The Stacking Benjamins Show

Latest Episodes:

Jonathan Clements: Why Simple Beats Complicated Every Time (SB1760) Nov 12, 2025

Show notes

Here's what nobody tells you about building wealth: it's not about finding the perfect investment or timing the market. It's about doing boring things consistently until they're not boring anymore—they're just your life.

In this Greatest Hits episode, Joe Saul-Sehy and OG revisit a 2023 conversation with Jonathan Clements, the beloved former Wall Street Journal personal finance columnist and founder of Humble Dollar who passed away recently. We're resharing this episode to honor Jonathan's legacy, his gift for making complex ideas simple, and the joy he brought to every conversation about money.

Jonathan's book, My Money Journey, features 30 real stories from real people who built financial freedom—and the lessons are surprisingly simple (which doesn't mean easy). In this conversation, Jonathan breaks down what separated the people who made it from the people who kept spinning their wheels: steady habits, ruthless simplicity, and the kind of resilience that lets you keep going when life throws curveballs.

From emergency funds that actually saved people to the rent vs. buy debate that reveals more about your priorities than your budget, this conversation cuts through the complexity to show you what actually matters. Jonathan's wisdom feels even more valuable now—a reminder that the best financial advice isn't about chasing trends, it's about building a life that works for you.

Joe and OG also tackle listener questions, including whether to relocate for a better job and how to balance saving for tomorrow without sacrificing today. Plus: Doug's trivia, a Key & Peele-inspired TikTok minute, and proof that the best financial teachers leave lessons that last long after they're gone.

What You'll Walk Away With:

• The money habits that showed up in almost every success story from Jonathan's book (spoiler: none of them are sexy)

• Why simplicity beats complexity in investing—and how to stop overcomplicating your portfolio

• The rent vs. buy question reframed: it's not just about math, it's about what kind of life you want

• How to balance aggressive investing with the safety net you actually need (not the one Instagram tells you to have)

• Why emergency funds and health insurance are the unsexy heroes of every financial success story

• What "margin for error" really means—and why it's the difference between surviving setbacks and being destroyed by them

This Episode Is For You If:

• You're tired of chasing the next "hot" investment strategy and want to know what actually works

• You feel like everyone else has figured out money except you (spoiler: they haven't)

• You want to hear real stories from real people, not just theory from talking heads

• You're trying to balance living well now with saving for later—and feeling stuck in the middle

• You believe the best teachers are the ones whose lessons outlive them

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 a 12-Hour Walk Teaches You About Money (And Life) SB1759 Nov 10, 2025

Show notes

Here's a wild idea: What if the thing holding you back isn't your bank account, your age, or your circumstances—it's just the story you've been telling yourself?

Joe Saul-Sehy and OG sit down with Colin O'Brady, four-time world record holder and endurance athlete who's done things most people would call impossible: solo trek across Antarctica, row across the Drake Passage, and yes, take a 12-hour walk that changed his entire perspective on what humans are capable of.

Colin's not just here to tell adventure stories (though those are incredible). He's here to talk about the mental game—the part where you convince yourself to take the first step even when the finish line seems impossibly far away. Sound familiar? Whether you're staring down a cross-country expedition or trying to figure out if you'll have enough saved for retirement, the challenge is the same: push past the voice that says "I can't" and prove to yourself that you can.

Then Joe and OG bring it back to the basement with a listener question about Roth vs. Traditional 401(k) contributions—because financial endurance is just as important as physical stamina. They break down how to think long-term about taxes, flexibility, and building a retirement plan that actually fits your life.

Plus: Neighbor Doug delivers trivia that proves even world record holders have to earn their laughs in the basement.

