The Stacking Benjamins Show

This week, we’re getting deep (like, basement-deep) into what it means to flourish. Join Joe, OG, Paula Pant, and special guest Ryan Doolittle as they unpack a brand-new study on happiness. Spoiler: it’s not just about stacking cash. From the influence of childhood experiences to the surprising power of community, autonomy, and faith, this episode asks whether true wealth is more emotional than numerical. Plus, Ryan shares his adventures from his new series Try and Ryan—where he road-tests hobbies that might just add meaning to your retirement (and your Tuesdays). What we’re exploring in the basement: 🌱 What the latest research says about flourishing—and why it’s not just for the rich 👶 How childhood trauma or support plays into long-term happiness ⛪ Religious attendance: a surprising common thread in many “happy” lives 🎯 Autonomy, mastery, and purpose at work—and why they might matter more than promotions 🌍 Why Finland keeps winning the “World’s Happiest Country” race (and what Americans might learn from it) 💰 How financial flexibility might be more valuable than financial freedom 🧓 Gender and retirement happiness: why the experience might not be equal across the board 🛠️ Ryan’s “Try and Ryan” series and how picking up hobbies can boost life satisfaction 🏎️ Also: Trivia mayhem involving the Indy 500, Paula’s cat gets a shoutout, and OG still won’t drive stick 🎙️ Want to be wealthy and well? Tune in for a conversation that’s as heartfelt as it is hilarious—because in the basement, we believe money’s just the fuel. Flourishing is the journey. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Turns out, saving $3,000 a year might be easier (and tastier) than you think. This week, we’re dishing up big savings with Bryan Suddith, who turned his family’s runaway grocery bill into a budget-friendly game—complete with freezer hacks, local meat tips, and food waste strategies that actually work. He joins Joe, OG, and guest co-host Len Penzo (yes, that Len Penzo of LenPenzo.com fame) to share how mindful meal planning can make your wallet and your taste buds happy. We’re also talking about a Wall Street Journal piece that reveals why high schoolers are ditching traditional degrees for skilled trades... and landing $70K jobs right out of the gate. Plus, Doug helps us navigate one of life’s most awkward questions: What do you call your friend’s mom? (Hint: it’s not “Linda.”) What’s stacked inside this episode: 🧾 How Bryan gamified his grocery budget and saved thousands—with zero meal-prep burnout 🥩 Freezer hacks, locally sourced meats, and the joys of slow-thawed financial wins 🥦 Food mindfulness: the surprising connection between awareness and grocery savings 🎯 Why budgeting doesn't have to feel like punishment (especially when TikTok is involved) 🎙️ Bryan’s bonus storytelling and public speaking tips for anyone who has to talk to humans 🔧 Trade school is trending: why $70K jobs are showing up before diplomas 🧰 Should your teen consider HVAC over Harvard? We unpack the growing case for skilled trades 🤷‍♂️ Conan O'Brien, Doug, and the Great Parental Naming Debate of 2025 💡 If you’ve ever overpaid at the grocery store or underestimated a plumber’s paycheck... this one’s for you. Bring your shopping list and your sense of humor—we’ll meet you in the basement. 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

Think you're being lied to at work? You probably are. From boardrooms to bank accounts, this episode pulls no punches. We’re stacking double the wisdom on this special Memorial Day episode, as Joe Saul-Sehy interviews two powerhouse guests: Bonnie Hammer, former vice chair of NBCUniversal and bestselling author, and Dr. Erika Rasure from Beyond Finance. Whether it’s breaking glass ceilings or breaking out of debt, this episode is your roadmap to reclaiming control. Inside the episode: 💼 Bonnie Hammer calls B.S. on the “15 lies women are told at work” — and explains how to rewrite the rules 🎬 Behind-the-scenes of Suits and why even hit shows face wild career landmines 🧠 How your attitude and teamwork can make or break your climb to the top 💬 Dr. Erika Rasure on why 50% of Americans don’t trust themselves with money — and how to start 💸 The real emotional blockers behind budgeting, saving, and staying out of the online cart trap 🧍‍♀️ Gender and generational gaps: why confidence with money isn’t equally distributed (but should be) 🛠️ Financial “practice weeks” and mindset shifts to get unstuck from shame and paralysis ✅ A simple path to get control over your debt without feeling like you’ve failed Also: Doug delivers his own Memorial Day tribute and trivia, because of course he does. 🎙️ Ready to outsmart bad advice and start building on your own terms? This one’s for you — whether you’re climbing the corporate ladder or clawing your way out of credit card debt (or both). Learn more about your ad choices. Visit podcastchoices.com/adchoices

