Stacking Benjamins: Your Gateway To Money And Personal Finance

Is it time to break up with international stocks? They’ve been underperforming U.S. markets for years, so should we finally call it quits, or is there still hope for a global comeback? On today’s episode, Joe, OG, Paula Pant, and Jesse Cramer dig into the great international investing debate. Are international funds a lost cause? The panel unpacks why they’ve lagged U.S. stocks and whether diversification still makes sense. Beyond stocks: Exploring other asset classes—private equity, real estate, commodities, and collectibles (because who doesn’t want to invest in Beanie Babies and vintage lunchboxes?). The $3 coin mystery: Yep, that was a thing. And yes, it’s as weird as it sounds. Election results and wooden nickels: The intersection of money, history, and questionable currency choices. Weekend plans and podcast highlights: Because investing is important, but so is having fun. Of course, it wouldn’t be a Stacking Benjamins episode without some friendly debate, expert insights, and the occasiona

Ever experienced the gut-wrenching moment of losing a job—or worried about what you’d do if it happened? Today, we tackle how to prepare, what to do immediately, and the smartest moves to protect your finances if your job ever disappears. From building an emergency fund to making the most of employer benefits, we’ll walk you through the steps to keep your financial house in order when life throws a curveball. But that’s not all. Estate planning gets a shake-up thanks to the new Secure Act 2.0, and we’re diving into what it means for inherited Roth IRAs (hint: the government has new rules, and you’ll want to know them). And because we can’t resist a good detour, we also explore the real cost of horse ownership (spoiler: it’s more than just hay money) and why tide pooling is more financially educational than you’d think. All that, plus trivia, TikTok wisdom (or nonsense), and plenty of lively discussion from the basement crew. What’s Inside Today’s Episode: Job Loss Survival Guide: How to prepare before, dur

Feeling stuck in your financial plan—or maybe just in life in general? Whether it’s your money, career, or day-to-day habits, a little innovation can go a long way. Today, we’re breaking down how to rethink and restructure your approach to financial planning and work-life balance using lessons from Microsoft (yes, the Xbox folks). Dean Carignan and JoAnn Garbin insights on how to build a system for innovation—because the best financial plans (and lives) aren’t built by accident. Meanwhile, a woman was scammed out of her savings, and a major financial company had to pay a fine—even though they didn’t actually rip her off. What happened? And what does it mean for how we protect our own money? We’ll break it all down. Elsewhere in the episode, we discuss why trusted contact forms are crucial for safeguarding elderly relatives’ finances, how OG wants you to rethink your daily money habits, and why the Xbox case study holds lessons for designing a better financial plan. Plus, Doug has thoughts on podcast innovat

Love is in the air—and so are overpriced flowers, extravagant dinners, and some serious credit card regrets. In today’s episode, we tackle the financial pressure of Valentine’s Day and show you how to keep the romance alive without setting your wallet on fire. Joining us are financial pros Jesse Cramer, Sarah Catherine Gutierrez, and Len Penzo, who help us break down: The shocking reality of Valentine's Day spending – Who’s dropping the most cash, and is it really worth it? Avoiding post-holiday financial heartbreak – Strategies to celebrate without swiping yourself into debt. Creative alternatives to overpriced traditions – Ditch the $200 steak dinner and try these fun, budget-friendly ideas instead. The cost of love – From babysitting fees to restaurant markups, where is your money really going? Romantic gestures that don’t break the bank – Because a handwritten note might just score you more points than a last-minute gas station bouquet. The key to financial harmony in relationships – Talking m

Just when you thought Wall Street had run out of ways to package up risky investments and slap a shiny label on them—here we go again. Today, Joe and OG break down yet another overcomplicated, high-fee, and completely unnecessary financial product. Whether it’s preying on investor fears, promising market-proof returns, or just outright nonsense, we’ll help you spot the warning signs before you end up with a portfolio full of regret. But that’s not all. A viral TikTok tip about hiring your family members for tax benefits has been making the rounds, so we’ll dive into whether this is actually a genius tax strategy or just another case of the internet handing out half-baked financial advice. Plus, a listener asks about breaking into financial planning, and we lay out what it really takes—beyond the certifications and credentials (spoiler: sales skills matter). And Doug brings us a trivia question about one of the greatest art heists in history, proving that sometimes the best investment is knowing how to disappe