What You'll Walk Away With:

• What Colin O'Brady's 12-Hour Walk reveals about breaking through your mental limits (and how it applies to money decisions too)

• The mindset shift that separates people who attempt big goals from people who actually achieve them

• Smart strategies for balancing Roth and Traditional 401(k) contributions based on your timeline and tax situation

• Why flexibility matters as much as discipline—whether you're planning an expedition or planning retirement

• Permission to set goals that scare you a little (because that's usually where the good stuff happens)

This Episode Is For You If:

• You've been telling yourself you "can't" do something but wonder if that's actually true

• You want inspiration that comes with actual tactics (not just motivational fluff)

• You're trying to figure out the Roth vs. Traditional 401(k) question and want a clear answer

• You believe your best life is out there, but you're not sure how to build toward it

• You need a reminder that big transformations start with small, intentional steps

FULL SHOW NOTES: https://stackingbenjamins.com/conquer-your-mount-everest-greatest-hits-week-1759

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 Retirees Wish They'd Known 10 Years Ago (SB1758) Nov 07, 2025

Show notes

Want to know what keeps retirees up at night? It's not what they did—it's what they wish they'd done ten years earlier.

Joe Saul-Sehy is joined by Jill Siriani (Frugal Friends), Jesse Cramer (The Best Interest), and Doc G (Earn & Invest), who all pull up chairs in the basement for a powerhouse roundtable on the five regrets that show up again and again when people hit retirement. These aren't hypothetical "what-ifs"—they're real stories from a real CFP, sharing tales about people who wished someone had told them sooner.

From botched investment allocations that left people either too risky or too conservative, to tax mistakes that cost tens of thousands, to the heartbreaking pattern of people who saved everything but never actually enjoyed their money—this conversation gets real about what actually matters when you're trying to retire with confidence (and joy).

The good news? Every single one of these regrets is avoidable. The panelists share what to do now so you don't become one of these stories later, including the estate planning moves that take ten minutes but save your family years of headaches, and why the biggest retirement regret isn't financial at all—it's emotional.

Plus: Doug's trivia challenge pits the panel against each other for bragging rights, because even serious money talk deserves a little competition.

What You'll Walk Away With:

• The five regrets that show up over and over in retirement—and the specific moves that prevent each one

• Why your investment allocation in your 40s and 50s might be setting you up for regret in your 60s

• Tax strategies that keep more money in your pocket (because giving Uncle Sam extra is nobody's retirement dream)

• The simple estate planning steps most people skip—and why your family will thank you for not skipping them

• How to give yourself permission to actually enjoy your money instead of hoarding it out of fear

This Episode Is For You If:

• You're decades from retirement but want to avoid the "I wish I'd known" moments

• You're closer to retirement and worried you've missed something important

• You want to hear top financial minds debate what actually matters (spoiler: they don't always agree)

• You're tired of generic retirement advice and want to hear what real retirees actually regret

• You believe retirement should be about living well, not just having enough

FULL SHOW NOTES: https://stackingbenjamins.com/top-5-retirement-plan-regrets-1758

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.

Financial Literacy for Kids + Are Annuities Actually Safe? SB1757 Nov 05, 2025

Show notes

Here's a question: If everyone's buying annuities right now, does that mean you should too?

Joe Saul-Sehy, OG, and Neighbor Doug tackle that exact question in this week's episode—but first, they're starting with the basics. Because before you can figure out complex financial products, you need to nail the fundamentals. And who better to teach them than Karen Holland, founder of Gifting Sense, who's made it her mission to help kids (and their parents) understand money in ways that actually stick.

Karen breaks down how to teach the next generation about "need vs. want," why middle schoolers need to understand the real cost of "cool," and how financial literacy can be empowering instead of intimidating. Whether you've got kids or just want a refresher on the money basics you wish someone had taught you, this conversation is the reset button you didn't know you needed.

Then things get timely: annuity sales are booming, and everyone's suddenly got an opinion. But are annuities the safe harbor they're marketed as, or just another way to lock up your money with fees you don't understand? Joe and OG cut through the sales pitch to help you figure out when annuities make sense—and when you're better off walking away.

Plus: Doug delivers "life-changing" trivia (his words), there's an iHeart Music Festival giveaway tied to financial literacy, and you'll get your weekly dose of basement wisdom served with laughs.

