The Stacking Benjamins Show

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...

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’s Inside T...

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? 🕵️‍♂️ Scams, Scams Everywhere! –...

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...

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 th...

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 mislead...

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...

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...

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 wa...

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...

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...

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 bac...

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 a...

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 pa...

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 wher...

What if you could spend guilt-free on what you love and keep your finances on track? In this episode, we’re joined by Jen and Jill from the Frugal Friends podcast to break down how to live frugally without crossing the line into being cheap. Frugal living isn’t about deprivation—it’s about prioritizing your spending on what truly lights you up while cutting back on the things that don’t. Jen and J...

What’s the secret to growing your income? In part two of our conversation with business dynamo Alex Hormozi , we explore the mindset shifts, skill-building tactics, and high-impact strategies that can take your earning potential to the next level. Whether you’re an entrepreneur or climbing the corporate ladder, this episode is packed with actionable insights to help you crush your 2025 financial g...

What would you do with $100 million a year? Today, we unpack Joe’s insightful conversation with business mogul Alex Hormozi , who breaks down the steps to massively increasing your income. Spoiler alert: It’s not about clipping coupons—it’s about thinking bigger, stacking the right skills, and taking strategic risks. Whether you’re an entrepreneur or rocking it in a 9-to-5, Alex shares: How to ide...

How do you go from a struggling actor to the top of the real estate world? Rounding out our greatest hits week of epic shows, we time travel back to when Ryan Serhant, star of Million Dollar Listing New York and the new Netflix series Owning Manhattan , shared his journey from rock bottom to building a billion-dollar real estate empire. In this episode, Ryan reveals how juggling multiple prioritie...

What’s the secret to turning small, consistent actions into million-dollar results? Legendary financial educator Paul Merriman joins the basement crew to share his powerful principles for building wealth, including the critical role of diversification and the magic of target date funds. Whether you’re just starting or refining your portfolio, Paul’s advice is packed with actionable strategies to h...

For this next installment to this edition of our Greatest Hits Week, we throw it back to a conversation Joe had with Zoe Chance about how to make influence your superpower. Do you ever feel like you just don’t have much influence over others? Not in a negative way, but in a way where you wish people would truly hear you. Sometimes we just need to take a step back and re-evaluate what we are trying...

How can kindness and a little math transform not just a company but an entire outlook on life? In this episode, we’re joined by James Rhee , who shares his remarkable journey from venture capitalist to CEO of a company dedicated to inclusivity and empowerment for plus-size Black women. James opens up about the values instilled by his Korean immigrant parents, the challenges of reviving a strugglin...

What happens when Doug gets visited by three ghosts in the basement? A classic holiday story gets a Stacking Benjamins twist in this special episode. Inspired by A Christmas Carol , we explore lessons from the past, present, and future to help you make smarter money moves. From learning to avoid past financial missteps to balancing life’s experiences with your financial goals, this episode blends...

The holiday season is here, and while it’s a time for celebration, it can also throw a curveball at your health and financial goals. In this episode, we’re joined by Angelo Poli from MetPro , who shares his no-nonsense approach to managing holiday indulgences without sacrificing all the progress you’ve made. Think of it as building a resilient portfolio—you can enjoy the party but still limit the...

As 2024 winds down, we’re taking a look back at the year that was—its challenges, its surprises, and the financial lessons we’ve all had to learn (sometimes the hard way). Whether you’re strategizing for big goals in 2025, making sense of unpredictable markets, or just trying to stay one step ahead of inflation, this episode has you covered. We’ve assembled a powerhouse panel of financial thinkers...