The Stacking Benjamins Show

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

What if the most important part of your retirement plan had nothing to do with your 401(k), IRA, or stock portfolio? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by filmmakers Pete Davis and Rebecca Davis, creators of the thought-provoking documentary Join or Die. They explore how community connection, not cash, may be the ultimate retirement strategy. Drawing inspiration from the late political scientist Robert Putnam (Bowling Alone), the Davises reveal why joining groups—book clubs, church choirs, rec leagues, neighborhood associations—might be more essential to your long-term well-being than your asset allocation. Together with Joe and OG, they unpack the data behind social decline, the healing power of showing up, and what the film Join or Die teaches us about leading a richer life beyond the numbers. Of course, Mom's Neighbor Doug pops in with trivia that proves he belongs (at least to this show). Whether you're on the path to retirement or simply looking for deeper purpose, this episode will make you think differently about how you stack your most valuable resource: time. Why joining a club may be just as critical to retirement as saving for it What Join or Die reveals about America's shrinking social networks How loneliness affects physical and financial health—and how to fight it Why your “portfolio of community” might be the highest-yield investment you ever make Ways to build meaningful connections now—even if you don't feel like a “joiner” Pete and Rebecca Davis share behind-the-scenes stories from making Join or Die Joe and OG reflect on what gives life meaning after the 9-to-5 ends Surprising data on the link between social capital and financial confidence Doug delivers a trivia challenge about famous clubs (and less-famous neighbors)

You can't plan a great retirement if you haven't first planned what you're retiring to. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug open up Retirement Week in the basement with a Monday that's equal parts insight, weekend recap, and questionable vehicle decisions.

Markets crashing? Interest rates spiking? Inflation roaring? Welcome to history. This week, we dig into 130 years of stock market meltdowns—from the panic of World War I to the Great Depression, 1970s stagflation, the dot-com collapse, and the 2008 financial crisis—to uncover timeless lessons that can fortify your financial future. Joe Saul-Sehy is joined by Miranda Marquit, Jesse Cramer, and OG to examine how investors have historically responded to chaos... and how you should, too. You'll learn why diversification matters, why panic rarely pays, and why staying the course (even when it's scary) can be the smartest move of all. Of course, this wouldn't be the Stacking Benjamins Show without a trivia detour that involves mailing children through the U.S. Postal Service (yes, that happened). Buckle up for laughter, insight, and financial takeaways that are as practical as they are entertaining. What WWI, the Great Depression, and 1970s inflation can teach us about investing Why “The Lost Decade” wasn't a loss for long-term thinkers How to build a resilient portfolio that weathers the storm Our infamous trivia game: How much could a kid weigh and still be legally mailed in the 1920s? A few money-saving hacks, podcast updates, and your weekend preview from the basement Whether you're a seasoned investor or just building your financial foundation, this episode will leave you smarter, more confident, and—let's be honest—way more amused than the average market history lecture. FULL SHOW NOTES: https://stackingbenjamins.com/lessons-from-stock-market-history-1695 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 happens when you mix financial strategy with a healthy dose of cultural commentary? You get Rich Girl Nation. This week on The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Katie Gatti Tassin, the powerhouse behind Money with Katie and author of the new book Rich Girl Nation. Together, they unravel the sneaky ways consumerism shows up in our lives—from pricey trends to status-signaling spending—and how it messes with our wallets. Katie dives into the “hot girl hamster wheel” of overspending, the wage gap, and why negotiating your salary (without flinching) is one of the best financial moves you can make. She also offers sharp, tactical advice on job-hopping for higher pay and automating your money to avoid lifestyle creep. Meanwhile, the crew throws in real-life stories, from Cybertruck depreciation to celebrating financial independence in more ways than one. And of course, Doug drops in with a trivia twist that keeps things weird—because it wouldn't be the basement without a little curveball.

Is your wallet feeling lighter... but your closet's full of regret? Joe, OG, and Mom's neighbor Doug are throwing open the basement door to tackle one of the trickiest parts of personal finance: consumerism. Whether you're a recovering impulse buyer or knee-deep in buy-now-pay-later regrets, this episode's got your back—and maybe your budget.

