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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

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!
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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!
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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!

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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!
Learn more about your ad choices. Visit podcastchoices.com/adchoices

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!

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

Some people master reinvention. They move from one stage of life to the next with confidence, purpose, and an eye on long-term success. What if your financial plan could do the same?
In today’s roundtable, Joe is joined by Alyssa Maes, Roger Whitney (The Retirement Answer Man), and OG to talk about what it takes to build wealth that lasts—not just through one season of life, but through all of them.

🎯 Inside the episode:

What starting strong in your 20s and 30s really looks like

How to fight lifestyle creep and sharpen your personal brand mid-career

Why simplifying cash flow in retirement can be a game-changer

The power of habits, automation, and adaptability across all stages

And what consistent, thoughtful choices can do for your long-term success

The thread running through it all? Knowing who you are, where you're going—and letting your financial decisions reflect that.

We also sneak in a bit of trivia involving the most expensive comic book ever sold and a certain pop icon with a track record of breaking records (you can probably guess who).

This episode is about more than music or money—it’s about making every era of your life count.

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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Building Wealth Through Every "Era" of Your Life

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