The Stacking Benjamins Show

By Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFPBusiness Education Investing

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The Stacking Benjamins Show episodes

August 13, 2025How One Entrepreneur Constructed a Better Tomorrow (with Cheryl McKissick Daniel) SB1721
Ever wonder how to build a career, business, or financial plan that actually lasts — no matter what life throws at you? This week, we’re bringing you lessons from someone who’s done it for more than five generations. Cheryl McKissick Daniel, president and CEO of McKissick & McKissick, joins Joe and OG to share the strategies her family has used to overcome obstacles, land major deals (like the arena in Brooklyn and countless buildings on the historic register of places), and turn connections into opportunities. Whether you’re growing a business, climbing the career ladder, or managing your money, you’ll walk away with practical ideas to strengthen your network, protect your reputation, and keep moving forward.
From the art of negotiation to turning big challenges into bigger wins, Cheryl offers insights you can use right now to build momentum. We’ll explore how revisiting your financial plan regularly can help you avoid surprises, why reputation is an asset you can’t afford to neglect, and how a strong team can take you further, faster.
Plus, we’ll take a break for our TikTok Minute to look at what happens when your vacation budget disappears in the name of “fun” spending. And in our headline segment, we’ll cover important Medicare and insurance updates that could save you money and headaches later.
Here’s what you’ll learn in this episode:
How to use your reputation as a currency that opens doors and attracts opportunities

Strategies for building a network that works for you (even when you’re not in the room)

Lessons from landing multi-million-dollar deals — and how to apply them to your own negotiations

Why regularly reviewing your financial plan can save you from costly surprises

Smart adjustments to Medicare and insurance that protect your money and peace of mind

How to turn adversity into momentum, whether in your career or personal finances

A lighthearted look at how “just a little fun” can destroy your budget faster than you think
FULL SHOW NOTES: https://stackingbenjamins.com/story-about-building-america-1721
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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1 hr 3 min
August 11, 2025How To Fix 8 of the Most Common 401k Mistakes (SB1720)
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!

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1 hr
August 08, 2025Hot Financial Takes: Are You In or Out? SB1719
Get ready for a rapid-fire roundtable packed with personal finance opinions that might challenge your own money playbook. In this episode, Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and Don McDonald (Talking Real Money) join Joe and OG to declare whether they're in or out on some of the most polarizing financial strategies.
Whether you're just getting started or leveling up your financial life, this episode is full of practical wisdom, contrarian views, and a few laughs along the way. Oh—and somewhere in there, we may or may not sneak in a birthday surprise for one of our favorite Stackers. 🎂😉
Why some pros still say "cash only" is best for beginners—and why others strongly disagree

The real trade-offs of delaying homeownership in today’s market

What types of insurance you actually need (and which may just be money drains)

When hiring a CPA is a gamechanger vs. when it's overkill

How to evaluate target date funds: genius or lazy?

Whether it’s finally time to drop collision insurance on that 15-year-old car

How to choose between Roth and Traditional 401(k) strategies

The one estate planning move nearly everyone overlooks
FULL SHOW NOTES: https://stackingbenjamins.com/jeff-lund-birthday-special-1719
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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53 min
August 06, 2025Master the Art of Negotiation with Paula Pant (SB1718)
Think negotiation is just for boardrooms and car dealerships? Think again. In this episode, we bring in Paula Pant from Afford Anything to show how negotiating—done well—can level up your finances, your relationships, and yes, even who does the dishes.
Paula breaks down why many of us fear negotiation, how to overcome those internal roadblocks, and how setting clear “aspiration” and “reservation” points can lead to more confident conversations (and better outcomes). Whether you’re asking for a raise or trying to avoid unloading the dishwasher for the fifth night in a row, her tactics are practical and empowering.
Also in this episode:
What most people miss about their workplace retirement plans, and whether adding a managed account is the edge you’ve been missing

A viral TikTok proposal on setting your kids up for millions—can it really work, or is it just social media smoke?

