The Stacking Benjamins Show

Latest Episodes:

How NOT To Invest: Lessons from Barry Ritholtz SB1661 Mar 26, 2025

Show notes

Ever wondered how the top financial minds avoid disaster while the rest of us are busy panic-Googling “best investments 2024”? Today, Joe welcomes Barry Ritholtz of Ritholtz Wealth Management down to Mom’s basement for a conversation that flips typical investment advice on its head. It’s not about what to do—it’s about what not to do if you want to grow your money without losing your sanity.

Barry shares battle-tested insights from his years in the trenches, covering everything from behavioral finance to market psychology and how to avoid falling for trends that make great headlines but terrible portfolios.

Also in this episode:

Subscription hacks you didn’t know you needed (and yes, even that one you've been ignoring since 2021).

How market history can be your secret weapon—if you actually pay attention to it.

Tech innovations in finance and why Barry says they're both exciting and a little terrifying.

Productivity gains, AI, and whether the future is a robot that trades ETFs for you while you nap.

A peek into Barry’s latest book and the big idea that might shift how you think about investing.

Doug creates yet another national holiday—because what the world needs now is Bow Chicka Wow Wow Day.

Stacker mailbag time! We’re diving into job loss strategies, building bulletproof emergency funds, and yes, getting into the weeds with buffer ETFs.

The never-ending showdown: remote work vs. office life—where do Stackers land?

And of course, Doug’s trivia will challenge your financial knowledge and possibly your respect for faux holidays.

Whether you’re a seasoned investor or just now figuring out what a 401(k) actually does, this episode brings the insight, laughs, and community you’ve come to expect from the basement.

🎧 Tune in and stack smarter—with fewer missteps and a whole lot more fun.

FULL SHOW NOTES: https://stackingbenjamins.com/getting-your-investments-right-with-barry-ritholtz-1661

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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10 Ways to Stop Blowing Up Your Investment Portfolio (SB1660) Mar 24, 2025

Show notes

What do weddings, wineries, and Whoppers have to do with smart investing? This week, Joe, OG, and Doug kick off the episode with stories from the road—including a surprise credit card confession that somehow involves a Burger King (because of course it does).

But then the gang shifts gears and dives into real money talk, breaking down investing wisdom from the legendary Barry Ritholtz. From navigating market cycles to keeping your emotions in check, Barry’s top 10 tips serve up the kind of grounded, no-BS advice your portfolio will thank you for—especially the next time the market gets jumpy or the headlines go haywire.

They also tackle what politics really mean for your investments (spoiler: maybe less than you think) and why getting your expectations right could be the most important investment decision you make.

Stick around to hear a listener question that hits close to home: How should you invest for an 84-year-old mom? It’s a multigenerational money moment that brings the discussion full circle.

Here’s what you’ll learn:

Why market cycles matter (and how to avoid getting whiplash)

The hidden dangers of investing with your heart instead of your head

What Barry Ritholtz says about predicting political impacts on your portfolio

How to set realistic return expectations (and why that’s surprisingly freeing)

A practical investing strategy for elderly parents—without the jargon

Plus: Doug’s trivia takes a nostalgic turn into the wild world of Beanie Babies

FULL SHOW NOTES: https://stackingbenjamins.com/how-not-to-invest-1660

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.

How Pros Build Motivation Into an Effective Financial Plan (SB1659) Mar 21, 2025

Show notes

Ever wonder why some people crush their financial goals while others keep hitting snooze? Today, we’re talking about the secret sauce behind sticking to a financial plan—and no, it’s not just “wanting it more” (though that helps). Joining Joe in the basement is OG, alongside personal finance expert Jesse Kramer from The Best Interest and CFP Dana Anspach from Sensible Money. Together, they’ll break down why staying financially motivated is harder than it looks—and how to actually keep yourself on track, even when life (or a killer sale on Amazon) tries to derail you.

We’ll explore why people resist financial planning (hint: it’s not always laziness), how goal-setting psychology plays into money habits, and why tracking your finances can be as powerful as tracking your fitness. Dana shares the surprising link between logging your retirement balance and saving more, while OG and Jesse tackle the age-old debate: should financial advisors be more like sports agents—pushing, coaching, and sometimes delivering the tough love? Plus, we dig into why writing things down actually works (seriously, it’s science) and how a simple mindset shift can help you finally take action.

And of course, what’s a Friday without Doug’s trivia? This week, Doug takes us back to the boxing ring with a question about the legendary Joe Louis—and the sucker punch that is junk fees. ? Our roundtable throws their best guesses into the ring, but who will come out on top? Play along and see if you can take home the trivia belt!

This was a great finish to a week of talking motivation and drive! From the seven steps to dynamic drive to sports agent Molly Fletcher on Wednesday and this discussion, it's a well-rounded week that should help you get up and go...even if you think YOUR get up and go got up and went.

