The Stacking Benjamins Show – Details, episodes & analysis

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The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP

Business

Education

Frequency: 1 episode/2d. Total Eps: 1518

Named Best Personal Finance Podcast by Bankrate.com and Kiplinger — and the only podcast the Plutus Awards retired from competition after winning twice — The Stacking Benjamins Show is personal finance that doesn’t put you to sleep.

Hosts Joe Saul-Sehy (former 16-year financial advisor, ex-WXYZ-TV “Money Man”) and Josh “OG” Bannerman, CFP (Certified Financial Planner, Bannerman Wealth) sit around the card table in Joe’s mom’s half-finished basement in Texarkana and talk money with the smartest guests in personal finance, investing, and behavioral economics. As Fast Company wrote, the show “strikes a great balance of fun and functional.”

Every Monday, Wednesday, and Friday: expert guests, real headlines, listener questions, and Doug’s trivia. Topics include investing, retirement planning, budgeting, real estate, behavioral finance, taxes, and financial independence — for anyone who wants to be smarter about money without being talked down to.

Subscribe to The 201 — the free newsletter that goes deeper than the show — at stackingbenjamins.com/201

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https://www.StackingBenjamins.com/201
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http://stackingbenjamins.com/havenlife
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http://linkedin.com/sb
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http://linkedin.com/SB
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https://www.amazon.com/Behavioral-Investor-Daniel-Crosby-ebook/dp/B07HH99WH8
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Invest Like the 1%? What to Steal, What to Scale, and What to Skip (SB1836)

Episode 1836

Friday, May 1, 2026 • Duration 56:52

You've seen the ads. Invest like the ultra-wealthy. Get access to what the 1% does. But what does the 1% actually do -- and how much of it should a normal person try to copy? Joe, OG, comedian and finance educator Roxanne Duckels, and Jesse Cramer run every popular "rich people investing" idea through a simple filter: steal it, scale it, or skip it. The answers will surprise you -- especially the one where OG wants to delete an entire asset class from existence.

What You'll Walk Away With

Why long-term thinking is the one habit the 1% has that every Stacker should steal immediately -- and the short-term execution piece most people miss when they try
The tax strategy obsession that the wealthy genuinely use -- and why Jesse ranks it seventh on his list of financial priorities, not first
What paying for advice actually means when you're smart enough to do it yourself -- and why the wealthiest people surround themselves with even smarter people anyway
The alternative investment marketing trap hiding inside every "invest like the rich" pitch -- and OG's case for why most people have no business touching any of it
Why the accredited investor designation protects almost no one -- and what the real risk is when you lock up money in illiquid investments chasing slightly better returns
The leverage conversation that exposes a contradiction hiding in plain sight for every real estate investor
Why Roxanne's path to financial independence started with filling her gas tank all the way up -- and what that tells you about long-term thinking at any income level
The one question that should precede any alternative investment conversation: does the expected return actually beat what publicly traded equities already offer?
What the trivia competition scoreboard looks like heading into the back half of the year -- and whether OG's historic lead is as safe as it looks
Why rich habits and "what the 1% does" are two completely different things -- and which one is actually worth chasing

Why This Matters Now

In a noisy market environment, the "invest like the wealthy" pitch gets louder every time volatility spikes. Private credit, non-traded REITs, leveraged real estate, alternative assets -- the marketing machine never stops. For Stackers in their 40s who've built something real and don't want to blow it chasing a category that mostly benefits the people selling it, this episode is a useful reset. The habits worth stealing from the 1% turn out to be remarkably unglamorous.

From the Basement

Joe, OG, Roxanne Duckels from Finance Rox, and Jesse Cramer run the "invest like the rich" playbook through a steal-it-scale-it-skip-it framework -- and nobody agrees on everything, which is exactly what makes it useful. Doug arrives with Mayday trivia about the origin of the distress call and the year it was coined, which turns into one of the cleaner trivia finishes of the season. Whether the basement scoreboard moved in OG's favor or Jesse closed the gap is a question best answered with your earbuds in.

