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

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!

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The Missing Ingredients From Many Financial Plans (SB1743)

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!

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

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!

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Does The American Dream REALLY Costs $5 Million? (SB1741)

What if tweaking just a few “knobs” in your 401(k) could mean the difference between retiring with confidence or wondering if you’ll ever stop working? In this spirited episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by three of our favorite money minds — Paula Pant from AffordAnything, Jesse Cramer from Personal Finance For Long Term Investors, and Lacey Langford from The MILMO Show — to break down everything you thought you knew (and a few things you probably didn’t) about retirement planning.

From the basics of employer matches and contribution strategies to the great Roth vs. Traditional debate, we’re exploring the smart moves that can supercharge your 401(k) — and the missteps that can quietly drain your future nest egg. Along the way, you’ll pick up clever tips, a few head-scratching stories, and some beer-fueled trivia that will leave you laughing harder than your HR rep when you ask if “401(k)” is the Wi-Fi password.

And because this is Stacking Benjamins, the conversation goes far beyond just investment allocations and tax advantages. We dig into why behavioral traps can derail your savings plan, how military families can maximize their benefits, and why understanding fees is one of the most underrated wealth-building moves you can make. So grab a pretzel, pull up a chair, and let’s talk about how to make your money work harder — so future you can kick back with a stein and say, “I nailed this retirement thing.”

 
How to “tune” your 401(k) like a pro — from employer matches to smart contribution strategies.

 
The real differences between Roth and Traditional accounts (and how to decide which is right for you).

 
Why understanding your 401(k) fees could add thousands to your future balance.

 
How military families can make the most of unique retirement benefits.

 
The biggest mistakes people make with their 401(k)s — and how to avoid them.

 
Plus: A special Oktoberfest-themed trivia showdown and plenty of basement banter.

FULL SHOW NOTES: https://stackingbenjamins.com/tweaking-your-retirement-account-1740

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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Strategies and Tactics to Maximize Your 401k (and common mistakes to avoid) SB1740

What if the secret to enjoying your job isn’t grinding harder but stepping back and rethinking how work fits into life? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome special guest Shemin Nurmohamed to unpack the Paris Paradox: balancing work and leisure without sacrificing ambition. From cultural perspectives on downtime to the productivity perks of unplugging, Shemin shows why working less might just help you accomplish more.

But that’s not all. What happens when your financial advisor suddenly jumps ship to another firm? The team digs into what it means for your money, your relationship with your advisor, and how to evaluate whether it’s time to follow—or finally shop around. Add in Doug’s trivia, a few stumbles down random rabbit holes, and our community’s contributions, and you’ve got a lively mix of practical advice and classic basement energy.

Whether you’re plotting your next vacation or just trying to figure out how to stop your inbox from running your life, this episode offers real-world strategies (and plenty of chuckles) to help you reset, recharge, and refocus.

 
Why time off is not laziness but fuel for better work and sharper decision-making.

 
How cultural differences around leisure can reshape your own approach.

 
What to do when your advisor changes firms (and how to spot a keeper).

 
Practical ways to build stronger connections and communities.

 
The “Two Beers and a Puppy” test: a surprisingly effective tool for evaluating relationships.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-work-less-live-more-and-love-your-job-1739

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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Work Less, Live More AND Perform Better at Your Job (SB1739)

Ever make a money move in the heat of the moment and wish you could take it back? That’s exactly why a rock-solid Investment Policy Statement (IPS) might be your most underrated financial tool. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug peel back the layers on IPSs—why they matter, how they save you from your own impulses, and the role they play in making sure your investment strategy actually sticks. Think of it as your financial GPS, keeping you on course when market turbulence makes you want to grab the wheel.

But it’s not just about avoiding panic-selling. The basement crew digs into the nuts and bolts of what a good IPS should include, from setting specific goals to handling liquidity needs and keeping your risk tolerance aligned with your lifestyle. You’ll also hear how rebalancing, governance, and regular reviews can transform your investments from “hope and pray” into a system you can rely on. Along the way, expect the usual SB tangents: a Joan Jett–themed trivia challenge, a TikTok tale about Apple Pay gone wrong, and more than a few moments where Doug forgets he’s not supposed to run the show.

