The Stacking Benjamins Show

What do zipper injuries, holiday party mishaps, and servant leadership have in common? They’re all part of today’s wide-ranging look at careers—what to do, what not to do, and how to make your next move smarter (and safer). Joe Saul-Sehy, OG, and Neighbor Doug are joined by contributors Sandy Smith, Jesse Cramer, and a few classic career stories from the SB vault. Together, they explore: The surprising power of likability in the workplace How consistency and personal branding can open big doors Why some leadership styles flop and others inspire The real-life career missteps that made us all a little wiser A closer look at the Elevate Conference, which champions financial literacy for Black women And of course, it wouldn’t be a basement episode without a trivia challenge. This time, Doug delivers a stat that’ll make every listener squirm—let’s just say it involves zippers and emergency rooms. Whether you're climbing the corporate ladder, considering a leap, or just trying to avoid HR’s bad side, this episode packs in real advice and memorable stories from people who’ve been there, done that, and got the awkward email to prove it. Smart moves, cautionary tales, and Doug’s very specific warning about pants—this one's got it all. FULL SHOW NOTES: https://www.stackingbenjamins.com/improve-your-career-trajectory-1674/ 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 do you stand out in a competitive workplace—without shouting or burning out? In this episode, Joe and OG sit down with Lorraine Lee, a sought-after keynote speaker and former LinkedIn and Prezi leader, to dig into the real strategies behind building a career brand that lasts. Lorraine shares what she’s learned from coaching thousands of professionals, plus her own journey from behind-the-scenes to center stage. She introduces her EPIC framework—a smart approach that helps you craft a standout career identity built on: Experiences Personality Identity Community You’ll also learn: How to advocate for yourself without being “that person” The power of thoughtful feedback (and how to actually get it) Tactical tips to master Zoom meetings, digital presence, and virtual impressions Why embracing your differences can give you a serious edge in your career And after the career conversation? We shift into Stacker-style financial clarity—covering key money decisions people face during uncertain times: Should you wait to buy a home, or pull the trigger now? What do tariffs mean for your next car purchase? How should you approach investing when the market’s wobbling? From personal branding to practical budgeting, this episode gives you the tools to think clearly, act strategically, and build a future you’re proud of—no matter the economy. This one’s packed with high-leverage insights. Bring a notepad. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today’s episode blends career strategy with financial know-how, because who says you can’t build your personal brand and your balance sheet at the same time? Joe Saul-Sehy and OG explore what it really means to shape your professional reputation—from the way you show up in meetings to how you set (and measure) your career goals. Whether you're climbing the ladder, shifting industries, or mentoring others, this episode delivers practical ways to take control of how you're seen and what you stand for at work. Inside this conversation: The “RAVE” model for boosting your brand Why being a cheerleader for your colleagues makes you a standout How appearances and visibility (yes, even your Zoom background) impact your path Real-world tips for growing your influence without bragging—or burning out We also get into the intersection of tech and money: Is AI ready to replace financial advisors? (Short answer: not quite.) What metrics every financially literate person should understand And why your credit card points strategy might need a second look Plus, Doug breaks out a trivia challenge involving coin collecting, and we unravel the very weird truth behind the 1 cent piece. Whether you’re building a career, managing your money, or trying to do both with a little more polish—this episode’s packed with insights that stick. FULL SHOW NOTES: https://www.stackingbenjamins.com/your-career-brand-sb1672 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

Some people master reinvention. They move from one stage of life to the next with confidence, purpose, and an eye on long-term success. What if your financial plan could do the same? In today’s roundtable, Joe is joined by Alyssa Maes, Roger Whitney (The Retirement Answer Man), and OG to talk about what it takes to build wealth that lasts—not just through one season of life, but through all of them. 🎯 Inside the episode: What starting strong in your 20s and 30s really looks like How to fight lifestyle creep and sharpen your personal brand mid-career Why simplifying cash flow in retirement can be a game-changer The power of habits, automation, and adaptability across all stages And what consistent, thoughtful choices can do for your long-term success The thread running through it all? Knowing who you are, where you're going—and letting your financial decisions reflect that. We also sneak in a bit of trivia involving the most expensive comic book ever sold and a certain pop icon with a track record of breaking records (you can probably guess who). This episode is about more than music or money—it’s about making every era of your life count. 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 Taylor Swift teaches us about strategy, long-term thinking, and building an empire. Taylor Swift isn’t just a pop icon—she’s a master strategist. And in this episode, we unpack exactly how she built a cultural and financial empire with smart moves that offer powerful lessons for any Stacker. Joe Saul-Sehy sits down with Kevin Evers of Harvard Business Review Press to explore: How Taylor’s early partnerships set her on a path most artists never get to walk Why a clear vision—and the discipline to stick to it—can be a superpower How she turned frustration into creative fuel and conflict into leverage The surprising role MySpace and radio tours played in her initial success And what her story teaches us about marketing, risk-taking, and ownership But the show doesn’t stop there. Joe and OG also dive into: Grant Cardone’s 401(k) comments and whether his hot takes hold up The risks and rewards of real estate What crypto storage, insurance, and documentation mean for your financial safety net Plus, Mom’s neighbor Doug jumps in with a tax-themed trivia challenge—and a few surprising family stories to bring it all back home. Whether you’re a Swiftie, a strategist, or someone just trying to make smarter money moves, this episode delivers sharp takeaways and fresh perspectives. FULL SHOW NOTES: https://stackingbenjamins.com/all-about-taylor-swift-business-genius-1671 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

