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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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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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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What’s the best way to save for a house without wrecking your retirement plan? That’s just one of the big questions Joe Saul-Sehy, OG, and Mom’s neighbor Doug tackle in this packed episode (number 1700!) of Stacking Benjamins. Whether you're trying to figure out where to park your emergency fund, how to handle inherited IRAs, or how to financially plan as a single adult with big responsibilities (hello, aging parents!), this episode is full of relatable scenarios and actionable strategies.

Stackers Torin, VJ, Lori, and Michelle ask everything from:

How much is too much in your emergency fund?

What happens to inherited IRAs when you're already juggling financial priorities?

What should single people be doing right now to prepare for the future?

How do you juggle helping aging parents while keeping your own goals on track?

Plus, we mix in commentary from Kevin at Edward Jones and longtime listener Ron—offering insights from inside the financial services world and the Stacker community. The guys debate personal finance media narratives, give practical advice for budgeting large windfalls, and reflect on why saving feels easier in theory than in practice.

Also covered in this episode:

Why financial advice often skips over single individuals—and what to do about it

Emergency fund strategies: where to park the money, how much to keep, and how to make peace with the fact it isn’t earning sky-high returns

How to prioritize debt, student loans, savings, and investing without setting off a financial anxiety spiral

The value of short-term tradeoffs when you’ve got long-term goals

All delivered with the basement’s signature charm—where the coffee is lukewarm, the guidance is practical, and the jokes… well, let’s just say they’re dividend-eligible.

This episode is a perfect listen for:

New Stackers building their financial foundation

DIYers trying to juggle competing money goals

Anyone who’s inherited assets and doesn’t want to mess it up

People who’ve realized adulting is basically managing 14 financial priorities at once and still remembering to bring snacks.

FULL SHOW NOTES: https://stackingbenjamins.com/answering-your-questions-mailbag-1700

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 robots aren’t just coming—they’re already here. And if you’re not paying attention, they might not just take your job… they could take your personal data too. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Doug dive into the rise of artificial intelligence, exploring whether it’s a threat, a tool, or something in between. If you’ve been wondering how AI will impact your work, your privacy, and your future, this episode is a must-listen.

They kick off with a surprising headline: Gen Z workers are sidestepping AI entirely—not by resisting it, but by choosing careers where machines can’t compete (like landscaping and trades), and using AI tools to grow their businesses faster. This sparks a full-on basement debate about how technology has historically impacted jobs, what the next evolution might look like, and whether AI will make our lives easier… or just busier.

In today’s show:

Why some jobs may disappear—but others are about to explode with opportunity

The surprising role AI is playing in blue-collar and skilled trade growth

Why being AI-curious (not AI-phobic) is your best financial move

New tech tools that supercharge productivity—from transcription wallets to note-taking bots

How AI is already transforming education and career paths

What to do right now to stay ahead of the AI curve

Then the guys shift gears to a more sinister topic: data privacy. CNET recently reported which free AI chatbots are scooping up the most of your personal info—and which are surprisingly respectful. The gang reveals which apps are best to trust, and which are like letting Zuck crash on your couch (bad idea).

We’ll also hear from listener John, who wants to hire a financial advisor but isn’t sure where to start. Joe and OG break down how to find the right fit, why fees aren’t the most important factor, and the one question that tells you if someone’s worth hiring.

Plus:

Doug’s trivia on egomaniacal coin designers

A TikTok minute about U2, dating apps, and dad jokes

Back porch chatter about Pontiac Azteks, water treatment careers, and IMAX concert pilgrimages

Takeaway: AI isn’t just a tech trend—it’s reshaping our economy, our careers, and even how we learn. Whether you’re a Gen Z worker, mid-career professional, or planning your retirement, now’s the time to lean in, explore what AI can (and can’t) do, and secure your future before the bots beat you to it.

FULL SHOW NOTES: https://stackingbenjamins.com/ais-coming-for-your-job-how-to-outwit-the-robots-1699

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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So you’ve scaled the mountain, built the nest egg, and maybe even shouted “I’m done!” across a pristine beach... now what?