By the end, you’ll not only understand how to create (or update) your IPS, but you’ll also see how it connects directly to building confidence in your financial plan. Whether you’re brand new to investing or a seasoned hand looking to sharpen your strategy, this episode delivers the blueprint.

 
Why an Investment Policy Statement is your best defense against emotional investing

 
How to set clear goals, liquidity rules, and risk guidelines for your portfolio

 
The pitfalls most people overlook when drafting an IPS (and how to avoid them)

 
Smart strategies for rebalancing and reviewing your plan without overcomplicating things

 
A cautionary tale from TikTok that reminds us all to keep our guard up with payment apps

 
Listener Q&A on stock sales and the quirks that come with them

Questions You'll Begin to Answer During the Episode:

 
Do you have a written IPS, and if so, does it reflect your actual goals—or just what you thought they were five years ago?

 
What emotional triggers most often tempt you to stray from your financial plan?

 
How often do you review your investments, and is it based on strategy—or headlines?

FULL SHOW NOTES: https://stackingbenjamins.com/simple-steps-for-better-money-management-1738

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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Stop Making Simple Investing Mistakes With an Investment Policy Statement (SB1738)

What happens when you throw a bunch of money nerds into one room, add microphones, and sprinkle in a little economic chaos? You get this live recording from FinCon in Portland, where Joe Saul-Sehy, Paula Pant, Jesse Cramer, and Matthew Tarr tackle today’s most pressing financial questions head-on—with plenty of laughs along the way. From housing headaches to healthcare hurdles, nothing is off the table as the crew breaks down the issues shaping your money right now.

Housing prices got you wondering if you should rent, buy, or just live in your car with an Amazon Prime subscription? We dig into the real trade-offs in today’s market. Worried about a looming recession or high-interest rates eating away at your financial confidence? You’ll walk away with strategies that keep you focused and resilient when headlines try to spook you. And for those plotting an early retirement, the group pulls apart the rising cost of healthcare and why conservative investment strategies may be your best friend.

At its core, this episode is about tuning out the noise and zeroing in on what matters: a solid plan, smart decisions, and a community of people who know that money is just the tool—not the destination. Whether you’re trying to hit FI, weather market storms, or simply avoid panic-selling your investments, this conversation from the heart of FinCon will leave you with perspective, strategy, and maybe even a grin.

 
Why renting vs. buying isn’t a one-size-fits-all answer (and what today’s market means for you)

 
How to prepare for recession chatter without losing sleep

 
The ripple effect of high-interest rates on your wallet and investments

 
Smart approaches to healthcare planning in early retirement

 
Practical strategies for building a strong investment plan that outlasts market swings

 
Reflections on community, optimism, and financial resilience from the FinCon floor

Points to Chew On:

 
Would you rather own a house in this market—or rent and keep flexibility?

 
How do you personally prepare for recession fears without derailing your long-term plan?

 
If healthcare costs keep climbing, how will that affect your retirement timing or strategy?

FULL SHOW NOTES: https://stackingbenjamins.com/live-from-fincon-2025-173

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 Are YOU Worried About Financially? (LIVE From FinCon 2025) SB1737

What happens when you stop playing it safe and start playing it smart? In this episode, Joe Saul-Sehy, OG, and Neighbor Doug sit down with David Gardner, co-founder of The Motley Fool, to explore how breaking traditional investing “rules” can sometimes lead to the biggest wins. From his early career to building a community of investors who think differently, David shares the lessons that shaped his approach and why focusing on long-term investing (with a dash of joy) is the key to building wealth.

This isn’t just theory—David opens up about the real-world evolution of financial advice, the importance of conscious capitalism, and why advisors need to shift from just picking stocks to becoming true guides in an era where investment products are commodities. Along the way, the basement crew mixes in a few unexpected detours (yes, including some movie talk), reminding us that money doesn’t have to be boring to be meaningful.

