The Stacking Benjamins Show

Latest Episodes:

How To Waste Your Life (or hopefully, not) SB1710 Jul 18, 2025

Show notes

Ever feel like you're working hard but getting nowhere? You're not alone—and you might be stuck in a productivity trap, not a purpose-driven plan. In this episode of The Stacking Benjamins Show, we tackle the big one: how to avoid wasting your life. (No pressure.)

Joe Saul-Sehy kicks things off with a tongue-in-cheek nod to all the ways we fritter away time—before pivoting into a power-packed conversation on building meaningful goals and avoiding common life derailers.

He’s joined by two all-star minds in money and behavior:

Paula Pant from Afford Anything, who reminds us that "you can afford anything—but not everything," and
Jordan Grumet from Earn & Invest, who offers the life-and-death perspective (literally—he’s a hospice doctor) on why we need to act now, not later.

Together with OG and Doug, the roundtable unpacks six common ways people unknowingly waste their lives, including:

Being "busy" instead of effective
Letting fear of failure hijack your plans
Overthinking every move
Paralysis from too many choices
Constant hustle with no progress
Indecision dressed up as careful planning

You’ll hear hard-earned lessons, subtle mindset shifts, and tips for creating financial and personal momentum. Plus:

The surprising link between indecision and regret, backed by Dr. Ellen Langer’s research
Smart strategies for eliminating distractions and taking better action
The difference between motion and movement—especially when it comes to your goals and your money

And, of course, we sprinkle in some classic basement banter, a rowdy trivia throwdown, and Joe’s favorite kind of weekend preview (the kind where no one actually follows their own advice).

Why this episode is worth your time:
Whether you’re staring down your 2025 goals or still recovering from a rough Q1, this is your shot of clarity. No judgment—just real talk from people who’ve been there, made the spreadsheet, and occasionally lit it on fire.

🎯 You’ll walk away with:

A clearer idea of what’s holding you back
Practical ways to structure smarter financial goals
Permission to stop doing all the things and start doing the right things

FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-waste-your-time-on-stupid-stuff-1710/

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Create Goals that Stick (with Ret. Lt. Cdr. Gary MacDermid) Jul 16, 2025

Show notes

Want to crush your goals and avoid getting crushed by long-term care costs? In today’s episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Retired Lieutenant Commander Gary McDermott, a former U.S. Navy officer turned business coach, who brings military-grade discipline to the world of goal-setting and financial success.

Whether you’re working toward a promotion, launching a side hustle, or just trying to stay on track past February, Gary shares a field-tested, civilian-approved approach to achieving your biggest financial and personal milestones. From defining SMART goals to building sustainable habits and multiple income streams, this conversation is all about real results—no fluff, no buzzwords.

But that’s just the first mission. In the second half, Joe and OG dive into one of retirement’s trickiest topics: long-term care insurance. Is it worth it? When should you buy it? How do you know if it’s right for your situation? Consider this your tactical briefing before walking into a battle you didn’t know you were fighting.

You’ll also hear:

Why borrowing someone else’s goals is a recipe for burnout.
The power of structure and accountability (no drill sergeant required).
What “Trump Accounts” are and why you might want to know about them.
How to evaluate long-term care coverage before it sneaks up on your plan.
Joe’s high-speed review of the new Formula One movie (spoiler: he’s not drafting behind the popcorn).

Packed with tactical advice, unexpected laughs, and practical strategies, this episode delivers a full-stack toolkit for Adventurers looking to thrive—financially and personally—in the second half of 2025 and beyond.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-set-and-achieve-your-goals-gary-macdermid-1709

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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Mid-Year Financial Reset: Key Takeaways from the First Half of 2025 (SB1708) Jul 14, 2025

Show notes

Still on track to crush your 2025 goals? Or has the year felt more like a Super Mario Kart banana peel moment?

In this special mid-year review episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG take a pause from the summer sprint to look back at the most impactful lessons, conversations, and themes from the first half of 2025. Whether you’re rethinking your budget, fine-tuning your risk tolerance, or just trying to remember where you wrote down your resolutions, this is your nudge to hit the financial reset button—with style.

From Alex Hormozi’s take on embracing risk and skill-building to JL Collins' wisdom on why buying happiness with money is a flawed formula, this episode pulls powerful insights from our brightest guests so far. We revisit career advice from media powerhouse Bonnie Hammer, dig into intentional spending habits, and reflect on the subtle connection between mindset and long-term success.

Oh—and don’t miss a moment of Joe and OG’s always-wise, occasionally-weird banter as they break down topics like:

Why goal setting isn’t just for January—and how to mid-course correct before December sneaks up on you.
Risk management in real life (not the textbook version).
Why mindful consumption isn’t about cutting back, but tuning in.
What makes retirement joyful beyond the spreadsheets.
How your community can be the most underrated part of your portfolio.

If you’ve felt a little off-course—or just want a chance to recalibrate without the guilt trip—this episode delivers practical steps and encouraging reminders to help you make the second half of 2025 your strongest yet.