It’s Taylor Swift week in the basement, and we’re kicking things off by looking at the business behind the beats. Joe, OG, and the gang pull back the curtain on the intentional, savvy moves that took Taylor from breakout teen artist to industry powerhouse—and why her playbook might just work for your financial life, too. We’re talking about more than album drops. This episode covers: The power of controlling your own creative output Why strategic collaborations and timing matter How to avoid your own “sophomore slump”—in music or investing The underrated value of clarity, consistency, and small-but-steady improvements Then, we take a sharp turn toward the world of Roth IRAs, answering a listener question about the five-year rule and clearing up common misconceptions. If you’ve ever been confused by tax rules or unsure when you can touch your money, this one’s for you. Plus, there’s plenty more along the way: A local company stops making yardsticks (and we may be way too interested in that) Salutes to the troops, and a shoutout to basement podcasters A colonoscopy story you didn’t ask for, but will absolutely remember Whether you’re a Swiftie, an investor, or just here for the financial clarity, this episode brings strategy, insight, and unexpected takeaways you can actually use. FULL SHOW NOTES: https://stackingbenjamins.com/the-strategic-genius-of-taylor-swift-1669 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

Feeling anxious about where your money’s going? You’re not alone—and you’re not without a plan. In today’s episode, Joe is joined by OG, Mom’s neighbor Doug, and two sharp minds from the personal finance world: Paula Pant from Afford Anything and Dr. Jordan Grumet from Earn and Invest. Together, they take a deep dive into the many faces of investment risk, from the obvious to the overlooked. Because when it comes to your financial future, the real danger isn’t just volatility—it’s misunderstanding the terrain. Whether you're dipping a toe into international markets, piling into real estate, or wondering if your long-term plan can survive a little inflation, this episode will help you better understand the risks that matter—and avoid the ones that don’t. 💡 What’s inside: Why market risk feels scary—but often isn’t the real danger How liquidity and time horizon risks can quietly erode your strategy The danger of overconcentration (ahem, putting all your eggs in one ETF) What inflation, reinvestment, and credit risk mean for your future How to navigate longevity and foreign investment risks without flinching And of course, the basement wouldn’t be the basement without a few detours—including a surprise milkshake debate and Doug’s trivia segment that takes a sharp left into apple peels, Johnny Appleseed, and questionable coalition logic. If you’re ready to face the real dangers of investing—and stop fearing the ones that don’t deserve your attention—this episode’s got you covered. 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

Market volatility, overthinking portfolios, and why simple might be smarter. Trade wars. Tariffs. Tumbling markets. When headlines scream and your portfolio wobbles, what’s a Stacker to do? Today, we tackle how to invest confidently during uncertain times—without overcomplicating your strategy or losing sleep. We start by breaking down smart ways to manage volatility, whether you’re just getting started or already a seasoned investor. Then we dig into a great question from Stacker Ryan: should you stick with a diversified portfolio or choose a one-stop fund solution like those from Dimensional or Avantis? 🧠 In this episode: How to hedge against market swings without panicking Why keeping it simple could beat fancy fund strategies What most investors get wrong about stock market “danger” The power of a long-term mindset and how it pays off Tips for building confidence in your own investment decisions We also take a break for the TikTok Minute (yes, we found another gem), and Doug brings a trivia challenge that'll take you back to the dawn of the space race. And later, we open the mailbag: A listener asks how to plan solo for retirement ...and also wonders how much is too much for an emergency fund It’s a full basement session—investing insights, listener Q&A, and a few unexpected left turns. FULL SHOW NOTES: https://stackingbenjamins.com/talking-about-taxes-and-tariffs-in-your-investment-plan-1667 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