Memorial Day weekend is here, which means it’s officially time to break out the grill, the beach bag… and maybe that travel budget spreadsheet. But don’t worry—this isn’t a guide from travel influencers who hike barefoot with artisanal backpacks. Nope. This episode is brought to you by your favorite money geeks in Joe’s mom’s basement. Joe Saul-Sehy, OG, Jesse Cramer, Crystal Hammond, and Doug gather 'round the card table to share their best budget-friendly travel strategies, hilarious vacation stories, and maybe one or two travel fails. From choosing the right travel companion to navigating airports like a boss, this crew drops loads of practical wisdom for making your summer adventures awesome and affordable. You’ll learn why credit card points can be your best friend, how to pick lodging that won’t make you cry (or bankrupt you), and why packing a toothbrush is a good idea… even if Doug’s trivia makes you question the timing. This isn’t expert advice. These are the musings of people who spend more time optimizing their wallets than their luggage. And that’s exactly why you’ll leave feeling better prepared to tackle your own summer travel—without the jet-setter guilt trip. Kicking off summer with a Stacking Benjamins travel roundtable Real-life travel hacks from people who care more about budgeting than boarding groups Credit card point strategies that actually work Hot takes on hotels, Airbnbs, and airport snacks Why picking the right travel buddy can make or break your trip The one item Doug thinks was more important than nylon (it’s… something) Whether you’re headed to the lake, the mountains, or just your backyard with a cold drink, join the crew for a hilarious and practical celebration of summer travel. 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 cupcakes, frosting, and financial independence have in common? This week in the basement, Stacking Benjamins welcomes legendary personal finance thinker JL Collins, author of The Simple Path to Wealth, to connect the dots between simple investing and sweet, stress-free success. In a lively conversation with Joe Saul-Sehy, OG, and Mom’s neighbor Doug (who may or may not be launching a frosting-themed protest movement), JL shares timeless wisdom on avoiding complexity, embracing low-cost index investing, and why FU money is more than just a clever phrase—it’s freedom in a bank account. You’ll hear JL’s take on portfolio allocation, debt’s sneaky impact on your future, and how to survive volatile markets without sacrificing your peace of mind. If you’ve ever felt stuck in a soul-crushing job? JL’s got some perspective you’ll love. Then, in the second half of the episode, Joe and OG shift gears to answer a listener question from Mike. He’s wondering about the efficient frontier—yes, we’re getting fancy now—and wants to know how to move beyond the Simple Path. Joe walks through the different asset classes he thinks about when crafting a diversified portfolio, while OG shares how to think through asset allocation as your wealth and confidence grow. Whether you’re curious about real estate, international investing, or just how much to hold in bonds, you’ll walk away with a clearer picture of what your portfolio could look like after “graduating” from JL’s foundational advice. Why keeping it simple beats chasing trends What “FU money” really means—and how to get it The truth about withdrawal rates and why they matter When debt becomes a dream killer Tips for navigating market downturns without panic How to find freedom without spending a fortune JL’s surprisingly profound parable about a monk, a minister, and money Doug’s hot take on the great frosting vs. cake debate A deep dive into the efficient frontier and how to set up your asset allocation beyond VTSAX Joe Saul-Sehy and OG’s thoughts on portfolio construction for seasoned investors JL’s insights have inspired millions on the path to financial independence—and now it’s your turn. Tune in, take notes (or don’t, we’ll recap it in the 201), and remember: sometimes the sweetest success starts with doing less. 