Doug delivers trivia and 1970s television references like only he can

And we remember a cherished interview, David Gergen
This episode is packed with useful strategies, real talk, and a few basement detours—including mafia negotiations, Lucille Ball’s business savvy, and a heated debate over nostalgic TV shows.
Whether you’re trying to grow your wealth, negotiate more confidently, or just dodge financial TikTok traps, we’ve got something in here for you.
FULL SHOW NOTES: https://stackingbenjamins.com/how-to-improve-your-negotiating-skills-with-paula-pant-1718
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
1 hr 14 min
August 04, 2025A Sandwich Guide to Navigating Inflation (plus how to plug 401k "leakage") SB1717
Is your grocery bill beefier than your sandwich? This week, Joe Saul-Sehy, OG, and Neighbor Doug unpack inflation in a way that only we can—by biting into Len Penzo’s Annual Sandwich Survey. Yes, prices are up, and yes, you can still eat well without triggering a credit card crisis.
But it’s not just meat and mustard on today’s menu.
We’re also serving a fresh look at 401(k) “leakage”—that drip-drip-drip of hardship withdrawals that's turning your retirement plan into a leaky faucet. You’ll get pro-level insight on how to patch those holes before your future income soaks the floor.
And if you’re paying for (or dreading paying for) college, Christine from the Stacker community, who works in higher ed, joins to offer sharp and timely advice on keeping costs in check—from completing the FAFSA to finding overlooked aid.
Len Penzo’s Sandwich Index
Which sandwiches give you the most delicious bang for your inflation-adjusted buck? (Spoiler: bologna stages a quiet comeback.)

401(k) Trouble Brewing
Hardship withdrawals are on the rise. Why it matters, how to avoid them, and what better options exist when life throws you a cash crisis.

Tracking Expenses Like a Pro
Joe, OG, and Doug explore the subtle ways inflation seeps into your budget—and how paying attention to where your money leaks gives you power back.

Higher Ed, Lower Bills
Stacker Christine breaks down must-know tips on navigating skyrocketing tuition, including a FAFSA pep talk that could save you thousands.

Tuna vs. Roast Beef: The Sandwich Showdown
Plus: Is the BLT still king? Can the humble tuna salad hold its ground against the mighty Big Mac? And where does salami fit into the sandwich power rankings?

Trivia, Movie Talk, and Park City Tales
No Stacking Benjamins episode is complete without a detour or three—from Doug’s trivia trap to stories from the road and screen.
Takeaway for Stackers:
In high-cost times, it’s the small wins—like swapping in store brands, packing a lunch, or tracking that budget leak—that give you the edge. And while it’s tempting to ignore those tiny cracks in your retirement plan or daily spending, you’re much better off fixing them before the flood.
Want to brag about your favorite money-saving sandwich? Drop into the Basement Facebook group and share it—bonus points if it doesn’t involve bologna.
FULL SHOW NOTES: https://stackingbenjamins.com/len-penzo-2025-annual-sandwich-survey-1717
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
1 hr 19 min
August 01, 2025What Would YOU Do With $50,000? (SB1716)
You just came into $50,000—no strings attached. Do you crush your debt? Supercharge your retirement? Blow it all on a podcasting-themed backyard grotto?
In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Jesse Cramer (The Best Interest) gather around the card table in Mom’s basement to tackle one of the most common “someday” questions in personal finance: What do you do when a windfall lands in your lap?
Whether it's an inheritance, work bonus, or prize money (maybe you finally won that game show you keep applying to), the panel explores what smart, emotionally grounded, and goal-aligned decisions look like in the face of sudden cash.
Start With the Why
Before you touch a dime, the crew walks through the importance of mindset, goals, and not falling into the “I deserve it” trap that has sunk many a lucky winner.

Debt vs. Invest vs. Enjoy
High-interest debt? Retirement accounts? Travel dreams? The panel weighs each strategy—and surprises us with their personal priorities.

Behavioral Finance & Windfall Psychology
Why do people tend to mismanage unexpected money? From mental accounting to lifestyle creep, learn the hidden traps and how to sidestep them.

The 401(k) Match Dilemma
Is it better to max out tax-advantaged accounts or build an emergency fund? The team hashes out smart order-of-operations for stacking your windfall right.

Trivia Break: St. Paddy’s Parade Edition
Neighbor Doug makes sure you don’t learn too much without a little distraction. Can you guess when the first St. Patrick’s Day parade was held?

How They’d Spend It
Ever wonder what Joe, OG, Paula, or Jesse would do with an extra 50 grand? From practical moves to guilty pleasures, we get a peek into each of their financial brains.
Don’t let windfalls drift into “found money” syndrome—align with your long-term goals first.

Paying off high-interest debt = guaranteed return. But balance it with your future-focused investments.

Emotional awareness is just as crucial as spreadsheets when a windfall hits. Take a beat before making decisions.

