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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

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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How One Entrepreneur Constructed a Better Tomorrow (with Cheryl McKissick Daniel) SB1721

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

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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Hot Financial Takes: Are You In or Out? SB1719

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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Master the Art of Negotiation with Paula Pant (SB1718)

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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A Sandwich Guide to Navigating Inflation (plus how to plug 401k "leakage") SB1717

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

What Would YOU Do With $50,000? (SB1716)

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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How to Make Better Decisions Using Math (with Ted Dintersmith) SB1715

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

How to Turn 2025's New Tax Rules Into Big Savings (SB1714)

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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Climbing the Wealth Ladder: Conquering Retirement Fears (with Mark Trautman) SB1713

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

Understanding Your Financial Roadmap (with Nick Maggiulli) SB1712

Our good friend Ben Franklin said the only things certain in life are death and taxes. Since we are coming up on year-end, we'll tackle one of those certainties (you're on your own with the other). To help us, tax expert Ed Slott is back! He'll help you get your finances in order before year-end to avoid any tax surprises in April. Should you convert your IRA to a Roth? What's the contribution deadline for retirement accounts? What changes might be coming in future legislation? Ed's commenting on it all with us today.
We'll also talk about regulation in cryptocurrency during our headline segment. One of the main benefits of cryptocurrency has been the idea that it is unregulated, but the U.S. government is trying to change that. Although the SEC can't agree, will they consider crypto a security and therefore have regulation over it? We'll share the latest details! We'll also tackle 529 and college saving plans during our Haven Lifeline.
Enjoy!
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Your 2021 Year-End Tax Planning Guide (with Ed Slott)

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