Stacking Benjamins: Your Gateway To Money And Personal Finance

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

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

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 deto

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 th

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 i

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 suc

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 e

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 favor

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

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

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

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-

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

How do you stand out in a competitive workplace—without shouting or burning out? In this episode, Joe and OG sit down with Lorraine K. 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

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 car

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

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

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?