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StackingBenjamins.com | Cumulus Podcast Network

Named the Best Personal Finance Podcast by Bankrate.com and Kiplinger, The Stacking Benjamins Show features a light and friendly tone. Hosts Joe Saul-Sehy and OG aim to make financial literacy fun for all as they sit around the card table in Joe's Mom's half-finished basement and talk with experts about personal finance, saving, investing, and important money trends. As Fast Company once wrote, the Stacking Benjamins podcast "strikes a great balance of fun and functional." So join Joe and OG every Monday, Wednesday and Friday as they read your letters, discuss major headlines, and throw in some trivia and laughs for free.

The Stacking Benjamins Show

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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Real Money Horror Stories (And How Not to Star in Your Own) SB1753

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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You've Got Enough Money to Quit. Should You? SB1752

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!
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Your Money Problems Aren't Math Problems (They're People Problems) SB1751

You've got questions. We've got two CFPs and a former planner ready to hash it out.

Joe Saul-Sehy, OG, Doug, and CFP Anna Allem tackle the money decisions you're actually losing sleep over—and here's the thing: they don't always agree on the answer. That's the point.

Should you drain your emergency fund to pay off debt? Is whole life insurance for your kids a smart move or an expensive mistake? How much life insurance do you actually need (not what some calculator tells you)? And when life throws you a curveball—layoff, surprise expense, major purchase—what's the move?

With Joe Saul-Sehy's 16 years in financial planning, OG's CFP perspective, and Anna's insights, you'll hear how experienced voices think through these decisions differently—and why your answer might be different than all of theirs. Because the real skill isn't finding THE right answer; it's learning how to make YOUR right call.

This episode is for anyone who's ever stared at their bank account thinking, "I know I should do something... but what?"

Plus: Doug delivers trivia about the first auto insurance policy (because of course), the gang weighs in on athlete endorsements and reverse mortgages, and there's a TikTok money tip that sparks some debate.

What You'll Walk Away With:

• How experienced financial minds approach the emergency fund dilemma differently—and what that means for your situation

• The whole life insurance debate: when it makes sense for kids and when you're better off elsewhere

• A framework for figuring out how much life insurance you actually need—and why the "rules of thumb" don't always work

• What to do when your financial plan meets real life (layoffs, surprise bills, major purchases)

• The confidence to make a decision even when experts would handle it differently

Before You Hit Play, Ask Yourself:

What's the one money question you keep Googling but still don't feel confident about? If you're second-guessing your emergency fund, your insurance, or a big financial move, this episode is your permission to stop spinning and start deciding.

Got a question we didn't cover? Call in to the show! StackingBenjamins.com/Voicemail

FULL SHOW NOTES: https://stackingbenjamins.com/answering-your-burning-financial-questions-1750

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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Should You Drain Your Emergency Fund? (And 4 Other Money Questions Keeping You Up) SB1750

Think some people just have all the luck? Think again.

Joe, OG, Paula Pant (Afford Anything), and Chris Luger (Heavy Metal Money) break down what separates people who catch breaks from those who don't...and spoiler alert: it's not about being in the right place at the right time.

It's about what you DO when opportunity shows up. And before that: how you create the conditions for opportunity to find you in the first place.

This episode digs into three moves that make luck happen: staying curious (even when you think you know the answer), being generous (yes, it pays off financially), and staying flexible when life throws you a curveball. Whether you're stuck on a money decision, feel like you're missing opportunities, or just want to stop watching other people win, this conversation will shift how you see "luck."

Plus: Doug's trivia gets weird (what even IS a buttload?), the gang debates pumpkin spice season, and you'll hear stories that prove the best financial wins rarely go according to plan.

What You'll Walk Away With:

 The one thing "lucky" people do that creates more opportunities—and how to start doing it today

 Why helping others might be your best financial strategy (and the science behind it)

 How to spot opportunities you're currently walking past

 What to do when your financial plan falls apart (hint: the flexible win)

 Permission to try something new, even if you're not sure it'll work

Before You Hit Play, Think About This:

What's one time something good happened to you? ...not because of random chance, but because you were curious, helped someone, or said yes to something outside your comfort zone? That's the kind of "luck" we're talking about.

Got a story? We want to hear it. Drop it in the comments or share it in your podcast app.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-find-more-luck-with-your-money-1749

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 Lucky People Do Differently With Money (SB1749)

You don’t have to command a cruise ship (or a boardroom) to lead with purpose. On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome Richard Fain, longtime chairman and former CEO of Royal Caribbean Group, for a conversation that’s not about corporate leadership… but about life leadership.

Richard shares timeless lessons he learned from decades steering one of the world’s most innovative companies—lessons that apply just as powerfully to parenting, coaching your kid’s soccer team, running a PTA fundraiser, or simply trying to create more joy at home. You’ll hear how to dream bigger about your own life, build a culture of kindness and excellence in small groups, and turn the ordinary moments around you into opportunities to “deliver the WOW.”

Of course, this wouldn’t be the basement without a few money detours. The crew also breaks down new 401(k) rules and annuity updates, debates whether tax flexibility beats fancy planning, and celebrates Doug’s birthday with trivia, laughter, and a few movie reviews along the way.