In today’s Stacking Benjamins episode, Joe Saul-Sehy convenes a roundtable of heavy-hitters to tackle the most misunderstood phase of money management: decumulation—a.k.a. the art of spending what you’ve worked so hard to save. Whether you're staring down retirement or already deep into your golden years, you'll hear candid, practical insights from three financial thought leaders who specialize in making your money last.

Joining Joe are Dana Anspach, retirement planning expert and founder of Sensible Money, Karsten Jeske (aka “Big ERN” from Early Retirement Now), and Frank Vasquez, aka Uncle Frank, host of Risk Parity Radio. Together, they bring decades of academic research, professional experience, and plain old common sense to questions like:

What’s the real safe withdrawal rate—and why does it depend on more than just spreadsheets?

Should you chase simplicity or embrace complexity in managing retirement funds?

What role do annuities and guaranteed income play in reducing late-life anxiety?

How do you plan for cognitive decline without spiraling into existential dread?

What’s the difference between spending confidently... and spending carelessly?

You’ll also hear why lumpy expenses, long-term care surprises, and behavioral quirks can trip up even the best-laid plans—and how to bulletproof your strategy now.

And yes, we get nerdy. Risk parity, sequence of return risk, and portfolio glidepaths all make guest appearances—but always with your favorite Stacking Benjamins charm and plain-English style. Because retirement doesn’t need to be scary... but it does need to be intentional.

Why your investment approach needs to evolve once paychecks stop

The strengths and blind spots of the “4% rule”

How emotions (not just inflation) affect safe withdrawal strategies

When it makes sense to annuitize, and when it absolutely doesn’t

How to adjust for cognitive decline in your financial plan (and still maintain autonomy)

The “spend conservatively early” myth—debunked

Tips for managing healthcare and other unpredictable late-life costs

Whether you’re a retiree, a pre-retiree, or a spreadsheet-loving financial independence buff, this deep-dive episode will give you the confidence to manage the second half of your financial life like a pro.

This isn't just about stretching your dollars—it's about building a life worth spending them on.

So grab your planner, pour a cup of whatever says “retirement-ready” to you, and let’s get smarter (and maybe just a bit weirder) about your golden years.

FULL SHOW NOTES: https://stackingbenjamins.com/create-your-retirement-spending-plan-1698

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 if the most important part of your retirement plan had nothing to do with your 401(k), IRA, or stock portfolio? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by filmmakers Pete Davis and Rebecca Davis, creators of the thought-provoking documentary Join or Die. They explore how community connection, not cash, may be the ultimate retirement strategy.

Drawing inspiration from the late political scientist Robert Putnam (Bowling Alone), the Davises reveal why joining groups—book clubs, church choirs, rec leagues, neighborhood associations—might be more essential to your long-term well-being than your asset allocation.

Together with Joe and OG, they unpack the data behind social decline, the healing power of showing up, and what the film Join or Die teaches us about leading a richer life beyond the numbers. Of course, Mom’s Neighbor Doug pops in with trivia that proves he belongs (at least to this show).

Whether you’re on the path to retirement or simply looking for deeper purpose, this episode will make you think differently about how you stack your most valuable resource: time.

Why joining a club may be just as critical to retirement as saving for it

What Join or Die reveals about America’s shrinking social networks

How loneliness affects physical and financial health—and how to fight it

Why your “portfolio of community” might be the highest-yield investment you ever make

Ways to build meaningful connections now—even if you don’t feel like a “joiner”

Pete and Rebecca Davis share behind-the-scenes stories from making Join or Die

Joe and OG reflect on what gives life meaning after the 9-to-5 ends

Surprising data on the link between social capital and financial confidence

Doug delivers a trivia challenge about famous clubs (and less-famous neighbors)

📚 Resources & Mentions:

🎥 Join or Die documentary by Pete and Rebecca Davis

📘 Bowling Alone by Robert Putnam

🎙️ Pete Davis’s book: Dedicated: The Case for Commitment in an Age of Infinite Browsing

👟 Your Challenge This Week:

💬 “Retirement planning isn’t just about money—it’s about meaning.”