What You'll Walk Away With:

• Karen Holland's framework for teaching kids financial literacy that actually changes behavior (not just lectures that go in one ear and out the other)

• Why annuity sales are exploding right now—and the questions you MUST ask before signing anything

• The difference between annuities that solve real problems and annuities that just create expensive ones

• Financial habits that work at any age—whether you're teaching a 12-year-old or retraining yourself

• How supporting financial education can score you iHeart Music Festival tickets (because doing good shouldn't be boring)

This Episode Is For You If:

• You want to teach kids about money but don't know where to start (or worry you'll mess it up)

• Someone's pitched you an annuity and you're not sure if it's brilliant or a trap

• You've heard annuities are "safe" but want to understand what you're actually giving up

• You believe financial literacy is a gift worth giving—to your kids, your community, or yourself

• You want money advice that doesn't talk down to you or assume you already know everything

FULL SHOW NOTES: https://stackingbenjamins.com/raising-money-for-financial-literacy-1757

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.

What to Do When Money Gets Tight SB1756 Nov 03, 2025

Show notes

Nobody plans for their finances to get tight. But here you are, staring at your bank account, wondering if you should panic now or wait until next Tuesday.

Joe Saul-Sehy, OG, and Neighbor Doug are here to talk you off the ledge—and give you an actual plan for when money gets squeezed. Whether you're facing a layoff, dealing with reduced hours, bracing through a government shutdown, or just trying to make your paycheck last until payday, this episode is your financial storm shelter.

The good news? You don't need to have everything figured out perfectly to make it through. You just need to know what to do first, what can wait, and how to keep your head (and your budget) together when everything feels uncertain. From building an emergency fund that actually works for your life to eating well on a ramen budget (spoiler: it's possible), this crew breaks down the practical moves that keep you afloat.

Plus: Doug delivers trivia, the gang tackles the Voices for Good Charity Challenge (because even in tough times, small acts of giving matter), and they dissect a TikTok money tip that's... well, let's just say not all financial advice should be followed.

What You'll Walk Away With:

• The first three moves to make when money gets tight—before the panic spiral starts

• How much emergency fund you actually need (hint: it's probably less than you think to get started)

• Budget-friendly tactics for groceries, utilities, and keeping yourself fed without living on instant noodles

• What to do about insurance and loans when cash flow slows down (and which mistakes cost you later)

• Why small acts of generosity matter even when you're struggling—and how they help you too

• A reminder that financial storms are temporary, but the skills you build weathering them last forever

This Episode Is For You If:

• Money feels tighter than it used to and you're not sure what to do about it

• You want to build a safety net but don't know where to start (or how much is "enough")

• The economy feels shaky and you want to feel prepared instead of panicked

• You're tired of generic advice like "just save more" and want actual tactics

• You need a pep talk wrapped in practical wisdom—because optimism without a plan isn't helpful

FULL SHOW NOTES: https://stackingbenjamins.com/the-importance-of-emergency-funds-1756

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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Tales of Financial Horror (and how we exorcised them) SB1755 Oct 31, 2025

Show notes

Pop quiz: What's scarier than a haunted house? Opening your credit card statement after a "just this once" shopping spree turned into a six-month spiral.

Joe Saul-Sehy and Neighbor Doug gather 'round the basement campfire with Doc G (Jordan Grumet from Earn and Invest), Jesse Cramer (Personal Finance for Long Term Investors), and special guest Emily Egashira—AKA Your Friend Em from TikTok and Instagram fame—to share the financial horror stories that still wake them up at night. We're talking ghostly car-leasing nightmares, investment decisions that refuse to stay buried, and the kind of money mistakes that haunt you long after Halloween is over.

But here's the thing about financial horror stories: they're only scary if you don't learn from them. Every tale in this episode comes with the lesson that could've prevented it—the red flag that got ignored, the advice that should've been followed, the moment when "this seems like a bad idea" got drowned out by "but everyone else is doing it."

From impulse purchases that turned into long-term regrets to the financial advice that sounded great... until it didn't, this crew proves that the scariest monsters aren't in the movies. They're in our bank accounts, our retirement plans, and that subscription we forgot to cancel three years ago.

Plus: Doug delivers Halloween trivia with a full-moon twist, because even financial terror deserves a side of fun.