Swipe right on financial stability or get ghosted by your savings? While Joe's mom yells upstairs about who left the empty milk carton in the fridge (seriously, who does that?), we’re diving into the messy, complicated, and sometimes hilarious world of your relationship with money. Are you in a stable, long-term commitment with your finances, or are you stuck in a toxic on-again, off-again affair with impulse spending? Special guest Shannah Game, certified financial planner and author of Unraveling Your Relationship with Money, joins us to decode the emotional baggage we bring to our bank accounts. Meanwhile, Doug swears he’s figured out how to “game” the stock market using AI—spoiler alert: it involves a Magic 8-Ball. We also tackle some questionable dating preferences (because who doesn’t want to know if their financial habits make them swipeable?) and unpack the latest market shake-ups. In this episode:

Is automating your finances the key to effortless money management, or a one-way ticket to financial autopilot disaster? Paula Pant, Jesse Cramer, and Doc G join us to navigate the fine line between automation genius and accidental money mayhem. Done right, automation saves you time and stress. Done wrong? You might be funding a forgotten gym membership for the next five years.

What do scammers, fancy doors, and Twinkies have in common? Turns out, more than you think! Today, Joe, OG, and Doug take you on a wild ride through financial scams, fraud prevention, tax implications of dual residency, and... the surprising link between door quality and financial stability. (Yeah, we didn’t see that one coming either.) What’s Inside This Episode?

Retirement planning isn’t about waiting until 65—it’s about setting yourself up for a life you love starting right now! Today, Certified Financial Planner Benjamin Brant joins us to challenge traditional retirement thinking. What We Cover: ✅ Retirement planning starts now, not later – Why waiting to plan is the biggest mistake you can make. ✅ Dream big, but expect some ‘bad data’ – How testing financial plans (and life plans!) helps you refine your future. ✅ Why trust beats performance in financial planning – A new study shows that your advisor’s returns matter less than their integrity. ✅ The Monte Carlo simulation debate – What this financial tool actually tells you (and what it doesn’t). ✅ Childhood dreams, stand-up comedy, and time travel? – How revisiting past joys can shape a meaningful retirement. ✅ Choosing the right financial advisor – The #1 factor to look for before handing over your portfolio. Key Takeaways:

Ever dreamt of quitting your job early and sipping piña coladas on a beach? Before you tell your boss what to do with that job and start booking your one-way ticket to paradise, today’s roundtable might make you think twice. Join Jesse Cramer from The Best Interest, Paula Pant from Afford Anything, and our own OG as they break down the case against early retirement. The gang’s here to challenge the “quit work, retire early” dream and explore whether it’s really as awesome as it sounds—or if there are a few catches you haven’t considered. The conversation gets into the nitty-gritty of why early retirement might not be the smooth ride some people think it is. From the psychological toll of too much free time to the unexpected financial hurdles, our panelists share the real stories behind the headlines. What’s the balance between financial freedom and a fulfilling life? Can you really retire early without regret, or does the cost of quitting work too soon outweigh the benefits? And don’t forget about Doug’s wick

Ever wondered if you’re better off building your own target date fund instead of relying on a one-size-fits-all option? We’re diving into whether crafting your own investment mix is worth the effort, potentially saving you fees and giving you more control over your portfolio. But even the pros get it wrong sometimes—just ask Vanguard. We’re covering the major settlement they’re facing over misleading statements about taxes and target date funds, proving that even the big guys make costly mistakes. Meanwhile, a listener asks a great question about balancing tax optimization with financial flexibility—because what good is a perfectly tax-efficient plan if it ties your hands when you need cash? Plus, Doug takes us back to the origins of the gasoline-driven automobile, and there’s even an unexpected run-in with a Supreme Court justice (because why not?). And of course, we’ve got a TikTok moment that’ll have you questioning life choices and a few financial misconceptions that might just make you rethink your appro