FULL SHOW NOTES: https://stackingbenjamins.com/motivation-habits-and-planning-1659

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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Climb Out of Your Rut: Molly Fletcher on Creating Sustainable Motivation (SB1658) Mar 19, 2025

Show notes

Ever feel like you're stuck in a rut, spinning your wheels, or just running low on motivation? Today, we crack the code on sustaining drive and avoiding complacency with former sports agent Molly Fletcher, who’s worked with some of the biggest names in sports and has been dubbed the female Jerry Maguire. She breaks down the fine line between contentment and coasting, plus shares keys to staying at the top of your game—from managing energy to embracing adversity like a pro.

But wait, there’s more! Len Penzo (yes, of LenPenzo dot com fame!) joins us as guest co-host, bringing his usual mix of wisdom, dry wit, and probably a few thoughts on sandwich prices.

And if you think motivation is tough, try navigating the world of credit—because while ambition is great, bad credit can still trip you up. From student loan pitfalls to practical credit repair tips, we cover what younger folks (and honestly, all of us) need to know about keeping those numbers in check.

In this episode:

Molly Fletcher on Peak Performance – Lessons from a top sports agent on how to stay motivated without burning out.

Complacency vs. Contentment – Are you stuck or simply satisfied? Molly breaks it down.

Managing Energy Like a Pro – Tom Izzo swears by it, and so should you.

Credit Crash Course – What happens when student loans go delinquent, and how to fix the damage.

The Living Without Credit Debate – Is a debt-free life possible, or just a financial myth?

Doug & OG’s Ski Slope Disaster – A story of poor decisions, gravity, and bruised egos (hilarious in retrospect).

Len Penzo's Tips for Improving Credit Scores – Because nobody budgets quite like Len.

Whether you need a motivation boost, a credit check-up, or just a good laugh at Doug’s expense, this episode has you covered.

🎧 Tune in for wisdom, financial hacks, and some après-ski storytelling you won’t want to miss!

FULL SHOW NOTES: https://www.stackingbenjamins.com/find-your-dynamic-drive-molly-fletcher-1658/

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 Use Process to Create Sustainable Drive (SB1657) Mar 17, 2025

Show notes

Ever start a new financial goal feeling unstoppable, only to lose momentum when life gets in the way? Staying motivated isn’t just about working harder—it’s about working smarter.

Today, Joe and OG take a deep dive into Dynamic Drive, the key to keeping your financial momentum going without burnout. We’ll break down the seven essential pillars—mindset, energy, discipline, curiosity, resilience, connection, and confidence—so you’re ready to hit the ground running when we welcome former sports agent Molly Fletcher on Wednesday.

💰 In this episode:

Why motivation fizzles out—and how to make it last

The seven keys to Dynamic Drive (and how to apply them to your finances)

How milestones and energy management keep you on track

Tax strategies for selling shares—FIFO, LIFO, or average cost? Which method helps you keep more of your hard-earned Benjamins?

What cowboy fencing teaches us about peak performance (yes, that’s a thing)

Plus, Doug serves up a sports trivia challenge—because what’s financial motivation without a little fun?

👉 Listen in now and get fired up—without burning out!

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-create-a-sustainable-drive-1657

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.

Yeah, We Overpaid for That (SB1656) Mar 14, 2025

Show notes

Ever feel guilty about that $7 airport coffee or the mystery fees that somehow turn your $15 DoorDash order into a $40 financial regret? You’re not alone. This episode, Joe Saul-Sehy is joined by Paula Pant (Afford Anything) and Justin Peters (The Struggle Is Real) to unravel the sneaky ways convenience drains our wallets.

In this episode:

Airport Food: The Ultimate Financial Heist – Why does a sad turkey sandwich cost more than a steak dinner? We investigate.
Concert Tickets & Junk Fees – You found $50 tickets… but somehow the total is now $127? Yep, we’ve been there.
The True Cost of Convenience – From Uber Eats to express shipping, when is paying extra worth it—and when are we just being lazy?
Trivia Time: Pie Day Special! – Who knew McDonald's pie sales could spark heated debate? Well, now we all do.
Wedding Costs Gone Wild – Creative ways to cut costs without making your guests eat ramen.
The Ben Franklin Effect & Social Hacks – Want better connections without breaking the bank? Turns out, old Ben had some wisdom on that, too.

All this, plus some hilarious personal finance confessions that will make you feel better about your last impulse buy.

🎧 Tune in, laugh, and learn how to keep more of your Benjamins!

FULL SHOW NOTES: https://stackingbenjamins.com/places-we-know-were-overpaying-1656

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 Best Tax Prep Software of 2025 (SB1655) Mar 12, 2025

Show notes

Choosing the Best Tax Software for Your Needs

Tax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you're a side hustler, crypto investor, or just looking for a free filing solution.

Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by which software stands out this year.

H&R Block’s virtual tax prep – If you want real humans to double-check your numbers, this might be your go-to.

Which tax software works best for unique situations – Side gigs, stock trading, crypto investments… different situations call for different solutions.

Navigating Tax Day without the stress – Tips to avoid last-minute panic and make sure you’re not leaving money on the table.

Crypto scams and meme coins – Because tax season isn’t stressful enough without adding that mess into the mix.

Meanwhile, Doug serves up world-famous trivia with a nod to classic children’s books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, and—of course—movie recommendations.

If tax season feels overwhelming, this episode breaks it down, keeps it light, and helps you pick the right software to file with confidence.

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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Dream Big, Live Free: Grant Sabatier's Guide to Entrepreneurship (SB1654) Mar 10, 2025

Show notes

Ever wondered if working for yourself could be the game-changer your finances need? Grant Sabatier thinks so, and today, he’s diving into the realities of entrepreneurship—from smart strategies to potential pitfalls.

Where to start if you’re considering entrepreneurship – Not every side hustle is a winner, so how do you know if this path is right for you?
The power of systems and constraints – Why guardrails and structure matter more than unlimited freedom.
Pricing strategies and finding customers – Because even the best ideas need paying customers.
Entrepreneurial misconceptions – Spoiler: It’s not all Ferraris and private jets.
Can your wedding be a tax deduction? – We explore the entertaining but highly questionable ways some people try to make this work.

Meanwhile, Doug serves up trivia on the highest-grossing console game ever (bet you won’t guess it). And if you stick around long enough, let’s just say there may or may not be a discussion about a comedy movie that turns financial struggles into pure entertainment. But, you know… no promises.

If you’ve been toying with the idea of starting your own thing, this episode is packed with insights, real talk, and a few surprises along the way.

FULL SHOW NOTES: https://stackingbenjamins.com/unlock-your-inner-entrepreneur-with-grant-sabatier-1654

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

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The Surprising Benefits of Financial Inaction (SB1653) Mar 07, 2025

Show notes

Feeling the pressure to constantly tweak your investments? Today, we uncover the surprising benefits of financial inaction with insights from CFP Dana Anspach, Len Penzo, and OG. We dive into the wisdom of sometimes doing nothing—because, as it turns out, sitting on your hands (financially speaking) can be a power move.

Why lazy portfolio management might be the smartest strategy you’ll ever adopt (spoiler: it involves less work).
The power of downtime—turns out, stepping away from your money might actually make you richer.
Why your future self will thank you for setting up auto-pay (hint: fewer late fees, more naps).
The sneaky ways peer pressure messes with your finances—and how to keep the Joneses from running your budget.
When rebalancing your portfolio is necessary…and when it’s just a fancy way to micromanage yourself.
A wildly unexpected insurance claim (because finances are never boring in the basement).

Oh, and Doug’s got a trivia question about a particularly controversial activity that was banned—because, apparently, not everything fun is legal.

Stick around for weekend plans, final thoughts, and maybe even a surprise or two (because we like to keep you on your toes).

This episode originally aired on June 10, 2022. Please disregard any mention of current events.

The original show notes can be found here.

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.

Our Top 5 Favorite Parts of a Well-Crafted Financial Plan SB1652 Mar 05, 2025

Show notes

A great financial plan isn’t just about numbers—it’s about creating a roadmap that turns dreams into reality. Today, Joe and OG take a trip down memory lane, reflecting on their favorite parts of building a great financial plan. Whether you're tackling long-term goals, fine-tuning your tax strategy, or simplifying complex decisions, they’ll walk you through the key elements that turn financial chaos into a well-oiled machine.

Breaking down big goals into bite-sized wins – Because climbing a financial mountain is easier when you focus on one step at a time.
The magic of tax strategies – Why a little planning now can keep more Benjamins in your pocket later.
Risk management done right – Avoiding financial pitfalls so your plan stays strong, no matter what life throws your way.
The power of simple solutions – Complexity doesn’t always mean better. Sometimes, the best financial strategies are the easiest to execute.
The role of a financial guide – Whether you DIY your plan or bring in an expert, knowing when to get guidance is a game-changer.

Meanwhile, Doug tackles a ‘Winnie the Pooh’-inspired predicament (honey jars may or may not be involved) and drops some surprising trivia on the massive market value of antidepressant drugs.

If you’re ready to streamline your financial life and celebrate your progress along the way, this episode is packed with insights, strategy, and a few unexpected twists.

This episode originally aired on January 18, 2023. Please disregard any mention of current events.

The original show notes can be found here.

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.