The Stacking Benjamins Show

Latest Episodes:

Harvard Business Review's Kevin Evers on the Genius of Taylor Swift (SB1671) Apr 16, 2025

Show notes

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, 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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Money and Business Lessons from the Career of Taylor Swift (and a BIG Roth IRA rule clarified) SB1670 Apr 14, 2025

Show notes

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 to the troops, and a shoutout to basement podcasters
A colonoscopy story you didn’t ask for, but will absolutely remember

Whether you’re a Swiftie, an investor, or just here for the financial clarity, this episode brings strategy, insight, and unexpected takeaways you can actually use.

FULL SHOW NOTES: https://stackingbenjamins.com/the-strategic-genius-of-taylor-swift-1669

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.

Conquering Investment Fears and Risks (SB1669) Apr 11, 2025

Show notes

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.

💡 What’s inside:

Why market risk feels scary—but often isn’t the real danger
How liquidity and time horizon risks can quietly erode your strategy
The danger of overconcentration (ahem, putting all your eggs in one ETF)
What inflation, reinvestment, and credit risk mean for your future
How to navigate longevity and foreign investment risks without flinching

And of course, the basement wouldn’t be the basement without a few detours—including a surprise milkshake debate and Doug’s trivia segment that takes a sharp left into apple peels, Johnny Appleseed, and questionable coalition logic.

If you’re ready to face the real dangers of investing—and stop fearing the ones that don’t deserve your attention—this episode’s got you covered.

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 To Smooth Out Your Investing Ride...or not (SB1668) Apr 09, 2025

Show notes

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?

🧠 In this episode:

How to hedge against market swings without panicking
Why keeping it simple could beat fancy fund strategies
What most investors get wrong about stock market “danger”
The power of a long-term mindset and how it pays off
Tips for building confidence in your own investment decisions

We also take a break for the TikTok Minute (yes, we found another gem), and Doug brings a trivia challenge that'll take you back to the dawn of the space race.

And later, we open the mailbag:

A listener asks how to plan solo for retirement
...and also wonders how much is too much for an emergency fund

It’s a full basement session—investing insights, listener Q&A, and a few unexpected left turns.

FULL SHOW NOTES: https://stackingbenjamins.com/talking-about-taxes-and-tariffs-in-your-investment-plan-1667

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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Special Episode: Tariff Fallout - What Should You Do? Apr 08, 2025

Show notes

Tariffs got you sweating? We’ve got the strategy (and the LaCroix) to help you chill.

Markets are wobbling, headlines are screaming, and you’re wondering if your portfolio is about to implode. Take a deep breath—and head down to the basement.

In this episode, Joe Saul-Sehy, OG, and Mom’s neighbor Doug tackle the turbulence triggered by recent tariff changes. While others panic, we’re pouring the coffee and walking you through how to think smarter (and sleep better) during uncertain times.

🔍 Inside the episode:

What recent tariff changes actually mean for your money
How to protect your investments when markets get shaky
Why doing nothing might be the smartest move
The behavioral traps investors fall into—and how to avoid them
Reassurance, real talk, and your weekly dose of Doug

Whether you’re tempted to sell it all or just want a little peace of mind, this episode gives you tools to stay cool, stay invested, and stay the course.

Because in the basement, we don’t panic—we plan.

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From Basement Beginnings to Million-Dollar Dreams (with Rudy Mawer) SB1666 Apr 07, 2025

Show notes

Entrepreneurship, financial anxiety, and a guinea pig (yes, really).

When you’ve got a stuffed guinea pig on your desk and a mic in front of you, it’s only a matter of time before you talk about that one time you ate guinea pig in Peru. (Spoiler: It was pretty good.) That’s how we open today’s show—but from there, things get real.

Today’s main event features Rudy Mawer, founder of 60 Day Hustle, who joins Joe Saul-Sehy to share his incredible story. Rudy grew up in a modest home in England, raised by two world-class triathletes who pushed him to pursue excellence. He didn’t come from wealth—but he did build it, and fast. Rudy opens up about:

His path from sports scientist to serial entrepreneur
The role mentorship and strategic networking played in his success
Why legacy matters just as much as hustle
His latest documentary project and what drives him today

Then, we turn to a conversation sparked by actor Seth Rogen’s recent interview with Dax Shepard. Rogen confessed he’s spent years saving out of fear—and maybe missed out on life in the process. So we ask:

Are you hoarding cash out of anxiety?
What happens when your savings plan becomes a cage?
And how can Stackers find balance between security and spontaneity?

Finally, we wrap up with one heck of a weather report. Mom’s neighbor Doug recounts the epic ice storm that left him snowed in, powered down, and questioning all his life choices. (Okay, maybe not all of them—but definitely his chainsaw strategy.)

As always, Doug brings the trivia heat (and a little airline history), and we share some listener reflections that tie it all together.

It’s a jam-packed episode—from financial fear to frozen driveways—with a little Peruvian culinary adventure tossed in.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-get-moving-on-your-money-goals-rudy-mawer-1666

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.

BIG Questions In Finance: Are You IN or OUT? (SB1665) Apr 04, 2025

Show notes

Is good debt a myth? Should we all chase FIRE? The basement panel weighs in.

In today’s Financial Concepts Friday roundtable, Joe brings the basement crew together for a lively “In or Out” debate on some of the most polarizing personal finance topics out there. Are we in or out on the idea of “good debt”? Do budgets really matter when you’re just starting out? Should you talk about money with your friends and family… or is that still taboo?