Can building wealth be as entertaining as a round of trivia in the basement? We think so—and today's episode proves it. Joe Saul-Sehy is joined by Doc G, Paula Pant, and Jesse Cramer to play a fast-paced financial game show based on 11 expert-approved ways to grow your wealth. From boosting your income and dialing in your budget to the eternal tug-of-war between paying down debt and investing more, this episode delivers wisdom with a side of basement-brand chaos. But we don't stop at just the basics. Our roundtable dives into: How homeownership plays into your wealth picture (even if it's not as sexy as index funds), Why insurance coverage might be your best wealth-preserving move, The truth about improving your credit score without obsessing over every point. Plus, a trivia celebration of 50 Cent's Vitamin Water payday turns into a lesson in surprise wins—and surprise losses. Whether you're just beginning your wealth-building journey or refining your strategy, this episode brings practical insights, hearty laughs, and a gentle nudge to rethink what really grows your net worth. How to increase your income (without selling essential organs) Budgeting strategies that actually stick Why investing early matters—and when paying off debt takes priority The real ROI of proper insurance coverage A homebuying debate that might ruffle some financial feathers Birthday trivia for 50 Cent and the Vitamin Water deal that made him a legend End-of-episode takeaways you'll want to write down (or tattoo, if that's your thing) Stackers, whether you're navigating rainy days or planning for a brighter financial future, today's conversation will help you stack smarter, live better, and maybe even walk away with a new strategy—or at least a smile. FULL SHOW NOTES: https://stackingbenjamins.com/our-favorite-ways-to-grow-wealth-1692 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

After Monday's primer on why your portfolio needs some international flavor, we're following up with a deeper dive—this time with someone who lives and breathes global markets. Joe Saul-Sehy and OG welcome Joy Yang, Head of Index Product Management at MarketVector Indexes, to talk through how to actually invest beyond U.S. borders. Joy explains how ETFs can help investors capture international growth while minimizing risk—and why country-specific and sector-specific ETFs might just be your new best friend. You'll also hear insights on investing in private markets, the rise of digital assets, and whether private equity in your 401k is a brilliant idea… or a cautionary tale. But don't worry, the basement stays weird. Doug brings the trivia heat with a Martha Stewart–Eliot Spitzer stumper, and the episode wraps with some creative audience feedback (including one Stackers' AI-powered school project that caught our attention). Topics Covered: How to diversify globally without overcomplicating your portfolio The power of ETFs for targeting specific markets and sectors What you really need to know before considering private equity in retirement accounts Balancing simplicity with opportunity in a world of shiny investment options The limits of “going big or going home” when it comes to risk and return Stackers, if you're looking for smart ways to expand your portfolio's reach—or just curious what index creators think about Bitcoin—this episode delivers insights, laughs, and a grounded reminder: simple can still be smart. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-invest-globally-with-joy-yang-1691 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 global is your portfolio, really? This week in the basement, Joe Saul-Sehy, OG, and the gang zoom out from the U.S. markets and take us on a whirlwind trip around the investing world. Spoiler alert: the case for international investing is stronger than you think—and it's not just about chasing higher returns. It's about risk reduction, smart diversification, and maybe even admitting that the U.S. isn't always the world's MVP. You'll hear how developed and emerging markets fit into a well-balanced portfolio, how correlation works in your favor (yes, this time that's a good thing), and what history tells us about going global. Joe and OG share practical advice for how to get started, when to rebalance, and how much international exposure might make sense for the average Stacker. Then in the second half, we pivot from markets to money buffers: listener Jeff from Cleveland wonders how to set insurance deductibles based on the state of his emergency fund. We break down how to think about the real return on your rainy-day stash—because spoiler: it's not about the interest rate, it's about your resilience. To wrap things up, we share timeless wisdom from Stackers across the country on what they'd tell new graduates about money, life, and how not to blow that first paycheck on a jet ski. Why international investing may improve both your returns and your risk profile How much of your portfolio to allocate internationally—and what history suggests What "correlation" really means and why it's your friend (at least in investing) Risks and common misconceptions of investing overseas How to choose between developed vs. emerging markets Portfolio tools to visualize your asset mix and expected outcomes Why your emergency fund's best ROI might be peace of mind How to align insurance deductibles with your liquidity cushion What our community of Stackers wishes they had known after graduation FULL SHOW NOTES: https://stackingbenjamins.com/making-the-case-for-international-investing-1690 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

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:

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:

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:

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.

