choices Constant hustle with no progress Indecision dressed up as careful planning You’ll hear hard-earned lessons, subtle mindset shifts, and tips for creating financial and personal momentum. Plus: The surprising link between indecision and regret, backed by Dr. Ellen Langer’s research Smart strategies for eliminating distractions and taking better action The difference between motion and movement—especially when it comes to your goals and your money And, of course, we sprinkle in some classic basement banter, a rowdy trivia throwdown, and Joe’s favorite kind of weekend preview (the kind where no one actually follows their own advice). Why this episode is worth your time: Whether you’re staring down your 2025 goals or still recovering from a rough Q1, this is your shot of clarity. No judgment—just real talk from people who’ve been there, made the spreadsheet, and occasionally lit it on fire. 🎯 You’ll walk away with: A clearer idea of what’s holding you back Practical ways to structure smarter financial goals Permission to stop doing all the things and start doing the right things Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 a side hustle, or just trying to stay on track past February, Gary shares a field-tested, civilian-approved approach to achieving your biggest financial and personal milestones. From defining SMART goals to building sustainable habits and multiple income streams, this conversation is all about real results—no fluff, no buzzwords. But that’s just the first mission. In the second half, Joe and OG dive into one of retirement’s trickiest topics: long-term care insurance. Is it worth it? When should you buy it? How do you know if it’s right for your situation? Consider this your tactical briefing before walking into a battle you didn’t know you were fighting. You’ll also hear: Why borrowing someone else’s goals is a recipe for burnout. The power of structure and accountability (no drill sergeant required). What “Trump Accounts” are and why you might want to know about them. How to evaluate long-term care coverage before it sneaks up on your plan. Joe’s high-speed review of the new Formula One movie (spoiler: he’s not drafting behind the popcorn). Packed with tactical advice, unexpected laughs, and practical strategies, this episode delivers a full-stack toolkit for Adventurers looking to thrive—financially and personally—in the second half of 2025 and beyond. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 tolerance, or just trying to remember where you wrote down your resolutions, this is your nudge to hit the financial reset button—with style. From Alex Hormozi’s take on embracing risk and skill-building to JL Collins' wisdom on why buying happiness with money is a flawed formula, this episode pulls powerful insights from our brightest guests so far. We revisit career advice from media powerhouse Bonnie Hammer, dig into intentional spending habits, and reflect on the subtle connection between mindset and long-term success. Oh—and don’t miss a moment of Joe and OG’s always-wise, occasionally-weird banter as they break down topics like: Why goal setting isn’t just for January—and how to mid-course correct before December sneaks up on you. Risk management in real life (not the textbook version). Why mindful consumption isn’t about cutting back, but tuning in. What makes retirement joyful beyond the spreadsheets. How your community can be the most underrated part of your portfolio. If you’ve felt a little off-course—or just want a chance to recalibrate without the guilt trip—this episode delivers practical steps and encouraging reminders to help you make the second half of 2025 your strongest yet. Got goals? Let’s reset ‘em. And if not, we’ve got a few ideas for those, too. FULL SHOW NOTES: https://stackingbenjamins.com/our-review-of-first-half-2025-1708 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

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

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

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

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

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

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 be possible—if you’ve got the right mix of investments, a solid plan, and a bit of courage. But we don’t stop there. Because with greater freedom comes greater risk (especially if you're leading with vibes instead of strategy). The guys tackle the sequence of returns risk that can derail early retirement years, and how to build a portfolio that helps you sleep at night—even during a market storm. Meanwhile, Doug drops in with an unexpected (and very British) culinary experience, Joe fields a listener question comparing financial plans to workout routines (is your Roth IRA doing enough reps?), and yes... we revisit our fan-favorite segment on how food waste is wrecking your budget. Why the 4% rule might be too conservative (or maybe just outdated). What diversified portfolios and asset class strategy have to do with a longer-lasting nest egg. How to prepare for market downturns before they happen—and what to do if you're already in one. Why retirement joy isn’t just about spreadsheets—it’s about the psychology of spending with confidence. Which type of green tea is the superior kind (depending on which side of the TikTok aisle you're on). How to reduce food waste and put that extra savings toward your bigger financial goals. If you’re approaching retirement—or even just dreaming about it—understanding how much you can safely spend without sabotaging your future is the question. This episode combines historical insight with today’s market realities to give you the real math and mindset you need to retire well…and maybe even with a smile. FULL SHOW NOTES: https://stackingbenjamins.com/problems-with-the-4-percent-rule-1702 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

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 financial “gurus.” The conversation is rooted in a provocative blog post by Christine Luken that calls out four common money mantras—and the team dives into each one with classic basement wit, spirited debate, and hard-earned wisdom. Topics on the table: Do you really need a budget, or can you thrive without one? Are rigid financial formulas helpful or harmful? Is willpower the key to financial success—or just a scapegoat? Does cutting up credit cards actually solve your spending problems? Along the way, you'll hear banana jokes (yes, multiple), a heated trivia contest about obsolete technology (looking at you, LaserDisc), and some good-natured trash talk that might just surprise you with how insightful it gets. This episode is packed with nuance, laughs, and practical takeaways for Stackers who are tired of the one-size-fits-all guru approach. Whether you’re team budget or team spreadsheet freestyle, there’s something here for you—plus a solid reminder that when it comes to personal finance, the best advice is the advice that fits your life. FULL SHOW NOTES: https://stackingbenjamins.com/lies-damn-lies-and-statistics-1701 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