By the end, you’ll walk away inspired to bring a little more vision, creativity, and generosity into every corner of your world. No cruise ship required.

What You’ll Learn

 
How to lead from wherever you are: Richard’s lessons on building strong teams, communities, and families. No corner office needed.

 
Turning the ordinary into extraordinary: Simple ways to “deliver the WOW” at home, work, or anywhere people count on you.

 
Dreaming bigger about your life: Why bold vision isn’t just for CEOs; it’s for anyone looking to create meaning and momentum.

 
Financial updates you can use: New 401(k) rules, annuity insights, and practical tips to strengthen your plan.

 
The lighter side of leadership: Trivia, birthday celebrations, and a few fun detours (because we can’t resist).

Questions for the Basement

 
What’s one way you could “deliver the WOW” in your own life this week?

 
Who’s a leader in your everyday world (at home, work, or your community) who’s made an impact on you?

 
How can dreaming a little bigger change the way you approach your next financial or personal goal?

FULL SHOW NOTES: https://stackingbenjamins.com/better-money-habits-with-richard-fain-1748

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 Deliver the “WOW” in Everyday Life (with longtime former Royal Caribbean Chairman and CEO Richard Fain) SB1748

When gold shines, so do the hot takes, and today, the Stacking Benjamins crew dives into what this record-breaking surge really means for your money. Joe Saul-Sehy, OG, and Neighbor Doug kick off the week with their signature Monday salute to our troops before digging into the glittering headlines: gold prices are hitting new highs… but does that make it a smart investment or just financial fool’s gold?

From breaking down why gold spikes when markets wobble to questioning whether it’s truly the “safe haven” it’s cracked up to be, the guys unpack the myths, mindset, and math behind precious metals. You’ll also hear fresh strategies for weathering volatile markets, balancing your asset allocation, and staying cool when everyone else is panicking. And of course, Doug drops in with a TikTok Minute, a trivia challenge, and one listener’s wild math-powered success story that somehow involves an Olive Garden. (Breadsticks optional.)

So grab your coffee, your calculator, and maybe your lucky coin—because this episode proves that in the unpredictable world of investing, sometimes the smartest move is knowing why you’re holding what you’re holding.

What You'll Learn

 
Why gold prices are climbing and what that might signal about the global economy.

 
The myth of “safe haven” assets: When gold works, when it doesn’t, and why diversification still wins.

 
Smart portfolio moves for volatile times—without letting emotions tank your returns.

Real-life stories and lessons from Stackers proving that good math (and a little luck) can go a long way.

The lighter side of finance: Breadsticks, TikTok, and trivia—because learning about money doesn’t have to feel like homework.

Questions You'll Want to Answer:

 
Do you view gold as an investment, insurance policy, or just a shiny distraction?

 
What’s your go-to strategy when markets start getting rocky?

 
Have you ever made a “safe” financial move that didn’t turn out as safe as you thought?

FULL SHOW NOTES: https://stackingbenjamins.com/gold-and-other-investments-for-bear-markets-1747

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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Gold Prices Hit All-Time Highs (What's That Mean To Us?) SB1747

Who says you have to wait until 65 to clock out and start living your best life? On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, Paula Pant (Afford Anything), OG, and special guest Sean Mullaney—author, CPA, and early retirement strategist—explore how to design a life that lets you walk away from the office sooner and happier.

From tax-smart withdrawal strategies to dialing in your lifestyle design, this conversation pulls back the curtain on what it really takes to achieve early financial independence. You’ll hear practical steps for aligning your money with your values, structuring your investments for flexibility, and ensuring your plan can survive market dips and surprise expenses. Along the way, the team debates Roth vs. Traditional retirement accounts, shares personal insights from FinCon, and delivers a few laughs (and groans) in Doug’s trivia corner.

Whether you’re in your 30s planning a slow exit or in your 50s wondering if it’s too late to pivot, this episode is your guide to crafting a retirement plan that works as hard as you do—without losing sight of the joy along the way.

What You'll Learn

 
How to design your early retirement plan: The building blocks of lifestyle design and financial freedom.

 
Tax-efficient investing: When to prioritize Roth vs. Traditional accounts—and why both can play a role.

 
Withdrawal strategies that work: How to avoid tax traps and keep your plan sustainable.

 
The mindset shift: Why retiring early isn’t about leaving work—it’s about moving toward purpose.

 
How to “future-proof” your finances: Guarding against inflation, longevity risk, and unexpected curveballs.

Questions to Ponder During Today's Show:

 
What would your perfect day look like if you didn’t have to work tomorrow?

 
Would you be willing to earn less now if it meant retiring five years earlier?

 
What does “enough” look like for you—and how do you know when you’ve reached it?

FULL SHOW NOTES: https://stackingbenjamins.com/building-your-early-retirement-plan-1746

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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Build a Confident Early Retirement Plan (Without Overthinking It) SB1746

What if building wealth wasn’t just about stacking dollars — but also stacking good deeds? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG sit down with Mel Dorman, a powerhouse real estate investor who turned humble beginnings (yes, dumpster diving beginnings) into a thriving portfolio of 34 rental units in just five years. And she didn’t just build wealth — she built community along the way.