Resources Mentioned

Finance Rox -- Roxanne Duckels on YouTube and Instagram @FinanceROX
Personal Finance for Long-Term Investors -- Jesse Cramer's podcast, wherever you listen
Stacking Benjamins Newsletter (The 201) -- recent issue: brokerage vs. UTMA/UGMA vs. Trump accounts for kids; stackingbenjamins.com/201
Stacking Benjamins Vault -- stackingbenjamins.com/vault
Stacking Benjamins Community -- stackingbenjamins.com/basement
Stacking Benjamins Meetups -- stackingbenjamins.com/bad

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Mrs. Dow Jones on How to Become a Future Rich Person (Without Giving Up Your Life) SB1835

Episode 1835

Wednesday, April 29, 2026 • Duration 01:03:39

Haley Sacks didn't grow up knowing what a 401k was. She was nannying for a kid named Winthrop on the Upper East Side, doing comedy at night, and getting paid cash under the table. Then she sat in an HR meeting and her eyes glazed over -- and she decided that was the last time she'd be caught unprepared with her own money. Today she's Mrs. Dow Jones, with millions of followers and a new book. The basement finally got her in the chair, and she did not hold back.

What You'll Walk Away With

The "future rich person" framework -- what separates people quietly building wealth from everyone else performing it
Why the biggest wealth trap isn't overspending -- it's the psychological pull of looking rich before you are
How automation is the real secret behind Haley's path to millionaire status -- and why willpower alone was never going to get her there
The action movie analogy that finally makes the debt-versus-investing debate make sense -- and which one you tackle first
Why your fixed expenses might be the actual problem -- and the two levers you can pull when the math doesn't work
The "money date" habit that keeps Haley on track -- and how to make it something you'll actually do every month
What a mise en place approach to your finances looks like -- and the four accounts every future rich person needs in place before anything else
Why cutting spending has a floor but earning more doesn't -- and how to think creatively about your income ceiling
The mortgage volatility conversation hiding in this episode -- including OG's take on where rates actually belong historically and why "date the rate" might be the most useful three words in real estate right now
Why comparison is derailing more financial plans than bad investments ever could

Why This Matters Now

If you're in your 40s and you still feel like the millionaire milestone belongs to someone else's story -- someone who started earlier, earned more, or just had better instincts -- this episode is a direct challenge to that belief. Hailey Sacks didn't have better instincts. She had a glazed-over HR meeting and a determination not to be caught unprepared twice. The foundation she built after that moment is exactly what she walks through today.

Why You Should Stop Saving for Retirement 3 Years Early (SB1826)

Episode 1826

Wednesday, April 8, 2026 • Duration 01:13:37

Retirement expert Jamie Hopkins has spent 20 years helping people plan for retirement, and his most counterintuitive advice stops most savers cold: in the final years before you retire, putting more money away might actually be hurting you. This week he joins Joe and OG to explain why, and what to do instead.

In this episode:

Why financially prepared retirees still end up miserable, how to practice spending before you retire, the home bias that quietly tanks your portfolio and your quality of life at the same time, and what to actually do with all that home equity when the time comes.

Biggest takeaways:

The last three to five years of extra contributions barely move the needle on your retirement portfolio. Working six months longer matters more. So does learning to spend. Take that money and actually use it, so you're not hitting retirement having never practiced.

Retirement isn't a math problem, it's an identity problem. The people who struggle most aren't broke. They never figured out where their purpose and community would come from once work disappeared.

Over half of Americans are forced into retirement earlier than expected. You need a plan for that scenario now, not when it happens.

Resources mentioned:

Jamie Hopkins' Retirement Sketchbook wherever books are sold
The Stacking Benjamins scorecard: stackingbenjamins.com/scorecard
The Vault: stackingbenjamins.com/vault

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David Gardner on Breaking the Rules of Investing (SB1736)

Wednesday, September 17, 2025 • Duration 01:26:45

What happens when you stop playing it safe and start playing it smart? In this episode, Joe Saul-Sehy, OG, and Neighbor Doug sit down with David Gardner, co-founder of The Motley Fool, to explore how breaking traditional investing “rules” can sometimes lead to the biggest wins. From his early career to building a community of investors who think differently, David shares the lessons that shaped his approach and why focusing on long-term investing (with a dash of joy) is the key to building wealth.