What’s really standing between you and your financial goals? In today’s mentor, Jessica Moorhouse—financial counselor, podcast host, and author of Everything But Money—joins Joe to dive into the mental and emotional side of managing money. Jessica shares her journey with therapy, how relationships shape our financial habits, and the role of self-talk in creating a healthier money mindset. Whether you’re feeling stuck or just want a fresh perspective, this interview offers practical tools to help you take control of your financial future. In our headline segment, we explore the concept of a “no-buy” list—a clever strategy one woman used to pay off $34,000 in debt. Learn how gamifying financial goals can make saving more manageable—and even fun! Whether it’s cutting back on unnecessary spending or finding creative ways to save, this segment will inspire you to rethink how you approach your financial challenges. Here’s what we cover today: Saluting our troops—and wondering why Doug still doesn’t have a Navy Fe

Do financial boogeymen haunt your dreams? You’re not alone. Today, we’re diving into the worries that keep even the most seasoned finance nerds up at night. From concerns about index fund concentration to the fear of market manipulation and obsession with asset allocation, this episode tackles it all with insight and a healthy dose of perspective. Joining Joe and OG in the basement is an all-star panel: Paula Pant from Afford Anything, Jesse Cramer from Best Interest, and Dr. Jordan Grumet from Earn and Invest. Together, they’ll share strategies to conquer financial fears by staying calm, focusing on the big picture, and sticking to sound investment principles. And don’t miss the kickoff of the year-long Stacking Benjamins Trivia Challenge! It’s packed with brain-busting questions, lively debates, and, yes, the occasional cat butt reference (because it’s still the basement, after all). What’s Inside Today’s Episode: Meet the Contributors: Paula, Jesse, and Dr. Grumet join the crew. Index Fund Concentra

Feeling like the stock market is a high-stakes game of pinball lately? Not sure how to steady your hand when it comes to retirement accounts? In this episode, we tackle the rollercoaster of market volatility with actionable strategies to keep your retirement plans on track. Learn how to create an Investment Policy Statement, whether a Roth IRA still deserves a spot in your portfolio, and smart ways to withdraw from retirement funds without triggering costly mistakes. Plus, discover why trying to time the market is like predicting the weather with a Magic 8-Ball. Doug shares a tale involving a Chinese couple and some financial advice that’s worth sticking around for. Whether you’re building financial independence or refining your retirement strategy, this episode has you covered. What We Cover Today: Market Rollercoaster Madness: Stock, Bitcoin, and why patience pays off. Creating an Investment Policy Statement: Stay calm and strategy on. Listener Q&A: Chris from Georgia asks about retirement withdrawal

Feeling overwhelmed by debt or unsure how to navigate the fast-paced world of financial advice online? We’ve got you covered! This episode features Debt Relief Advocate Natalia Brown from National Debt Relief, who shares practical tips to climb out of financial trouble and steer clear of predatory practices. But that’s not all—we dive into the Wild West of TikTok crypto advice, where nearly 70% of content is misleading enough to derail your financial plans. Joe and OG break it all down with their trademark insight, helping you sort fact from fiction in the world of digital finance. Here’s what you’ll learn: Tackling Debt: Natalia Brown’s strategies for overcoming financial stress and avoiding common traps. Crypto Caution: Why TikTok might not be the best place for your financial advice (and what to watch out for). Credit vs. Stability: The difference between obsessing over credit scores and focusing on long-term financial health. Digital Disclaimers: How transparency (or lack thereof) online can impac