Give yourself permission to enjoy some of the money—just make sure it’s intentional, not impulsive.
Got a windfall story or dream scenario? Tell us how you’d handle an extra $50K in our Basement Facebook group. Let’s see who would invest it, who would renovate the kitchen, and who would finally launch that mobile alpaca petting zoo.

FULL SHOW NOTES: https://stackikngbenjamins.com/how-to-treat-a-financial-inheritance-1716
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.
1 hr 4 min
July 30, 2025How to Make Better Decisions Using Math (with Ted Dintersmith) SB1715
High school math left most of us staring blankly at the board, convinced compound interest was just a fancy way to say "confusing." But what if math could be fun, relevant, and—dare we say—life-changing?
In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome economist, education reformer, and documentary filmmaker Ted Dintersmith to the basement for a conversation that makes math feel less like a chore and more like a cheat code for life.
Dintersmith, best known for his education advocacy and the acclaimed documentary Most Likely to Succeed, joins us fresh off the release of his latest book, Aftermath—a compelling look at how we rethink learning in a world that’s evolving faster than ever. With over a decade visiting 500+ schools and a deep passion for practical math, Ted shares how skills like estimation, probability, and prediction can help you make smarter decisions—especially when it comes to your money.
Why Prediction Beats Perfection
Ted explains why being roughly right about your spending, investing, and life planning is more powerful than being precisely wrong.

Consumer Math is the Real MVP
From family budgets to grocery store run-throughs, Dintersmith makes a case for math that actually applies to your everyday decisions—and shows how parents and educators can teach it at home.

A Fourth-Grade Science Test Gone Wrong
An unforgettable story about how one exam nearly crushed a curious kid’s confidence… and what it says about how we measure learning.

The Financial Advisor Dilemma Solved
Joe Saul-Sehy and OG unpack the key differences between bank advisors and independents, including fee structures, fiduciary responsibilities, and what really matters when choosing your financial guide.

Lights, Camera, Reform
Dintersmith shares the powerful stories behind his documentaries—including Most Likely to Succeed and the upcoming Multiple Choice—and why his new book Aftermath is a must-read for anyone who believes education should prepare us for real life.

The Psychology of Math Anxiety and Money Mistakes
We explore how bad math experiences lead to financial decision paralysis, and how to rebuild confidence one calculation at a time.

Neighbor Doug’s Trivia Takes the Stage
Whether it connects to math or not, Neighbor Doug delivers his signature trivia moment with flair—and possibly a tangent or two.
Math shouldn’t be a barrier to better money decisions. This episode arms you with a fresh mindset for yourself, your kids, and maybe even your school board. If you’re a math teacher, financial coach, or just someone who once cried over fractions, we want to hear from you.
Join the conversation in our Facebook group, The Basement, and tell us: How are you making math practical—or how do you wish you’d learned it?
FULL SHOW NOTES: https://stackingbenjamins.com/math-that-you-need-in-your-life-1715
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
1 hr 21 min
July 28, 2025How to Turn 2025's New Tax Rules Into Big Savings (SB1714)
Big changes are coming to the tax code—and that could mean big savings if you know where to look. On today’s episode, Joe, OG, and Doug break down the most important updates in the 2025 tax laws and share smart, simple ways to keep more of your hard-earned cash.
Whether you're a spreadsheet-loving tax nerd or someone who still asks, “Wait, do I have to file?”—this episode will help you navigate the new rules like a pro.
Here’s what we unpack:
The 2025 Tax Overhaul: What changed, what stayed the same, and how it affects your bottom line

Credits vs. Deductions: Why that $1 credit might be worth more than a $5 deduction (math, but fun)

Above-the-Line Moves: Claim valuable deductions without itemizing

New Wins for Givers and Drivers: Above-the-line charitable contributions AND (drumroll…) personal auto loan interest is back!

Family Tax Breaks: Expanded dependent care accounts and beefed-up child credits

50 and Thriving: New 401(k) catch-up rules that can help you max out your retirement

Listener Mailbag: JJ asks how to contribute more to his 401(k) after age 50—and we bring the strategies

The TikTok Minute: Because money wisdom can live on the internet too

Doug’s Trivia & Financial Shenanigans™: Of course
You’ll walk away with clear, practical takeaways that could add thousands to your bottom line—without needing to read the tax code (you're welcome).