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 it summer already, or is that just our theme park budget melting in the sun? Either way, we’re kicking off the season with our annual guide to roller coasters, churros, and how not to hurl after one too many loops. Theme Park Insider’s Robert Niles returns to share the biggest news in amusement park land—from a new Disney park in Abu Dhabi (what?!) to Universal Orlando’s game-changing Epic Universe. But what’s a summer kickoff without a good ol’ whiplash reminder that your brain can’t be trusted when it comes to investing? Joe Saul-Sehy and OG dive into Jason Zweig’s latest insights about how our market “memory banks” mess with decision-making, and why 2008 probably wasn’t as scarring as your gut tells you. And yes, Doug's trivia ties it all together—with corn dogs, naturally. How to actually save money at theme parks without having to sleep in a costume closet. The surprising reason a $1,400 day at Disney might be your own fault. Which new coasters (and old favorites) are worth the detour this year. Why your gut—and your "market memory"—could be sabotaging your investments. The last time the stock market went down multiple years in a row (hint: not 2008). What Robert’s favorite underrated U.S. parks are (spoiler: Dollywood shows up, again). How to strategically splurge or save at the parks—merch fans, avert your eyes. 🎢 This one has thrills, chills, and the occasional spreadsheet. Just how we like it. 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 really moves the needle on your happiness—making more money or saving more of what you’ve got? This week, Joe Saul-Sehy and OG are joined by Paula Pant, Jesse Cramer, and the guy who still owes money on his Beanie Baby collection—Doug—for a roundtable filled with bold financial takes and even bolder choices. It’s a rapid-fire round of “either-or” dilemmas, and while nobody gets voted off the island, a few sacred cows are gently tipped over. Should you max out your retirement account or finally slay your student loans? Ditch credit cards for cash? Bet your future on crypto or keep it stuffed in a fireproof mattress? Our panel debates these decisions and shares real-life stories of what’s worked—and what’s blown up like a microwaved burrito. Of course, it wouldn’t be The Stacking Benjamins Show without a detour or two: we dig into financial hoarding (how many dusty envelopes is too many?), reveal why your credit score might be your best frenemy, and serve up some vintage airplane trivia, just to keep things classy. So whether you're team "Earn More" or team "Cut Back," this episode delivers the kind of guidance that helps you feel a little more confident making your next money move—even if it’s just saying no to another financial “shortcut.” Topics covered include: Why more income might not be the golden ticket The case for ditching your credit card (and why that makes Doug twitchy) Saving vs. investing vs. spending like you’re already retired What financial hoarding reveals about your mindset Index funds vs. individual stocks: which one should get your long-term commitment? The never-ending crypto debate (now with 12% more existential dread!) How obsessing over your credit score may or may not ruin your weekend If you’re figuring out how to balance today’s latte with tomorrow’s freedom—or you just want to feel smarter about money than your cousin Gary who “invests in vibes”—this one’s for you. And remember, no matter how much you earn or save, the real ROI is tuning in with the Stackers each week. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like money is a never-ending game of not enough? Today, we're rewiring that thinking. Our special guest, Leisa Peterson—author of The Mindful Millionaire and now The Money Catalyst—joins us to talk about abundance, scarcity, and how to stop living life like you're budgeting for armageddon. (Hint: It's okay to order the nice wine now.) Joe Saul-Sehy and OG also shine a light on the resurgence of alternative investments. Is it innovation... or just Wall Street’s way of sneaking in high fees through the back door? Plus, we roll into Doug’s trivia, a TikTok Minute that flips the script on a certain “draft pick,” and, of course, a few stories that prove—yet again—that golf is no game for the frugal. “Am I YOLO-ing or just broke?” Why framing matters more than frugality From scarcity to satisfaction: How one moment in Paris changed Leisa’s relationship with money You call that a tip? The surprisingly deep conversation behind street musicians, champagne, and generosity Alternative investments are back (again?) Why your advisor might pitch you on ditching the market... and why you should think twice Personal growth through fiction: Leisa's surprising journey from nonfiction burnout to a book that might just fix your wallet and your heart When the camel arrives with a skeleton on its back: Doug’s trivia gets weird (and somehow financial) TikTok Minute: What happens when a 50-year-old thinks he just got drafted into the NFL OG’s rule of thumb: Volatility isn’t the villain—it’s the entrance fee 🪄 PS: Boston-area Stackers! Joe’s coming your way May 20th. Get all the meetup deets at stackingbenjamins.com/meetup 🎧 Listen now and start living (and spending) like abundance is already yours. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do most millionaires have in common? No, it’s not a yacht named “Compound Interest.” It’s mindset. In this episode, Joe Saul-Sehy and OG kick off Mindset Week by welcoming Sam Dogen, the Financial Samurai himself, to help you start your journey toward a million-dollar net worth—one intentional step at a time. Sam shares why building wealth is less about luck and more about grit, clear goals, and a killer savings rate. He explains why $250,000 is the magic milestone where compounding takes over, why your “why” is more important than your budget, and how a simple house-to-car ratio can reveal whether you’re cruising toward financial freedom or stuck in the valet lane. You'll learn: Why your first $250,000 is the hardest (and most critical) How to find your “why” and let it drive your money decisions Why some people crush millionaire goals while others stall out The pros and cons of prioritizing student loan payoff How real estate, entrepreneurship, and mindset play a role in long-term success Plus, Doug delivers trivia about the world’s most millionaire-dense country (hint: it’s not the U.S.), and Joe announces a live event with Boldin’s Steve Chen to help you master retirement planning tools. All that and a wink toward OG’s dream car obsession (which definitely didn’t come from the after-show... wink wink). 💥 Want to level up your financial thinking? This episode is your launching pad. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-start-on-your-financial-journey-with-financial-samauri-sam-dogen-1681 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

If your grocery bill has you doing double-takes at the checkout line, you’re not alone—and this episode of The Stacking Benjamins Show is packed with practical ways to take control of your food spending. Joe Saul-Sehy is joined by Janice Torres of the Yo Quiero Dinero podcast, regular contributor OG, and the always-frugal Len Penzo to serve up real-world grocery hacks that help you stretch your dollars without skimping on flavor or quality. You’ll learn: How meal planning can shrink your bill (and your food waste) When buying in bulk pays off—and when it’s just a trap Why pre-packaged foods might be eating up your budget Which apps help you unlock store discounts and cash back And whether starting a garden is actually worth it for your bottom line We also dig into freezer strategies, the art of cutting back on meat without feeling deprived, and a few guilty pleasure restaurants that somehow always find their way back into our budgets. It’s a money-saving roundtable that’s equal parts helpful and hilarious. Come for the grocery hacks, stay for the side dishes of personality. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Your burning questions fuel this episode! Joe Saul-Sehy, OG, and special guest Christine Benz of Morningstar unpack some of the biggest questions facing investors today—especially those just starting out. We kick things off by diving deep into target date funds. They promise simplicity—but do they deliver long-term results? We explore when they work, when they don’t, and what you should consider if they’re part of your portfolio. Then Christine shares a graduation-season masterclass in financial advice: How to begin investing, even when you feel behind Why lifestyle creep is the silent killer of wealth The importance of building habits now that will serve you for decades Resources and reading recs that can actually move the needle for new grads (and not-so-new grads) We also answer listener questions on: Whether refinancing your mortgage is still a smart move How global shifts in labor and supply chains may impact your finances And why it’s time to give your favorite retirement calculator a second look And somewhere in all this… someone may or may not reveal a dream dinner scenario that involves a pair of country music legends. But, you know, that part probably didn’t happen. Probably. Whether you're just graduating, recalibrating, or rethinking your strategy entirely, this episode is your invitation to stack smarter—and have a little fun while you do it. 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