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

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).

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. FULL SHOW NOTES: https://stackingbenjamins.com/renting-vs-buying-forever-1677 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.

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.

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?

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.

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.

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.

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.

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.

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.

Choosing the Best Tax Software for Your Needs Tax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you're a side hustler, crypto investor, or just looking for a free filing solution. Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by which software stands out this year. H&R Block's virtual tax prep – If you want real humans to double-check your numbers, this might be your go-to. Which tax software works best for unique situations – Side gigs, stock trading, crypto investments… different situations call for different solutions. Navigating Tax Day without the stress – Tips to avoid last-minute panic and make sure you're not leaving money on the table. Crypto scams and meme coins – Because tax season isn't stressful enough without adding that mess into the mix. Meanwhile, Doug serves up world-famous trivia with a nod to classic children's books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, and—of course—movie recommendations. If tax season feels overwhelming, this episode breaks it down, keeps it light, and helps you pick the right software to file with confidence. 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 if working for yourself could be the game-changer your finances need? Grant Sabatier thinks so, and today, he's diving into the realities of entrepreneurship—from smart strategies to potential pitfalls. Where to start if you're considering entrepreneurship – Not every side hustle is a winner, so how do you know if this path is right for you? The power of systems and constraints – Why guardrails and structure matter more than unlimited freedom. Pricing strategies and finding customers – Because even the best ideas need paying customers. Entrepreneurial misconceptions – Spoiler: It's not all Ferraris and private jets. Can your wedding be a tax deduction? – We explore the entertaining but highly questionable ways some people try to make this work. Meanwhile, Doug serves up trivia on the highest-grossing console game ever (bet you won't guess it). And if you stick around long enough, let's just say there may or may not be a discussion about a comedy movie that turns financial struggles into pure entertainment. But, you know… no promises. If you've been toying with the idea of starting your own thing, this episode is packed with insights, real talk, and a few surprises along the way. FULL SHOW NOTES: https://stackingbenjamins.com/unlock-your-inner-entrepreneur-with-grant-sabatier-1654 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 the pressure to constantly tweak your investments? Today, we uncover the surprising benefits of financial inaction with insights from CFP Dana Anspach, Len Penzo, and OG. We dive into the wisdom of sometimes doing nothing—because, as it turns out, sitting on your hands (financially speaking) can be a power move. Why lazy portfolio management might be the smartest strategy you'll ever adopt (spoiler: it involves less work). The power of downtime—turns out, stepping away from your money might actually make you richer. Why your future self will thank you for setting up auto-pay (hint: fewer late fees, more naps). The sneaky ways peer pressure messes with your finances—and how to keep the Joneses from running your budget. When rebalancing your portfolio is necessary…and when it's just a fancy way to micromanage yourself. A wildly unexpected insurance claim (because finances are never boring in the basement). Oh, and Doug's got a trivia question about a particularly controversial activity that was banned—because, apparently, not everything fun is legal. Stick around for weekend plans, final thoughts, and maybe even a surprise or two (because we like to keep you on your toes). This episode originally aired on June 10, 2022. Please disregard any mention of current events. The original show notes can be found here. 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