What You'll Walk Away With:

• Real financial horror stories from people who lived to tell the tale (and learn from it)

• The common thread in most money disasters—and how to spot it in your own life

• Why car leases, "great investment opportunities," and "everyone's doing it" should always make you pause

• How to turn your own financial frights into lessons instead of letting them haunt you forever

• The confidence to say "no" when something feels off, even if you can't explain why

This Episode Is For You If:

• You've ever made a money decision you immediately regretted (welcome to the club)

• You want to learn from other people's expensive mistakes instead of repeating them

• You've got a financial skeleton in your closet and need to know you're not the only one

• You appreciate brutal honesty wrapped in humor—because laughing at financial pain is cheaper than therapy

• You're ready to face your money fears instead of hiding from them until tax season

FULL SHOW NOTES: https://stackingbenjamins.com/money-nightmares-wallet-portfolio-credit-1755

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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Banishing Money Monsters: How to Talk Money With Anyone (Partners, Roommates, or Coworkers) SB1754 Oct 29, 2025

Show notes

You know what's truly terrifying? Realizing you and someone you share money decisions with have completely different ideas about finances—and you're both convinced you're right.

Joe Saul-Sehy and OG welcome Doug and Heather Bonaparte, a CFP and business partner duo who've mastered the art of not killing each other over finances. And when you work together AND live together? Let's just say they've had plenty of practice navigating the financial frights that haunt any relationship where money's involved.

Whether you're married, dating, splitting rent with a roommate, or partnering on a business venture, the same money monsters show up: the "fair split" debates, the family expectation zombies that won't stay dead, and those vampiric spending habits that drain shared accounts when you're not looking. Doug and Heather share what actually works—the timing tricks, the tone shifts, and the teamwork strategies that keep financial conversations from turning into horror shows, no matter who you're talking to.

This isn't about becoming perfect financial partners overnight. It's about exorcising the money demons before they possess your most important relationships—romantic, professional, or otherwise.

Plus: Joe and OG stir the cauldron with Halloween movie talk and trivia, because even the scariest conversations are better with a little basement humor.

What You'll Walk Away With:

How to start money conversations without summoning the spirits of past arguments (works for spouses, roommates, business partners, you name it)
Doug and Heather's hard-won strategies for navigating disagreements when money and relationships overlap
Why "financial transparency" isn't about policing every purchase—it's about understanding each other's money ghosts
The three things any financial partnership needs to align on before the little stuff stops haunting you
Permission to be messy while you figure this out (even CFPs have money fights)

This Episode Is For You If:

You share financial decisions with ANYONE—a partner, roommate, business associate, or family member
Money conversations feel like walking through a haunted house blindfolded
Someone else's financial habits make you want to scream louder than a horror movie victim
You're tired of being cast as the villain every time you want to discuss shared expenses
You need proof that even professionals who literally do this for a living still have to work at it

FULL SHOW NOTES: https://stackingbenjamins.com/money-communication-horror-stories-1754

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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Real Money Horror Stories (And How Not to Star in Your Own) SB1753 Oct 27, 2025

Show notes

What's scarier than a haunted house? Looking at your retirement account after ignoring it for five years.

Joe Saul-Sehy, OG, and Doug welcome back Chuck Jaffe (Money Life with Chuck Jaffe) for his legendary annual Halloween visit—and this year, he's bringing two treats to the basement.

First up: Chuck's Halloween Money Game for kids. Picture this: trick-or-treaters can take one piece of candy and walk away... or they can play a game where they might win more candy, actual money, or lose it all. It's economics wrapped in a Snickers bar. Chuck breaks down how each choice teaches kids (and parents) about risk, reward, delayed gratification, and why sometimes the safe bet is actually the smart bet. If you've got kids—or just want a genius way to gamify money lessons—you'll want to steal this.

Then things get spooky. Real Stackers share their most bone-chilling financial horror stories: the credit union error that nearly cost someone their house, the coworker's "advice" that turned into a disaster, and the procrastination that haunted someone for years. These aren't fictional frights—they're real mistakes that real people are still recovering from. And every story comes with the lesson that could've prevented it.

Plus: Doug's trivia takes a Halloween turn (naturally), and Joe and OG debate whether government incentives are more trick or treat.