If you’ve ever felt like the “safe” path with your money was leading you in circles, this episode offers a fresh perspective from one of the most influential voices in modern investing. Get ready to rethink the rules, laugh along the way, and come away with strategies to make your portfolio—and your life—more rewarding.

 
Why breaking conventional investing “rules” can sometimes be your best move

 
The evolution of The Motley Fool and its impact on everyday investors

 
How long-term thinking beats short-term noise in building wealth

 
The role of conscious capitalism and why businesses matter beyond profits

 
Why financial advisors need to pivot their focus to guidance, not just products

 
How criticism shaped David Gardner’s career and what he learned from it

Points to Ponder During the Episode

 
When’s the last time you broke a “money rule,” and did it pay off—or backfire?

 
Do you believe financial advisors should focus more on guidance than investment selection?

 
What’s one company or stock you’ve stuck with long-term—and why?

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David Gardner on Breaking the Rules of Investing (SB1736)

What really derails retirement dreams? Spoiler alert: it’s not always the stock market or your 401(k). Sometimes it’s sneaky habits—like leaning too hard on your house as a retirement plan or ignoring how long you might actually live—that quietly gnaw away at your financial future. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug dig into the most common middle-class retirement killers and how you can sidestep them.

But this isn’t your average checklist of “don’t do that.” The team dissects questionable advice floating around internet forums, debates stock splits and diversification, and even finds time to unravel why owning a cat might make you a magnet for gangster-level problems. Add in Doug’s trivia about a famous singer’s real name, and you’ve got an episode that’s equal parts practical and delightfully unpredictable.

Whether you’re worried about stretching your retirement savings or just looking for sharper ways to think about financial advice, this episode offers both reassurance and reality checks. So grab your favorite mug (or maybe your cat), settle into your seat, and get ready to learn how to protect your retirement from the biggest threats—while laughing at the absurdity along the way.

What You’ll Learn in This Episode:

 
The habits that quietly sabotage retirement plans (and what to do instead)

 
Why your house may not be the slam-dunk retirement strategy you think it is

 
The risks of living longer than you expect—and how to plan for it

 
How to sniff out sketchy financial “tips” before they lead you astray

 
The surprising traps behind stock splits, diversification myths, and overconfidence

 
Why even well-meaning advice can backfire if you don’t look at the big picture

Questions to Ponder (or Debate in the Basement Facebook Group):

 
Which retirement habit do you think trips people up the most—and why?

 
If you had to choose, would you rather rely on your house equity or a diversified portfolio to fund retirement?

 
What’s the worst financial “tip” you’ve ever heard online (or maybe even followed)?

FULL SHOW NOTES: https://stackingbenjamins.com/habits-that-destroy-middle-class-retirement-dreams-1736

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 Sidestep the 4 Culprits Wrecking Middle Class Retirement (SB1735)

How do you put the brakes on spending so much money? ....... Our special guest today is Ashley Feinstein Gerstley, author of The Thirty Day Money Cleanse, and she's an expert in cleaning up your budget. We'll talk with her and our team about a recent Budgets Are Sexy blog post in which blogger J. Money lays out how he avoids spending money. What games do you play with yourself to distract yourself from spending money. Plus, two contributors you know and love, Len Penzo from the LenPenzo.com blog, and from Afford Anything, Paula Pant.
Halfway through the roundtable we'll take a break for our Friday Fintech segment and talk to DeAnn O'Donovan from AHP Servicing. AHP Servicing is a company that's setting out to help people who are struggling with their mortgages find ways to stay in their homes.
We'll also answer a MagnifyMoney.com question from Paul, who has the opportunity to buy shares of a new company. He's sure the price is going to jump up. Should he use he cash he has on hand to buy shares, or take out a loan to get even more shares?
And of course, we'll still have time for Doug's trivia.
Thanks to Masterworks for supporting Stacking Benjamins. Visit Masterworks.io and reserve your shares now. See disclaimer at Masterworks.io/disclaimer.
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Our Favorite Ways To Distract Ourselves From Spending (plus an intro to AHP Financing)

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