FULL SHOW NOTES: https://stackingbenjamins.com/upcoming-tax-changes-1714
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.
48 min
July 25, 2025Climbing the Wealth Ladder: Conquering Retirement Fears (with Mark Trautman) SB1713
What if the scariest part of retirement isn’t running out of money—but losing your sense of identity? This week on The Stacking Benjamins Show, we tackle the fears that hold so many people back from financial independence and a joyful, purpose-filled retirement.
Joe Saul-Sehy and Doug are joined by an all-star panel of financial thinkers:
Mark Trautman (Mark’s Money Mind)

Paula Pant (Afford Anything)

Jesse Cramer (Personal Finance for Long-Term Investors)
Together, they unpack the emotional, practical, and strategic side of planning your next chapter—whether you're closing in on retirement or still working toward it.
The biggest fears about retirement: from running out of money to running out of meaning.

The “one more year” syndrome: why it's so tempting to delay and how to break through.

Time freedom vs. financial freedom: how to align your life goals with your money strategy.

Tactics to conquer fear: income layering, diversified portfolios, annuities, and rental properties.

Psychology matters: why no spreadsheet ever solved a midlife identity crisis.

Real stories from the panel: wins, struggles, and lessons from guiding others through retirement transitions.

Planning for healthcare and long-term care: because your body didn’t get the early retirement memo.

Plus, the usual basement mayhem: trivia, playful host banter, and a few unexpected laughs (we won’t call them “funny”—you know the rule).
Mark’s Money Mind podcast

Afford Anything podcast

Personal Finance for Long-Term Investors

AARP: Retirement Readiness & Addressing Fear

Blog post: “Fear Will Hold You Prisoner. A Diversified Portfolio Will Set You Free.”
Retire to something, not just from something. Purpose beats spreadsheets.

Understand your income plan. Know where the money will come from, rain or shine.

Plan for healthcare now, not later. Medicare, long-term care, and medical surprises deserve your attention.

Don’t go it alone. The best plans are ones you understand, but it helps to get advice from trusted sources.
Whether you’re on the cusp of calling it quits or still deep in the grind, this episode will help you prepare—not just financially, but mentally and emotionally—for a retirement you’ll love.
FULL SHOW NOTES: https://stackingbenjamins.com/what-is-holding-you-back-from-reaching-your-goals-1713
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
🎧 Dive deeper, grab resources, and check out past episodes at StackingBenjamins.com

Enjoy!

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58 min
July 23, 2025Understanding Your Financial Roadmap (with Nick Maggiulli) SB1712
What do your financial priorities look like when you're just getting started... or when you're sitting on $100 million? If you’re still stuck trying to figure out how to max out your Roth IRA and also afford dinner, this episode’s going to walk you through what might be coming next—without promising you a yacht by Tuesday.
This week on The Stacking Benjamins Show, Joe Saul-Sehy, O.G., and Doc G (Jordan Grumet) are joined by Nick Maggiulli, Chief Operating Officer at Ritholtz Wealth Management and author of Of Dollars and Data, to talk about lessons from his new book: The Wealth Ladder. Nick breaks down the six wealth levels, from scraping together your first emergency fund to navigating the complexities of generational wealth.
They explore:
Why increasing your income early on trumps frugality (sorry, coupon clippers).

What “wealth plateaus” really look like, and how to recognize when your strategy needs to evolve.

The hidden trap of goal obsession, featuring a cameo from world #1 golfer Scottie Scheffler.

The true cost of career choices, and why opportunity cost might be the silent killer of long-term growth.

Why content and code are two of the most powerful wealth-building levers available (especially when they scale without needing a lunch break).
Whether you're stuck in Level 1 or fantasizing about Level 6, this episode has practical, perspective-shifting advice on building wealth—and more importantly, how to enjoy the process without losing your sense of purpose along the way.
Stackers don’t just want to make money—they want to master it without letting it become their master. This conversation bridges income, investing, identity, and intention in a way that gives you both clarity and confidence.
You might even stop worrying about skipping that $5 latte… or realize it’s time to start coding that app you keep talking about at parties.
FULL SHOW NOTES: https://stackingbenjamins.com/invest-differently-and-move-faster-1712
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.
1 hr 15 min

About The Stacking Benjamins Show

From the publisher's feed

Named Best Personal Finance Podcast by Bankrate.com and Kiplinger — and the only podcast the Plutus Awards retired from competition after winning twice — The Stacking Benjamins Show is personal…