Tariffs got you sweating? We’ve got the strategy (and the LaCroix) to help you chill. Markets are wobbling, headlines are screaming, and you’re wondering if your portfolio is about to implode. Take a deep breath—and head down to the basement. In this episode, Joe Saul-Sehy, OG, and Mom’s neighbor Doug tackle the turbulence triggered by recent tariff changes. While others panic, we’re pouring the coffee and walking you through how to think smarter (and sleep better) during uncertain times. 🔍 Inside the episode: What recent tariff changes actually mean for your money How to protect your investments when markets get shaky Why doing nothing might be the smartest move The behavioral traps investors fall into—and how to avoid them Reassurance, real talk, and your weekly dose of Doug Whether you’re tempted to sell it all or just want a little peace of mind, this episode gives you tools to stay cool, stay invested, and stay the course. Because in the basement, we don’t panic—we plan. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Entrepreneurship, financial anxiety, and a guinea pig (yes, really). When you’ve got a stuffed guinea pig on your desk and a mic in front of you, it’s only a matter of time before you talk about that one time you ate guinea pig in Peru. (Spoiler: It was pretty good.) That’s how we open today’s show—but from there, things get real. Today’s main event features Rudy Mawer, founder of 60 Day Hustle, who joins Joe Saul-Sehy to share his incredible story. Rudy grew up in a modest home in England, raised by two world-class triathletes who pushed him to pursue excellence. He didn’t come from wealth—but he did build it, and fast. Rudy opens up about: His path from sports scientist to serial entrepreneur The role mentorship and strategic networking played in his success Why legacy matters just as much as hustle His latest documentary project and what drives him today Then, we turn to a conversation sparked by actor Seth Rogen’s recent interview with Dax Shepard. Rogen confessed he’s spent years saving out of fear—and maybe missed out on life in the process. So we ask: Are you hoarding cash out of anxiety? What happens when your savings plan becomes a cage? And how can Stackers find balance between security and spontaneity? Finally, we wrap up with one heck of a weather report. Mom’s neighbor Doug recounts the epic ice storm that left him snowed in, powered down, and questioning all his life choices. (Okay, maybe not all of them—but definitely his chainsaw strategy.) As always, Doug brings the trivia heat (and a little airline history), and we share some listener reflections that tie it all together. It’s a jam-packed episode—from financial fear to frozen driveways—with a little Peruvian culinary adventure tossed in. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-get-moving-on-your-money-goals-rudy-mawer-1666 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 good debt a myth? Should we all chase FIRE? The basement panel weighs in. In today’s Financial Concepts Friday roundtable, Joe brings the basement crew together for a lively “In or Out” debate on some of the most polarizing personal finance topics out there. Are we in or out on the idea of “good debt”? Do budgets really matter when you’re just starting out? Should you talk about money with your friends and family… or is that still taboo? Joining Joe are three financial thinkers who aren’t afraid to stir the pot: Paula Pant from Afford Anything Jesse Cramer from The Personal Finance for Long Term Investors Show OG from our own basement think tank (and planning headquarters) Together, they dig into: Whether any debt can actually be considered good If living without a budget is a fast track to financial regret—or freedom The upside (and awkwardness) of open money conversations How FIRE goals like retiring by 35 sound… and feel, once you really unpack them Plus, Mom’s neighbor Doug drops by with a trivia challenge that’ll have you laughing (and maybe yelling at your speaker). And of course, we wrap up with reflections that’ll leave you both entertained and a little bit wiser. So grab a LaCroix from the mini fridge and join us in the basement—this one’s packed with laughs, insights, and hot takes on cold, hard cash. FULL SHOW NOTES: https://stackingbenjamins.com/personal-finance-most-controversial-questions-1665 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 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

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

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

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

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

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

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

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

Ever feel guilty about that $7 airport coffee or the mystery fees that somehow turn your $15 DoorDash order into a $40 financial regret? You’re not alone. This episode, Joe Saul-Sehy is joined by Paula Pant (Afford Anything) and Justin Peters (The Struggle Is Real) to unravel the sneaky ways convenience drains our wallets. In this episode: Airport Food: The Ultimate Financial Heist – Why does a sad turkey sandwich cost more than a steak dinner? We investigate. Concert Tickets & Junk Fees – You found $50 tickets… but somehow the total is now $127? Yep, we’ve been there. The True Cost of Convenience – From Uber Eats to express shipping, when is paying extra worth it—and when are we just being lazy? Trivia Time: Pie Day Special! – Who knew McDonald's pie sales could spark heated debate? Well, now we all do. Wedding Costs Gone Wild – Creative ways to cut costs without making your guests eat ramen. The Ben Franklin Effect & Social Hacks – Want better connections without breaking the bank? Turns out, old Ben had some wisdom on that, too. All this, plus some hilarious personal finance confessions that will make you feel better about your last impulse buy. 🎧 Tune in, laugh, and learn how to keep more of your Benjamins! FULL SHOW NOTES: https://stackingbenjamins.com/places-we-know-were-overpaying-1656 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