Joining Joe are three financial thinkers who aren’t afraid to stir the pot:

Paula Pant from Afford Anything
Jesse Cramer from The Personal Finance for Long Term Investors Show
OG from our own basement think tank (and planning headquarters)

Together, they dig into:

Whether any debt can actually be considered good
If living without a budget is a fast track to financial regret—or freedom
The upside (and awkwardness) of open money conversations
How FIRE goals like retiring by 35 sound… and feel, once you really unpack them

Plus, Mom’s neighbor Doug drops by with a trivia challenge that’ll have you laughing (and maybe yelling at your speaker). And of course, we wrap up with reflections that’ll leave you both entertained and a little bit wiser.

So grab a LaCroix from the mini fridge and join us in the basement—this one’s packed with laughs, insights, and hot takes on cold, hard cash.

FULL SHOW NOTES: https://stackingbenjamins.com/personal-finance-most-controversial-questions-1665

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.

Top 5 Eye-Roll Financial Tips You Should Ignore SB1664 Apr 02, 2025

Show notes

Ever been told to buy the biggest house you can afford... to “motivate yourself”? Or to skip insurance because “nothing bad will happen”? Yeah—us too. And we’ve got some thoughts.

In this episode, Joe, OG, and Doug break down the Top 5 Worst Financial Tips they’ve ever heard—and more importantly, why taking them seriously could leave your finances in a flaming dumpster behind your dreams.

From personal debt confessions to debates about extreme couponing, bad budgeting ideas, and the wild world of TikTok money myths, this episode is your roadmap to not falling for advice that sounds smart but… absolutely isn’t.

In this episode:

Why “buying big” won’t necessarily inspire you—it might just bankrupt you
Skipping insurance to save money? We’ll show you how that plan ends
Should couples really share just one checkbook? We investigate
The great emergency fund vs. credit card debate
When DIY everything turns into Why Did I Try?
How the satire in The Joneses movie is secretly more real than you think
Listener Q&A: Impact investing, private debt financing, and what it means to be an accredited investor
Plus, a surprise TikTok moment, OG's thoughts on calendars, Doug’s history of April Fools’ disasters, and much more

You’ll laugh, you’ll learn, and by the end, you’ll be a whole lot more confident dodging bad advice in the wild.

🎧 Tune in and stack smarter by skipping the “advice” that could sink your stack.

FULL SHOW NOTES: https://stackingbenjamins.com/our-top-five-money-saving-solutions-1664

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.

Tiffany Aliche on Connections and Financial Wholeness (with a side discussion on recent DoorDash/Klarna news) SB1663 Mar 31, 2025

Show notes

Is financial literacy missing from your life like that sock you swear went in the dryer? Tiffany Aliche, AKA The Budgetnista, is here to help you find it—minus the lint. She shares her journey to financial wholeness and takes us behind the scenes of her brand-new PBS special.

Meanwhile, Joe and OG break down why financial education starts with community (not overpriced guru courses), why ‘Buy Now, Pay Later’ is the financial equivalent of eating fast food in your car—feels great now, but you’ll regret it later—and how even a trip to Texarkana can teach you a thing or two about money. Plus, a story involving World War II espionage that somehow made its way into the mix.

Here’s what’s on tap this week:

Kicking off Monday with a solid dose of grumpiness (and a passionate store-brand rant).
Hanging with The Budgetnista—Tiffany Aliche takes us behind the scenes.
Why financial literacy isn’t just about numbers—it’s about community.
The sneaky financial traps that might be eating your wallet alive.
Tiffany’s PBS special—how she tackled stage fright and delivered a knockout show.
Headlines that made us go “Wait, WHAT?!”—including Klarna and DoorDash teaming up.
‘Buy Now, Pay Later’—why it’s like borrowing money from Future You (and Future You is not happy about it).
Mortgage strategies, financial independence, and the art of dodging debt.
Could you survive a week on cash only? One of us is trying (and maybe crying).
Food waste: it’s not just bad for the planet—it’s silently draining your bank account.
Upcoming meetups, tax tips, and basement-style money wisdom you can actually use.

And if you stick around long enough, well… who knows what else might show up?

FULL SHOW NOTES: https://stackingbenjamins.com/budgetnista-financial-literacy-1663

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

Enjoy!

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

Better Investing Using Horrible Investment Products (SB1662) Mar 28, 2025

Show notes

Ever fallen for an investment that seemed like a sure thing... until it wasn’t? You’re not alone. Today, we shine a light on some of the worst investment advice out there—and help you steer clear of it.

Joining Joe at the roundtable are:

Paula Pant from Afford Anything
Jesse Cramer from Personal Finance for Long-Term Investors
And Don McDonald, financial pro and former astronaut (not really, but just go with it) from Talking Real Money.

Infinite banking and other shiny traps – What sounds like genius often comes with fine print you’ll wish you’d read.

Penny stocks and the illusion of easy money – Spoiler: if it feels like a shortcut, it's probably a detour.

Equity-indexed annuities and their slick sales tactics – When someone tells you there’s “no downside,” maybe run.

Gut feelings vs. data – The panel weighs in on trusting instincts vs. trusting actual math.

Teachers and 403(b) plans – A quick peek behind the curtain at one of the most overlooked problem areas in personal finance.

How not to invest – A rundown of red flags and hard-won wisdom from people who’ve seen the worst up close.

Meanwhile, Doug brings the trivia thunder with a question about sitcom salaries—and things quickly go from Big Bang to big bucks.

Whether you’ve made a misstep or are just trying to avoid one, this episode will help you tune out the noise, spot the nonsense, and build a smarter, more resilient investment plan.

FULL SHOW NOTES: https://stackingbenjamins.com/our-least-favorite-investments-1662

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

Enjoy!

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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