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!

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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!

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Buying vs. renting: it’s one of the most emotionally charged—and financially misunderstood—topics in personal finance. This week on The Stacking Benjamins Show, Joe Saul-Sehy, OG, and guests Jesse Cramer and Chris Luger enter the ring to challenge the conventional wisdom behind homeownership.

It’s not just a polite chat. It’s a full-on basement debate where no side goes unchallenged.

You’ll hear:

The surprising math behind renting—and why it’s not “throwing money away”

What most homeowners don’t budget for (and pay dearly for later)

Why buying a house might be one of the best—or worst—decisions you ever make

How lifestyle, mobility, and flexibility factor into long-term wealth

The emotional traps, practical benefits, and tough tradeoffs on both sides

Plus, Mom’s neighbor Doug gets into full trivia-host mode with a Star Wars challenge, and we sprinkle in some good-natured jabs, marketing wisdom, and a reminder that there’s no one-size-fits-all answer.

If you’ve ever bought a home, sold one, rented, or even thought about doing any of the above—this episode will make you think twice.

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!

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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!

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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:

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:

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!

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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:

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!

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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:

You’ll also learn:

And after the career conversation? We shift into Stacker-style financial clarity—covering key money decisions people face during uncertain times:

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.

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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:

We also get into the intersection of tech and money:

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!

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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.

The thread running through it all? Knowing who you are, where you're going—and letting your financial decisions reflect that.

We also sneak in a bit of trivia involving the most expensive comic book ever sold and a certain pop icon with a track record of breaking records (you can probably guess who).

This episode is about more than music or money—it’s about making every era of your life count.

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!

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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:

But the show doesn’t stop there. Joe and OG also dive into:

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!

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