FULL SHOW NOTES: https:;//stackingbenjamins.com/join-or-die-documentary-pete-rebecca-davis-1697

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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You can’t plan a great retirement if you haven’t first planned what you’re retiring to. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug open up Retirement Week in the basement with a Monday that’s equal parts insight, weekend recap, and questionable vehicle decisions.

🚪 Start with the most overlooked part of retirement: your lifestyle vision. What are you actually going to do all day—and will it make you happy?

📊 Then they dive into financial strategy, from coordinating pre-tax, Roth, and taxable funds to dodging sneaky IRMAA fees that show up like glitter—impossible to get rid of and oddly expensive.

🏎️ Thinking about a new car? Joe and Doug wrestle with the age-old question: maintain or upgrade, and how your answer could affect your wallet (and maybe your driveway credibility).

💼 Curious about investment leverage? Meet Basic Capital—a platform that might sound like a good idea… until it doesn’t. Joe and OG explain when leverage can help—and when it’s just risk in a tuxedo.

🎧 Plus:

Saluting the troops

What not to do when your retirement plan involves TikTok

A sneak peek at the Nerdy Round Table

And entertainment recs to round out your week like a pro

Start your week smarter and get a little closer to a retirement you actually want.

FULL SHOW NOTES: https://stackingbenjamins.com/creating-a-better-retirement-1696

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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Markets crashing? Interest rates spiking? Inflation roaring? Welcome to history. This week, we dig into 130 years of stock market meltdowns—from the panic of World War I to the Great Depression, 1970s stagflation, the dot-com collapse, and the 2008 financial crisis—to uncover timeless lessons that can fortify your financial future.

Joe Saul-Sehy is joined by Miranda Marquit, Jesse Cramer, and OG to examine how investors have historically responded to chaos... and how you should, too. You'll learn why diversification matters, why panic rarely pays, and why staying the course (even when it’s scary) can be the smartest move of all.

Of course, this wouldn't be the Stacking Benjamins Show without a trivia detour that involves mailing children through the U.S. Postal Service (yes, that happened). Buckle up for laughter, insight, and financial takeaways that are as practical as they are entertaining.

What WWI, the Great Depression, and 1970s inflation can teach us about investing

Why “The Lost Decade” wasn’t a loss for long-term thinkers

How to build a resilient portfolio that weathers the storm

Our infamous trivia game: How much could a kid weigh and still be legally mailed in the 1920s?

A few money-saving hacks, podcast updates, and your weekend preview from the basement

Whether you’re a seasoned investor or just building your financial foundation, this episode will leave you smarter, more confident, and—let’s be honest—way more amused than the average market history lecture.

FULL SHOW NOTES: https://stackingbenjamins.com/lessons-from-stock-market-history-1695

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 happens when you mix financial strategy with a healthy dose of cultural commentary? You get Rich Girl Nation. This week on The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Katie Gatti Tassin, the powerhouse behind Money with Katie and author of the new book Rich Girl Nation. Together, they unravel the sneaky ways consumerism shows up in our lives—from pricey trends to status-signaling spending—and how it messes with our wallets.

Katie dives into the “hot girl hamster wheel” of overspending, the wage gap, and why negotiating your salary (without flinching) is one of the best financial moves you can make. She also offers sharp, tactical advice on job-hopping for higher pay and automating your money to avoid lifestyle creep. Meanwhile, the crew throws in real-life stories, from Cybertruck depreciation to celebrating financial independence in more ways than one.

And of course, Doug drops in with a trivia twist that keeps things weird—because it wouldn’t be the basement without a little curveball.

🧠 What You’ll Learn:

Whether you're climbing the corporate ladder or just trying to spend smarter, this episode offers a refreshing mix of real talk and practical advice—served up with classic basement wit and a side of financial independence.

Let’s make money moves that actually feel good.

FULL SHOW NOTES: https://stackingbenjamins.com/rethinking-earning-and-spending-with-kate-gatti-tassin-1694

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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