Got goals? Let’s reset ‘em. And if not, we’ve got a few ideas for those, too.

FULL SHOW NOTES: https://stackingbenjamins.com/our-review-of-first-half-2025-1708

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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The Stuff You Should Stop Buying (and Why Your Wallet Will Thank You) SB1707 Jul 11, 2025

Show notes

Is your house full of stuff you thought you needed… but haven’t touched since the Obama administration? In this game show-style episode, we're helping you clean house and bulk up your bank account at the same time.

Joining Joe in the basement are Paula Pant from Afford Anything, OG, and the man, the myth, the TikTok-famous legend’s grandpa’s best friend: Len Penzo (or as Doug calls him, “America’s Most Unexpected Influencer”). Together, they go head-to-head in a raucous showdown, each offering hot takes on everyday items you should stop buying if you want to save money and ditch the clutter.

We dig into:

Why some exercise equipment becomes expensive coat racks
The hidden costs of seasonal decorations
Periodicals, subscriptions, and other budget vampires
And a few “who knew?” items that quietly drain your cash

You'll also get a dose of trivia, debates about Google's "search decay," and a few personal stories that might sound a little too familiar.

Whether you’re decluttering your budget or just here for the basement chaos, this episode is full of laughs, lightbulb moments, and ideas to help streamline your spending.

FULL SHOW NOTES: https://stackingbenjamins.com/decluttering-your-financial-life-greatest-hits-1707

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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Happy Money, Hidden Fees, and Hiring Your Kids (SB1706) Jul 09, 2025

Show notes

What if your money could bring you more joy—and less stress? Today, we welcome Ken Honda, Japan’s bestselling personal development guru, to the basement. He introduces us to his concept of “Happy Money,” where gratitude replaces fear, and your relationship with money becomes… well, happier. From early lessons in emotional finance to wisdom from his own mentors, Ken shares how small mindset shifts can lead to big life changes.

But before we get zen with our Benjamins, Joe and OG shine a light on the latest investigation into real estate commissions. Are hidden fees quietly draining your wallet when you buy or sell a home? The Justice Department seems to think so. We dive into what’s happening—and what you can do about it.

Also in the episode:

HSA contribution limits are rising—are you using your health savings account the smart way?
A listener wonders if hiring their kids can unlock Roth IRA opportunities (spoiler: it’s not as simple as “just write them a check”).
Doug moonshines a trivia question that may or may not involve death (but definitely involves Doug).

Whether you’re looking for practical strategies or a new perspective on money itself, this episode brings both insight and inspiration.

FULL SHOW NOTES: https://stackingbenjamins.com/happiness-with-ken-honda-greatest-hits-1706

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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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Want More Money? Cut The Clutter (with Tracy McCubbin) SB1705 Jul 07, 2025

Show notes

Is your home packed with emotional baggage... and maybe a few fondue sets you haven’t touched since 2003? Organizational expert Tracy McCubbin joins us to talk about the emotional side of clutter—why it builds up, how it weighs us down, and what to do when your sentimental stuff is quietly running the show.

Meanwhile, Joe and OG dig into another kind of mess: the billions retirees lose by claiming Social Security too early. Timing isn’t just everything—it’s the difference between thriving in retirement and wondering where all the money went.

In this episode, we cover:

Why sentimental clutter is more than just "stuff"—and how to finally let it go.
How donating intentionally can breathe new life into your old things (and clear some mental space).
The tough conversations adult kids need to have with parents about downsizing and letting go.
Strategies to help you avoid making costly Social Security decisions.
A surprisingly thoughtful take on the Taco Bell Hotel (yes, it’s real... and yes, it sold out in minutes).

Plus: a listener question, some truly questionable fashion choices, and one more reason not to hoard your retirement benefits—or your holiday dishes.

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Let's Start a Money Revolution (SB1704) Jul 04, 2025

Show notes

Happy Independence Day, Stackers! While fireworks boom and flags wave, we're lighting a spark under your financial life. This episode isn’t about tea in harbors—it’s about burning down debt, revolting against lifestyle creep, and rallying your family for a better money future.

Joining Joe and Doug in the basement for this full-on financial insurrection:

Dorethia Kelly, TikTok titan and money coach, shares how she raised her financial flag as a single mom and became a force for smart money choices.
Jesse Cramer of the Personal Finance for Long-Term Investors podcast ditches tired spending habits and charts a course for independence through intentional investing and budgeting.
Steve Stewart, longtime SB editor and podcasting Yoda, reveals the pivotal Jeep moment that changed his financial course—and why he's racing OG to mortgage freedom.

🎙️ In this basement-based revolution, you'll hear:

The financial “tea party” moments that woke our guests up to their money mess
How to declare independence from credit cards, lifestyle creep, and sneaky “Buy Now, Pay Later” traps
Tools, mindsets, and support systems that help you keep your financial revolution alive
Why tax planning is the financial Boston Tea Party nobody's talking about
The trivia showdown no revolutionary should miss: How many grains of silver made a dollar in 1792? (Spoiler: Jesse knows his colonial coinage.)

