The Stacking Benjamins Show

Latest Episodes:

Should You Drain Your Emergency Fund? (And 4 Other Money Questions Keeping You Up) SB1750 Oct 20, 2025

Show notes

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!

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.

What Lucky People Do Differently With Money (SB1749) Oct 17, 2025

Show notes

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!

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.

How to Deliver the “WOW” in Everyday Life (with longtime former Royal Caribbean Chairman and CEO Richard Fain) SB1748 Oct 15, 2025

Show notes

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!

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.

Gold Prices Hit All-Time Highs (What's That Mean To Us?) SB1747 Oct 13, 2025

Show notes

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!

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.

Build a Confident Early Retirement Plan (Without Overthinking It) SB1746 Oct 10, 2025

Show notes

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!

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.

Build Wealth AND Community Using This Strategy (with Mel Dorman) SB1745 Oct 08, 2025

Show notes

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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

5 Life-Changing Money Lessons from Jonathan Clements (SB1744) Oct 06, 2025

Show notes

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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The Missing Ingredients From Many Financial Plans (SB1743) Oct 03, 2025

Show notes

If your financial plan feels more like a vague wishlist than a real roadmap, this episode is about to change that. Live from the basement of YouTube HQ, Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long-Term Investors) roll up their sleeves and dig into the three most common — and costly — mistakes people make with their money plans. Whether you’re just starting out or you’ve been stacking for years, this conversation will help you turn “someday” into a solid plan you can actually follow.

The gang isn’t just talking theory — they’re breaking down the real reasons plans fail and how to fix them. From adding actionable next steps (instead of endless spreadsheets and good intentions) to weaving in crucial tax and estate planning moves, you’ll discover how to transform your financial plan into a tool that works for you. And because this is Stacking Benjamins, you can expect plenty of banter, relatable stories, and a trivia detour or two along the way.

By the time we wrap, you’ll know how to evaluate whether your plan is truly moving you toward your goals, how to communicate more effectively with your financial pros, and how to stop second-guessing every decision. It’s financial planning with fewer headaches, more confidence, and maybe even a little fun.

What You’ll Learn

Why most financial plans fail — and how to make yours bulletproof
The three crucial elements every solid plan needs (and most are missing)
How to incorporate tax strategies, estate planning, and real action steps

Smart ways to communicate with your advisor or team about what matters most

Questions to Consider

How to course-correct if your plan’s gone off the rails

Does your financial plan include clear, actionable steps — or just big goals?
Have you factored in tax and estate planning, or are you leaving those to chance?
Are you confident your plan will work in real life, not just on paper?

FULL SHOW NOTES: https://stackingbenjamins.com/three-things-missing-from-most-financial-plans-1743

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.

5 Steps to Your Best Retirement (with Jeremy Keil, CFP) SB1742 Oct 01, 2025

Show notes

Think your retirement plan is bulletproof? Think again. In this eye-opening episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by certified financial planner Jeremy Keil, CFP® to walk you through the steps to building a retirement plan that won’t crack under pressure. From mapping out your spending before you ever leave the workforce to crafting a tax strategy that keeps more money in your pocket, this conversation is your blueprint for making your golden years actually golden.

But just when you think you’ve got retirement handled, we throw a curveball: private equity. With giants like Goldman Sachs and T. Rowe Price trying to slip these complex investments into your 401(k), it’s time to ask whether “more opportunity” is really a good thing — or a trap for the unprepared. Joe and OG break down the risks, the realities, and what you need to know before you sign on the dotted line.

As always, we serve it all with a side of basement banter — from Doug’s trivia about the first issue of Playboy to a TikTok football moment you didn’t know you needed — plus real-life stories that prove retirement planning is as much about mindset as it is about math.

What You'll Learn In Today's Show:

The five key steps to building a retirement plan that works for you, not just a generic spreadsheet.
Why starting with your spending habits (not investments) can make or break your retirement success.
How to prepare for the emotional side of retirement — including those pesky “what now?” questions.
The surprising risks of private equity creeping into your 401(k) — and how to decide if it’s worth it.
Smart tax strategies to make your retirement money last longer.
How long-term care, market volatility, and unexpected expenses should factor into your plan.

Questions to Ponder During the Episode (and discuss with other Stackers!)

What’s one spending habit you need to understand now to avoid retirement surprises later?
How would you react if your employer added private equity options to your 401(k)?
Are you planning your retirement based on your lifestyle — or someone else’s idea of “enough”?

FULL SHOW NOTES: https://stackingbenjamins.com/five-steps-to-a-better-retirement-plan-with-jeremy-keil-1743

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.

Does The American Dream REALLY Costs $5 Million? (SB1741) Sep 29, 2025

Show notes

Think the American Dream is slipping out of reach? Think again. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug tackle one of the biggest financial questions of our time: how much does it really cost to live the life you want — and is it still possible? Spoiler alert: it is, but it takes more than a paycheck and a Pinterest board. We break down fresh research from Investopedia, the rising price tag of everything from healthcare to college, and how smart planning (and a little basement wisdom) can keep your dreams from turning into financial nightmares.

But this isn’t just another numbers game. Along the way, the gang shares stories from the road — including Joe’s brush with baseball’s most entertaining team — and digs into the strategies that can help you fight inflation, outsmart rising costs, and make compounding interest your best friend. Plus, we tackle big listener questions, from how to choose the right financial advisor to the best ways to set young adults up for success in a tougher economic landscape.

And because life isn’t all spreadsheets and savings goals, we round things out with some binge-worthy TV and movie picks for when you’re off the clock. It’s part money masterclass, part basement hangout — and all about helping you take real steps toward your version of the American Dream.

What You’ll Learn in This Episode

Why the “American Dream” isn’t dead — but why it may look different today.
The real costs behind homeownership, healthcare, education, and retirement (and how to plan for them).
Strategies for budgeting, saving early, and building systems that make your money work harder.
How to vet a financial advisor and what red flags to watch out for.
Smart ways to guide young adults toward financial independence.
The power of compounding interest and how to use it to your advantage.

Questions to Consider (and Discuss with Fellow Stackers)

What does the “American Dream” mean to you — and has that definition changed over time?
Which costs (housing, healthcare, college, etc.) feel most overwhelming right now, and how are you tackling them?
What’s one piece of financial advice you’d give to someone just starting their journey?

FULL SHOW NOTES: https://stackingbenjamins.com/the-rising-cost-of-the-american-dream-1741

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.

Our TOPPODCAST Picks

Follow Us

Stay Connected

The Stacking Benjamins Show

Related Podcasts

Links

Stay Connected