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 (hello, aging parents!), this episode is full of relatable scenarios and actionable strategies. Stackers Torin, VJ, Lori, and Michelle ask everything from: How much is too much in your emergency fund? What happens to inherited IRAs when you're already juggling financial priorities? What should single people be doing right now to prepare for the future? How do you juggle helping aging parents while keeping your own goals on track? Plus, we mix in commentary from Kevin at Edward Jones and longtime listener Ron—offering insights from inside the financial services world and the Stacker community. The guys debate personal finance media narratives, give practical advice for budgeting large windfalls, and reflect on why saving feels easier in theory than in practice. Also covered in this episode: Why financial advice often skips over single individuals—and what to do about it Emergency fund strategies: where to park the money, how much to keep, and how to make peace with the fact it isn’t earning sky-high returns How to prioritize debt, student loans, savings, and investing without setting off a financial anxiety spiral The value of short-term tradeoffs when you’ve got long-term goals All delivered with the basement’s signature charm—where the coffee is lukewarm, the guidance is practical, and the jokes… well, let’s just say they’re dividend-eligible. This episode is a perfect listen for: New Stackers building their financial foundation DIYers trying to juggle competing money goals Anyone who’s inherited assets and doesn’t want to mess it up People who’ve realized adulting is basically managing 14 financial priorities at once and still remembering to bring snacks. FULL SHOW NOTES: https://stackingbenjamins.com/answering-your-questions-mailbag-1700 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

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 your work, your privacy, and your future, this episode is a must-listen. They kick off with a surprising headline: Gen Z workers are sidestepping AI entirely—not by resisting it, but by choosing careers where machines can’t compete (like landscaping and trades), and using AI tools to grow their businesses faster. This sparks a full-on basement debate about how technology has historically impacted jobs, what the next evolution might look like, and whether AI will make our lives easier… or just busier. In today’s show: Why some jobs may disappear—but others are about to explode with opportunity The surprising role AI is playing in blue-collar and skilled trade growth Why being AI-curious (not AI-phobic) is your best financial move New tech tools that supercharge productivity—from transcription wallets to note-taking bots How AI is already transforming education and career paths What to do right now to stay ahead of the AI curve Then the guys shift gears to a more sinister topic: data privacy. CNET recently reported which free AI chatbots are scooping up the most of your personal info—and which are surprisingly respectful. The gang reveals which apps are best to trust, and which are like letting Zuck crash on your couch (bad idea). We’ll also hear from listener John, who wants to hire a financial advisor but isn’t sure where to start. Joe and OG break down how to find the right fit, why fees aren’t the most important factor, and the one question that tells you if someone’s worth hiring. Plus: Doug’s trivia on egomaniacal coin designers A TikTok minute about U2, dating apps, and dad jokes Back porch chatter about Pontiac Azteks, water treatment careers, and IMAX concert pilgrimages Takeaway: AI isn’t just a tech trend—it’s reshaping our economy, our careers, and even how we learn. Whether you’re a Gen Z worker, mid-career professional, or planning your retirement, now’s the time to lean in, explore what AI can (and can’t) do, and secure your future before the bots beat you to it. FULL SHOW NOTES: https://stackingbenjamins.com/ais-coming-for-your-job-how-to-outwit-the-robots-1699 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

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 already deep into your golden years, you'll hear candid, practical insights from three financial thought leaders who specialize in making your money last. Joining Joe are Dana Anspach, retirement planning expert and founder of Sensible Money, Karsten Jeske (aka “Big ERN” from Early Retirement Now), and Frank Vasquez, aka Uncle Frank, host of Risk Parity Radio. Together, they bring decades of academic research, professional experience, and plain old common sense to questions like: What’s the real safe withdrawal rate—and why does it depend on more than just spreadsheets? Should you chase simplicity or embrace complexity in managing retirement funds? What role do annuities and guaranteed income play in reducing late-life anxiety? How do you plan for cognitive decline without spiraling into existential dread? What’s the difference between spending confidently... and spending carelessly? You’ll also hear why lumpy expenses, long-term care surprises, and behavioral quirks can trip up even the best-laid plans—and how to bulletproof your strategy now. And yes, we get nerdy. Risk parity, sequence of return risk, and portfolio glidepaths all make guest appearances—but always with your favorite Stacking Benjamins charm and plain-English style. Because retirement doesn’t need to be scary... but it does need to be intentional. Why your investment approach needs to evolve once paychecks stop The strengths and blind spots of the “4% rule” How emotions (not just inflation) affect safe withdrawal strategies When it makes sense to annuitize, and when it absolutely doesn’t How to adjust for cognitive decline in your financial plan (and still maintain autonomy) The “spend conservatively early” myth—debunked Tips for managing healthcare and other unpredictable late-life costs Whether you’re a retiree, a pre-retiree, or a spreadsheet-loving financial independence buff, this deep-dive episode will give you the confidence to manage the second half of your financial life like a pro. This isn't just about stretching your dollars—it's about building a life worth spending them on. So grab your planner, pour a cup of whatever says “retirement-ready” to you, and let’s get smarter (and maybe just a bit weirder) about your golden years. FULL SHOW NOTES: https://stackingbenjamins.com/create-your-retirement-spending-plan-1698 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