This isn’t just theory—David opens up about the real-world evolution of financial advice, the importance of conscious capitalism, and why advisors need to shift from just picking stocks to becoming true guides in an era where investment products are commodities. Along the way, the basement crew mixes in a few unexpected detours (yes, including some movie talk), reminding us that money doesn’t have to be boring to be meaningful.

If you’ve ever felt like the “safe” path with your money was leading you in circles, this episode offers a fresh perspective from one of the most influential voices in modern investing. Get ready to rethink the rules, laugh along the way, and come away with strategies to make your portfolio—and your life—more rewarding.

Why breaking conventional investing “rules” can sometimes be your best move
The evolution of The Motley Fool and its impact on everyday investors
How long-term thinking beats short-term noise in building wealth
The role of conscious capitalism and why businesses matter beyond profits
Why financial advisors need to pivot their focus to guidance, not just products
How criticism shaped David Gardner’s career and what he learned from it

Points to Ponder During the Episode

When’s the last time you broke a “money rule,” and did it pay off—or backfire?
Do you believe financial advisors should focus more on guidance than investment selection?

The 4 Cornerstones of a Successful Financial Strategy (with CFP Brian Ursu)

Monday, March 9, 2020 • Duration 01:18:23

What's your financial plan? Is it built on bedrock or are you "winging it", aka building on sand? On today's show, Certified Financial Planner Brian Ursu joins us to dive into four strategies that will help anyone trying to build their financial house. For veteran planners, these will be things you've heard before. However, the question isn't, "Have you heard them?" Like anything, you should ask yourself, "Am I doing them?" THAT may yield a completely different answer.

Plus, TurboTax maker Intuit has been in the news recently, because they're buying credit score site Credit Karma. What does that mean for consumers like us? Also, because Credit Karma is a FinTech company, what does that mean for FinTech? We'll ask Ryan Falvey from Financial Venture Studio both of those questions. If you've heard Ryan before on our show, you know he'll have an interesting point of view.

Of course, that's not all. We'll throw out the Haven Life line to a lucky listener AND still leave time for Doug's trivia...which today takes a more-than-usual unusual twist.

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The Biggest Lie In Personal Finance (plus and intro to the Retirement Budget Calculator)

Friday, March 6, 2020 • Duration 01:28:36

If you believe telling a white lie is okay, do you believe that about money topics? What about white lies that are told by big-time bloggers or (gasp) podcasters about the path to riches? We'll dive into the world of lies and deceit on today's show with an all-star cast around the rickety card table. Joining us today we welcome Dustin Heiner from The Master Passive Income Podcast, Paula Pant from the Afford Anything Podcast, and from our very own podcast, OG!

We know a lot of you use calculators for your job, but we think you will all like using the Retirement Budget Calculator after hours as well. During our Friday FinTech segment, Joe will talk with Jason Parker from the Sound Retirement Planning podcast. They'll discuss how Jason's Retirement Budget Calculator has continued to grow. Joe last year said that this calculator was the "best retirement calculator for consumers" (he still thinks there are better calculators for pros). We'll have all the details on how it works AND share some discounts you won't get if you buy the calculator elsewhere.

And finally, during our MagnifyMoney segment we will answer a question via Twitter. What is your best advice for future college students to fund their education when their parents can't or won't help them? There's SO much more...but you'll have to listen to hear it all! Hope you can join the fun.

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Want to Increase Your Earning Power? Learn To Speak Better (with Grant Baldwin)

Wednesday, March 4, 2020 • Duration 59:41

It's your big moment. You're talking to the boss or giving a presentation at work. Maybe you're finally in front of your dream customer. And you blow it. Today we'll help you earn more money by focusing (well, as much as we focus...) on speaking well. Whether you're trying to convince the family to wash dishes or your boss to give you a raise, speaking more effectively is far from a "soft" skill. So today we welcome Grant Baldwin, author of The Successful Speaker, and host of the Speaker Lab podcast to give us some tips and tricks!

How does Social Security look? During our headline segment, we'll dive into that topic, and run through the future of Social Security. How long will stay solvent? And, in the most important question anyone has asked around here today, we'll ask, "How did a couple of guys score free McDonald's?" Just another day on our show.