What You'll Walk Away With:

Chuck Jaffe's brilliant Halloween Money Game—how to teach kids about risk, reward, and smart decisions using candy
The economic principles hiding in every trick-or-treat choice (and how to explain them without killing the fun)
Real Stacker horror stories: the financial mistakes that haunt people for years
The red flags that could save you from starring in your own money nightmare
Why the scariest financial advice often comes from people who mean well

This Episode Is For You If:

You want a creative way to teach kids about money that doesn't involve a boring lecture
You've ever made a financial decision you wish you could take back
You want to learn from other people's mistakes instead of making them all yourself
You've got a money skeleton in your closet and want to know you're not the only one

FULL SHOW NOTES: https://stackingbenjamins.com/frightening-halloween-stories-with-chuck-jaffe-1753

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.

You've Got Enough Money to Quit. Should You? SB1752 Oct 24, 2025

Show notes

Here's a question nobody in the FIRE movement talks about: What if you reach financial independence... and don't want to quit?

Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Doc G (Earn & Invest) tackle the idea of Reverse FIRE—people who've hit their number but choose to keep working anyway. And before you roll your eyes, hear them out.

Because it turns out that having enough money doesn't automatically make you happy. And for a lot of people, walking away from work means walking away from purpose, identity, and the structure that kept them sane. The question isn't just "can I afford to retire?"—it's "what am I retiring to?"

This conversation gets real about the hidden costs of quitting too soon, why some financially independent people feel guilty for wanting to work, and how to think about retirement not as a finish line but as a design problem. Whether you're sprinting toward early retirement or secretly wondering if you'd be bored out of your mind, this episode will make you rethink what freedom actually looks like.

Plus: Doug's T-shirt trivia takes a weird turn (as always), and the crew proves that the best financial conversations happen when nobody's trying to sell you a course.

What You'll Walk Away With:

• Why "enough money" doesn't equal "enough purpose"—and what to do about it

• How to think about work after financial independence (hint: it's not all or nothing)

• The identity crisis nobody warns you about when you stop working—and how to avoid it

• What financially independent people actually do with their time (spoiler: many keep earning)

• Permission to want both: financial security and meaningful work

Before You Hit Play, Think About This:

If money wasn't an issue tomorrow, would you keep doing what you're doing? If the answer is "no"—why are you still doing it? And if the answer is "yes"—what does that tell you about retirement?

Drop your take in the comments. The basement wants to know: Are you racing toward FIRE, or are you building something you never want to leave?

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.

Your Money Problems Aren't Math Problems (They're People Problems) SB1751 Oct 22, 2025

Show notes

Here's the secret nobody tells you: your money problems probably aren't math problems.

Joe Saul-Sehy and OG sit down with Carl Richards—financial planner, New York Times columnist, and the guy behind those brilliant "Sketch Guy" drawings that make money actually make sense. Carl's spent his career helping people untangle their relationship with money, and his big insight? Most of us are overthinking it.

Your financial plan shouldn't feel like a calculus final. It should feel like a map you can actually follow. Carl breaks down why emotions (not spreadsheets) drive most money mistakes, how to cut through the noise that keeps you paralyzed, and why the simplest plan is usually the one you'll actually stick to. If you've ever felt like you're "doing it wrong" because your strategy doesn't involve leveraged ETFs or cryptocurrency mining, this conversation will be a relief.

Then Joe and OG dive into the options trading debate. Is it a legitimate tool for managing concentrated stock risk, or just financial cosplay for people who watch too much CNBC? They break down when options might make sense, when they're just expensive complexity, and how everyday investors should think about them (if at all).

Plus: travel stories, Neighbor Doug's trivia (where he definitely brags about something), and proof that you can get smarter about money without wanting to take a nap.

What You'll Walk Away With:

Carl Richards' framework for simplifying your financial life—and why "The Behavior Gap" matters more than your rate of return
Why the emotions behind your money decisions matter more than the math (and how to work with them, not against them)
How to filter out financial noise and focus on the handful of things that actually move the needle
The truth about options trading: when it's a smart risk management tool and when it's just expensive gambling
Permission to keep your plan simple—even if it feels like everyone else is doing something fancier

This Episode Is For You If:

You feel like everyone else has figured out money except you
Financial jargon makes you want to hide under a blanket
You've got a solid income but still feel anxious about your money decisions
You'd rather learn through real stories than get lectured by a guy in a suit
You want to finally understand why you make the money choices you do (good and bad)

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-manage-your-money-goals-and-life-with-carl-richards-1751

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.