And in the aftershow? We ask the deep questions our Founding Fathers never saw coming, like: why is gambling debt dischargeable in bankruptcy, but student loans aren't?

FULL SHOW NOTES: https://stackingbenjamins.com/financial-independence-day-2025-1704

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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Turning Ideas into Billion Dollar Businesses (with Julie Wainwright) SB1703 Jul 02, 2025

Show notes

What does it take to turn a bold idea into a billion-dollar brand? Julie Wainwright, founder of The RealReal, joins us to share how she did just that—after enduring some pretty public failures (hello, Pets.com). She talks about navigating the startup world, tackling ageism head-on, and why your past doesn’t define your future.

Julie’s story is packed with wisdom on risk-taking, confidence, and what it really means to build something new when everyone else is telling you no. From the boardroom to the resale boutique, she takes us through the emotional rollercoaster of entrepreneurship—plus a few secrets on why luxury goods are more than just a pretty label.

Also in the basement:

We unpack Jason Zweig’s latest Wall Street Journal column on diversification and why it still matters (yes, even in this market).
OG learns a Father’s Day lesson on the golf course (spoiler: not all swings are created equal).
Doug manages to work in Margot Robbie. Again.

Whether you’re plotting your own business empire or just wondering how someone not only recovers from flaming sock puppet-level failure, but who THRIVES afterward, this episode delivers honest insight with a side of style.

FULL SHOW NOTES: https://www.stackingbenjamins.com/from-business-idea-to-execution-julie-wainwright-1703/

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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Is the 4% Rule In Play? (SB1702) Jun 30, 2025

Show notes

How much can you really spend in retirement without running out of money—or worse, running out of fun?

In this deeper-than-usual dive, Joe Saul-Sehy and OG examine the classic 4% retirement rule and whether it’s time for an upgrade. With new commentary from Bill Bengen, the original architect of the 4% rule, the team explores emerging research that suggests a withdrawal rate closer to 5.5% might be possible—if you’ve got the right mix of investments, a solid plan, and a bit of courage.

But we don’t stop there. Because with greater freedom comes greater risk (especially if you're leading with vibes instead of strategy). The guys tackle the sequence of returns risk that can derail early retirement years, and how to build a portfolio that helps you sleep at night—even during a market storm.

Meanwhile, Doug drops in with an unexpected (and very British) culinary experience, Joe fields a listener question comparing financial plans to workout routines (is your Roth IRA doing enough reps?), and yes... we revisit our fan-favorite segment on how food waste is wrecking your budget.

Why the 4% rule might be too conservative (or maybe just outdated).
What diversified portfolios and asset class strategy have to do with a longer-lasting nest egg.
How to prepare for market downturns before they happen—and what to do if you're already in one.
Why retirement joy isn’t just about spreadsheets—it’s about the psychology of spending with confidence.
Which type of green tea is the superior kind (depending on which side of the TikTok aisle you're on).
How to reduce food waste and put that extra savings toward your bigger financial goals.

If you’re approaching retirement—or even just dreaming about it—understanding how much you can safely spend without sabotaging your future is the question. This episode combines historical insight with today’s market realities to give you the real math and mindset you need to retire well…and maybe even with a smile.

FULL SHOW NOTES: https://stackingbenjamins.com/problems-with-the-4-percent-rule-1702

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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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Are Money Gurus Feeding Us Lies? (SB1701) Jun 27, 2025

Show notes

Can you really build wealth with a simple formula? Do you need a budget to succeed financially? Should you cut up all your credit cards, or is that just a dramatic TikTok trend?

In this episode of The Stacking Benjamins Show, Joe Saul-Sehy is joined by Paula Pant, Doc G (Jordan Grumet), and Jesse Cramer for a roundtable discussion that peels back the truth behind popular advice from so-called financial “gurus.” The conversation is rooted in a provocative blog post by Christine Luken that calls out four common money mantras—and the team dives into each one with classic basement wit, spirited debate, and hard-earned wisdom.

Topics on the table:

Do you really need a budget, or can you thrive without one?
Are rigid financial formulas helpful or harmful?
Is willpower the key to financial success—or just a scapegoat?
Does cutting up credit cards actually solve your spending problems?

Along the way, you'll hear banana jokes (yes, multiple), a heated trivia contest about obsolete technology (looking at you, LaserDisc), and some good-natured trash talk that might just surprise you with how insightful it gets.

This episode is packed with nuance, laughs, and practical takeaways for Stackers who are tired of the one-size-fits-all guru approach. Whether you’re team budget or team spreadsheet freestyle, there’s something here for you—plus a solid reminder that when it comes to personal finance, the best advice is the advice that fits your life.

FULL SHOW NOTES: https://stackingbenjamins.com/lies-damn-lies-and-statistics-1701

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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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.