From negotiating creative seller-financed deals to forging partnerships that benefit both investors and neighborhoods, Mel shares how real estate can be a tool for connection as much as for cash flow. You’ll learn how she leverages relationships, uses alternative financing to scale quickly, and even flips properties without traditional bank loans — all while staying grounded in her mission to help others.

But that’s not all: Joe and OG also break down the latest Federal Reserve moves and what they mean for your wallet. And of course, Neighbor Doug drops by with his signature trivia to remind us that building wealth is serious business… but it’s okay to have some fun while you’re at it.

What You'll Learn

 
Creative ways to build wealth: How seller financing can unlock deals you never thought possible.

 
The power of purpose: Why combining community impact with real estate investing is a winning formula.

 
Real-world strategies: Mel’s journey from zero to 34 units — and the lessons she learned along the way.

 
How Fed rate changes affect you: What rising (or falling) rates mean for investors and homeowners.

 
Financing myths busted: Why traditional bank loans aren’t the only way to grow a portfolio.

Points to Ponder:

 
Could creative financing open doors for your investing goals?

 
How might building stronger community ties improve your financial outcomes?

 
Are you prepared for how interest rate changes could impact your next big money move?

This episode isn’t just a guide to real estate success — it’s a reminder that money works best when it works for everyone. Grab a notebook, pour yourself something caffeinated, and join us for a conversation that just might change how you think about wealth building.

FULL SHOW NOTES: https://stackingbenjamins.com/real-estate-investing-in-your-community-1745

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

Build Wealth AND Community Using This Strategy (with Mel Dorman) SB1745

What if the key to a richer life isn’t about chasing the next hot stock or grinding harder — but learning to master the timeless truths of money? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug pay tribute to legendary financial writer Jonathan Clements by revisiting five of his most impactful lessons. These aren’t complicated formulas or secret hacks — they’re the kind of deceptively simple ideas that change the way you think about money, work, and what truly matters.

We’ll explore why prioritizing financial stability before passion can actually lead you to a more fulfilling career, how “winning by not losing” may be the most underrated investing strategy of all time, and why patience isn’t just a virtue — it’s a tax strategy. Along the way, we’ll talk about how to strike the right balance between frugality and joy and why living your life may be the best investment you ever make. Plus, we help Stacker Kat tackle a tricky severance situation and share tips on how to put that cash to work without capsizing your financial plan.

If you’ve ever wondered how to align your money with a life you actually love, this conversation is the perfect mix of inspiration and actionable wisdom. Grab your coffee mug and settle into Mom’s basement — this is an episode you’ll come back to whenever you need a financial reset.

What You'll Learn

 
The real reason you shouldn’t chase passion too soon — and what to do instead

 
How to avoid the most common (and costly) financial mistakes

 
Why patience pays: how time turns taxes into opportunity

 
How to balance frugality with actually living a fulfilling life

 
Smart ways to use severance, high-yield savings, and investing strategies together

Points To Ponder:

 
Which of Jonathan Clements’ five money lessons hits closest to home for you?

 
Have you ever faced a tough severance decision like Stacker Kat’s? What did you do?

 
Do you believe financial stability should always come before passion — or is there a time to flip that script?

FULL SHOW NOTES: https://stackingbenjamins.com/five-pearls-of-wisdom-from-jonathan-clements-1744

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

5 Life-Changing Money Lessons from Jonathan Clements (SB1744)

Is your 401(k) quietly working for you… or quietly working against you? In the first half of this episode, Joe Saul-Sehy, OG, and Neighbor Doug tackle the most common 401(k) slip-ups that even seasoned savers make—and how to turn yours into a retirement-building machine.

Then, in the second half, we turn to a problem many Stackers don’t see coming: going from saving to spending in retirement. Stacker Joel in Cleveland asks how to make the leap without feeling like you’re sabotaging your future. Drawing on OG’s real-world experience guiding clients through this tricky transition and Joe’s research into the psychology of money, we share practical steps to help you spend without guilt, align your withdrawals with your values, and actually enjoy the freedom you’ve worked so hard for.

Here’s what you’ll learn in this episode:

 
The most expensive 401(k) mistakes—and how to fix them today

 
Why employer matches are truly “free money” (and how to grab them)

 
Smart moves for rolling over old 401(k)s and navigating vesting schedules

 
The pros and cons of holding company stock in your retirement account

 
Why the saving-to-spending switch can feel so uncomfortable—and how to get past it

 
A simple mindset shift that helps retirees live more fully without blowing their plan

 
How to turn your nest egg into a joy-producing income stream

Whether you’re in the middle of your career or staring down your first year of retirement, this episode will help you protect what you’ve built, optimize your plan, and make the most of your money—without second-guessing yourself.

FULL SHOW NOTES: https://stackingbenjamins.com/common-401-k-mistakes-1720

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

How To Fix 8 of the Most Common 401k Mistakes (SB1720)

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