Joe Saul-Sehy sits down with bestselling author Jen Sincero, the powerhouse behind You Are a Badass and You Are a Badass at Making Money. If you've ever felt stuck in financial quicksand or caught in a loop of scarcity thinking, Jen brings the fire (and the funny) to help shift your mindset and start building wealth from the inside out. You’ll hear: How Jen went from living in a garage to becoming a seven-figure entrepreneur The mindset shifts that changed her relationship with money—and could change yours Why self-talk and affirmations aren't fluff—they're your financial launchpad Simple ways to start reprogramming how you think, spend, and save The importance of consistent investing—even when you’re not feeling confident We also touch on: Why your HSA might be a secret investing weapon What to know as tax deadlines approach (and how not to panic) A listener’s creative approach to investing—and how OG and Joe weigh in Plus: marathon filming, TV mishaps, and trivia surprises from Mom’s neighbor Doug If you're ready to stop playing small with your money and start stacking like a badass, this episode will give you the mindset—and motivation—to get going. FULL SHOW NOTES: https://stackingbenjamins.com/you-are-a-badass-at-making-money-greatest-hits-week-1678 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

Buying vs. renting: it’s one of the most emotionally charged—and financially misunderstood—topics in personal finance. This week on The Stacking Benjamins Show, Joe Saul-Sehy, OG, and guests Jesse Cramer and Chris Luger enter the ring to challenge the conventional wisdom behind homeownership. It’s not just a polite chat. It’s a full-on basement debate where no side goes unchallenged. You’ll hear: The surprising math behind renting—and why it’s not “throwing money away” What most homeowners don’t budget for (and pay dearly for later) Why buying a house might be one of the best—or worst—decisions you ever make How lifestyle, mobility, and flexibility factor into long-term wealth The emotional traps, practical benefits, and tough tradeoffs on both sides Plus, Mom’s neighbor Doug gets into full trivia-host mode with a Star Wars challenge, and we sprinkle in some good-natured jabs, marketing wisdom, and a reminder that there’s no one-size-fits-all answer. If you’ve ever bought a home, sold one, rented, or even thought about doing any of the above—this episode will make you think twice. 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

Retirement might be the goal, but the journey? Full of curveballs. On today’s episode, Joe Saul-Sehy is joined by special guest co-host Len Penzo of LenPenzo.com, along with OG and Neighbor Doug, for a no-holds-barred look at what really derails retirement plans—and how to build a strategy that can handle the chaos. From unexpected job loss to rising long-term care costs, adult kids moving back home, and even changing relationship dynamics, this episode dives into the often-overlooked risks that can chip away at your retirement dreams. Inside the episode: What to consider when evaluating long-term care insurance How job instability late in your career can throw off your timeline The growing trend of adult children impacting their parents’ retirement Grandparents becoming full-time caregivers—and the financial toll that brings Relationship shifts and widowhood in retirement Downsizing, austerity planning, and staying financially flexible Plus, our TikTok Minute features Gary V on why taking a step backward might be the smartest move forward. And as always, Doug brings the trivia heat—this time, with a nostalgic nod to a certain potato-headed toy. With Len Penzo in the basement, the insights (and squirrel references) are extra sharp. Prepare to laugh, learn, and rethink what “retirement ready” really means. FULL SHOW NOTES: https://stackingbenjamins.com/four-things-that-can-derail-your-retirement-plan-1676 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

When it comes to living your best financial life, good health isn't a nice-to-have—it’s a must-have. In today’s episode, we welcome Angelo Poli from MetPro, who shows us why smart fitness and nutrition choices are just as important as smart money moves. Drawing on insightful listener questions, Angelo shares: How consistent habits—not extreme diets—build the foundation for long-term health The real scoop on intermittent fasting, the carnivore diet, and other trending fads Practical ways to lower blood pressure, boost energy, and keep momentum even when life gets busy Why managing your wellness is one of the most powerful ways to protect your future earning potential and enhance your quality of life Because stacking Benjamins isn't just about saving—it's about having the health and energy to enjoy them. Later in the show, Joe and OG tackle smart financial strategies for uncertain markets: How to choose the right financial advisor when fear is everywhere What really matters in your long-term financial plan Why stability and experience will always outperform hype And finally, we dig into Home Equity Lines of Credit (HELOCs)—what they are, when to use one wisely, and how to avoid the common traps. This episode is all about stacking smarter—your wealth, your health, and your life. FULL SHOW NOTES: https://stackingbenjamins.com/improve-your-health-and-your-finances-in-2025 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 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