Ready to ring in the new year with a twist? On this episode of Stacking Benjamins, we consult the one and only Magic 8-Ball to make our bold predictions for 2025. Will the stock market be riding high, or is it headed for a tumble? What’s next for Bitcoin, and can Taylor Swift’s love life predict the future? Join Joe, OG, Len Penzo, and Mindy Jensen as they tap into the 8-Ball’s mystical power (or maybe just have a laugh trying) to forecast the year ahead. But before we get too caught up in the crystal ball, we take a look back at last year’s predictions. The 8-Ball hit some big marks, like predicting Nvidia’s rise, but it also missed a few. Along the way, Mindy shares her early (and hilarious) experience with Berkshire Hathaway, sparking a fun conversation about investing wisdom. And of course, Len brings his signature humor, diving into everything from crypto to drones to the wild world of Taylor Swift fandom. If you’re in the mood for financial insights, pop culture predictions, and a whole lot of fun, this

Can you save too much? Spoiler alert: absolutely. On today’s episode, Joe, OG, and Neighbor Doug tackle a financial pitfall many Stackers don’t think about—oversaving. Yes, socking away cash for the future is important, but at what cost? People often work extra hours, miss family dinners, skip vacations, and end up with regret instead of memories. The real tragedy? You can’t deposit lost time back into your bank account. We’ll share stories of people who saved so much they missed out on the life they were saving for, and we’ll dive into strategies to strike a better balance. From stress-testing your financial plan to understanding your personal inflation rate, we’ve got the tools to help you live for today and plan for tomorrow. And of course, we’ve got Doug’s trivia, a TikTok minute that might make you laugh out loud, and plenty of basement banter to keep things light. What’s Inside This Episode Opening: Joe, OG, and Doug kick things off with a mix of jokes, announcements, and OG’s latest attempt to seem c

Feeling like life’s demands have you tied up in knots while your financial future seems like a moving target? Time to take charge! Today in the basement, Anthony O'Neill pulls up a chair and shows you how to claim the head seat at your own table. He breaks down the power of having a personal vision, making intentional decisions that align with your goals, and being a stellar steward of your time and opportunities. But that’s not all—we’re looking ahead with some of the biggest names in tech. What do Bill Gates, Sam Altman, and other visionaries think 2025 will bring? (Spoiler alert: AI isn’t just for sci-fi anymore.) We’ll chat about how these changes will impact your work life and share some practical steps to stay ahead. And because life isn’t just about finances, the crew wraps things up with their latest binge-worthy TV and movie picks. It’s time to stack your entertainment queue as high as your Benjamins. What’s Inside This Episode

Feeling a little queasy about your financial plans for 2025? Fear not! Today, Joe steps out of the cozy basement and straight into the bustling chaos of Manhattan to bring you top-tier advice from some of the brightest financial minds. Joined by Paula Pant from Afford Anything, Nick Magiulli, author of the Of Dollars and Data blog, and Doc G from the Earn & Invest Podcast, this powerhouse panel digs into the money missteps you’ll want to dodge in the year ahead. From tackling FOMO in investments to learning why small, consistent changes are your financial BFFs, this episode is packed with practical tips to help you make 2025 a year of smart money moves (and fewer facepalms). What’s Inside: Meet our stellar guests and hear how New York City inspired their financial insights. Discover why chasing the next big investment trend could leave you behind. Learn how an investment policy statement can keep your goals on track. Avoid analysis paralysis when market uncertainty strikes. Uncover strategies to navigat

Does finding purpose in life feel overwhelming? What if you didn’t need a “grand” purpose to find meaning? Today, Dr. Jordan Grumet (AKA Doc G) joins us to explore the concept of “little P” purpose—those smaller, everyday moments that bring joy and fulfillment. From Julia Child’s journey to surprising stories of purpose in unexpected places, this episode will inspire you to find meaning right where you are. Here’s what we cover: Little P Purpose: How focusing on smaller, intentional acts can enrich your life. Purpose vs. Meaning: The difference, why it matters, and how it impacts your happiness. Doc G’s Journey: His personal insights on combating purpose anxiety and finding fulfillment. Julia Child and Beyond: Inspiring stories of people who embraced purpose at any stage of life. In headlines, we dive into 2025’s new tax brackets and savings limits—because a purposeful life is even better with a solid financial foundation. And don’t miss Doug’s trivia and some hilarious (and heartwarming) gift stori