If you think that's all, it might be your first time here (so welcome!). Of course, we'll throw out the Haven Life line to a lucky caller, share some of Doug's amazing trivia AND much, much more. Enjoy!

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Cracking The Whip On Your Financial Goals (with Lindsay Goldwert)

Monday, March 2, 2020 • Duration 01:15:39

Do you have trouble staying in charge of your money? Maybe you let your priorities get away from you and want to make a change? Today we'll talk about communication, being direct, and asking for what you really want with the author of the hit new book Bow Down, Lindsay Goldwert. In this unique new perspective on how to take charge, Lindsay sat down with dominatrixes across America to get first-hand information on how you can "reset the power dynamic in any situation to get what you want—whether it’s from a husband, boss, or partner."

During our headlines segment, are you finally bringing in a HUGE nice income, but your bank account isn't rising? Lifestyle inflation can become a serious issue for high earners, and without a proper plan in place investors run the risk of becoming a HENRY - High Earner, Not Rich Yet. Plus, during our second headline, we'll touch on why actor Rick Moranis is making a return to the big screen and what lessons you can glean for your financial plan.

Plus, we'll open up the mailbag during our Haven Life Line and answer an estate-related question from Diana. Diana is the executrix of an estate plan for the funds of two pre-teens but wants to appoint someone else to take over most of the responsibilities. What can she do? What is she supposed to do? We'll cover some estate planning basics on today's show.

And, of course, we'll also make some time for Doug's trivia. Enjoy!

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What To Do When the Bull Market Finally Ends (SB RWD 104)

Friday, February 28, 2020 • Duration 01:06:18

There's been a lot of market fears going around this past week, but regardless of its origin people have been asking the same question for years: what should we do when the bull market finally ends? We're finishing out the rewind week with one of our classic old-school roundtable episodes featuring Paula Pant, Len Penzo, and Greg McFarlane answering that very question. You can read the original show notes below:

This has been a LONG bull market. So if you know that the next eight years will most probably NOT be like the previous eight, do you swap out some of your investments? We ask our roundtable panel that on today's show and as always, find Greg, Len and Paula all have different answers than you probably expected.

We also tackle lifestyle paradigms. Are you paying too much attention to your neighbor's success? Finally, we'll discuss fake news....no, we aren't going politics. We'll ask our panel whether there's any "fake news" in the money area that they're sick of hearing. Of course, they come through with some great examples.

In our Freshbooks FinTech segment we talk to SelfLender CEO James Garvey about building credit. How does SelfLender help people find financial footing? They have an interesting idea and an exciting approach. Can't wait for you to hear all about it.

Thanks to SoFi and MagnifyMoney.com for sponsoring our show!

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The #1 Key To Get Someone Excited About Saving Money - SB RWD 103

Wednesday, February 26, 2020 • Duration 01:06:19

Are you committed to saving, but can't seem to get other people around you on board? It can be frustrating once investing for the future has clicked in your head, but not for the people you care about. Gene Natali, co-author of The Missing Semester, shared some great information with us on how to get anyone interested in saving for the future and we're revisiting that interview today. You can read our original show notes below:

You're excited about saving, but how do you get someone else to take the plunge? Today's guest, Gene Natali, says that the answer might not be what you expect, and he should know. He co-authored the book The Missing Semester about personal financial education in the classroom, and he's BACK on the Stacking Benjamins show to share how to get ANYONE started in the right direction with their money.

In our headlines segment, we talk about financial advisory fees. Are they going down? A recent report has details on where that ship is headed. Also, we'll talk about the age-old active vs. passive management debate. Do active managers hold a candle to passive? Does it matter? Then we throw out the Haven Life line to Dan, who asks about EE bonds. Are these bonds a great way to protect against deflation? We'll also answer a letter from Todd, who has some extra money and wants to know how to invest it...other than in sending it to his favorite podcasters (#disappointing).

It's National Martini Day, so Doug's pouring drinks down in the basement and we're all invited over. Come join us!

Special thanks to M1Finance for sponsoring our show! We couldn't do any of this without the support of some pretty awesome companies.

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The Stacking Benjamins Show – Details, episodes & analysis

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The Stacking Benjamins Show – Details, episodes & analysis

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