A great financial plan isn't just about numbers—it's about creating a roadmap that turns dreams into reality. Today, Joe and OG take a trip down memory lane, reflecting on their favorite parts of building a great financial plan. Whether you're tackling long-term goals, fine-tuning your tax strategy, or simplifying complex decisions, they'll walk you through the key elements that turn financial chaos into a well-oiled machine. Breaking down big goals into bite-sized wins – Because climbing a financial mountain is easier when you focus on one step at a time. The magic of tax strategies – Why a little planning now can keep more Benjamins in your pocket later. Risk management done right – Avoiding financial pitfalls so your plan stays strong, no matter what life throws your way. The power of simple solutions – Complexity doesn't always mean better. Sometimes, the best financial strategies are the easiest to execute. The role of a financial guide – Whether you DIY your plan or bring in an expert, knowing when to get guidance is a game-changer. Meanwhile, Doug tackles a ‘Winnie the Pooh'-inspired predicament (honey jars may or may not be involved) and drops some surprising trivia on the massive market value of antidepressant drugs. If you're ready to streamline your financial life and celebrate your progress along the way, this episode is packed with insights, strategy, and a few unexpected twists. This episode originally aired on January 18, 2023. Please disregard any mention of current events. The original show notes can be found here. 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 felt overwhelmed by buying a car or managing your time? You're not alone. Today, we tackle both topics with expert insights and a few unexpected surprises along the way. Car buying decoded – Joe sits down with Phil Reed, Senior Consumer Editor at Edmunds, to break down the best strategies for buying new or used cars, leasing vs. buying, and negotiating with dealers like a pro. The ultimate time management playbook – Paula Pant, Dominique Brown, and returning guest Carrie Smith share real-world productivity hacks—whether you're self-employed, working 9-to-5, or just trying to make better use of your day. Avoiding social media missteps at work – The team dives into the do's and don'ts of posting while employed. Email overload? Phone calls running your life? – Smart strategies to take control of your inbox and stop wasting time on endless calls. Celebrity wealth secrets and entertainment picks – Because financial wisdom can come from surprising places. A roadside hawk encounter?! – An unexpected story that proves you never know what's coming next. With practical advice, engaging discussions, and a few twists you won't see coming, this episode packs in everything you need to take control of your finances and your time—without taking life too seriously. Learn more about your ad choices. Visit podcastchoices.com/adchoices

If disaster struck tomorrow, would your financial essentials be ready to grab and go? Today, Joe—along with contributors Paula Pant from Afford Anything, Jesse Cramer from Personal Finance for Long-Term Investors, and our resident expert OG—assemble the ultimate financial go bag. Meanwhile, Doug handles his usual duties as announcer, trivia master, and general chaos instigator. The must-have documents – Passports, Social Security cards, insurance policies... what belongs in your bag, and what can stay in the filing cabinet? Cash vs. digital access – How much should you keep in physical cash? And is gold really a smart emergency asset, or just a really heavy way to slow yourself down? Estate planning and emergency preparedness – The financial moves today that can make a crisis less stressful later. Password managers: genius or a liability? – We debate whether your digital keys should be stored in the cloud, on paper, or tattooed in invisible ink. Trivia showdown: Doug tests the team's knowledge with a question that (probably) has nothing to do with financial preparedness. Campus co-op stores and Harvard history—why are we talking about this? You'll find out. If you've been meaning to get your financial house in order for emergencies, this episode has everything you need to build your own financial go bag—without overpacking. FULL SHOW NOTES: https://stackingbenjamins.com/your-financial-go-bag-1650 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 insurance setup rock-solid, or are you unknowingly leaving gaps that could cost you big time? Today, we break down the essentials of managing risk in our no-nonsense (but totally entertaining) insurance guide. How much coverage do you really need? We tackle the must-haves and the unnecessary add-ons that might just be draining your wallet. Auto, home, life, and disability insurance—what's essential and what's overkill? We walk through the key policies that keep you protected without breaking the bank. Oddball insurance policies—are they worth it? From pet insurance to that ‘just in case' coverage you saw on late-night TV, we separate the smart buys from the money traps. A TikTok minute that perfectly sums up the difference between dogs and cats. Trust us, you'll relate. Listener questions: Breaking up with a financial advisor—when it's time to walk away and how to do it right. Insurance company showdown: Who's the biggest player in the game, and does size really matter? DIY money moves: How to take over your own investment accounts without making costly mistakes. Stackers, this episode is packed with tips, laughs, and real-world insights to help you protect what matters—without wasting a dime. Don't miss 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