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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 there were a way to make charitable giving easier, more strategic, and—dare we say—more satisfying? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Len Penzo welcome Adam Nash, founder and CEO of Daffy, to demystify donor-advised funds. Whether you’ve never heard of them or you’ve been meaning to set one up, Adam walks us through how they work, why they might be a perfect fit for your giving goals, and how they can help you be more intentional with your generosity year-round.

But that’s not all—we also turn the spotlight on an often-overlooked money moment: handling a car insurance claim. From gathering evidence at the scene to negotiating with your insurance company, the team shares smart, practical steps to make sure you don’t leave money (or protection) on the table. And, of course, Len dishes up his trademark personal finance storytelling straight from his new book, mixing in lessons you’ll actually remember with tales you didn’t see coming.

If you’ve been thinking about giving more, protecting yourself better, or just want to walk away with some clever, real-world money moves, this episode’s got you covered. Plus, you’ll leave with an extra nudge to make your charitable giving—and your financial safety net—as strong as possible.

What You’ll Learn in This Episode:

 
The basics of donor-advised funds and how they can supercharge your charitable giving

 
Key differences between donor-advised funds and traditional giving methods

 
How to prepare for and navigate a car insurance claim from start to finish

 
Smart moves for documenting accidents and protecting yourself against disputes

 
Why diversification in your giving can be as valuable as diversification in your investing

 
How Len Penzo turns everyday money lessons into stories you’ll want to retell

Questions to Discuss with Your Fellow Stackers:

 
Have you ever used a donor-advised fund—or would you consider one after hearing this episode?

 
What’s one lesson you’ve learned (the hard way or otherwise) from filing an insurance claim?

 
Do you think giving should be a scheduled part of your financial plan, or something you do more spontaneously?

FULL SHOW NOTES: https://stackingbenjamins.com/donor-advised-fund-deep-dive-1724

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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Donor Advised Funds 101 (with Adam Nash) SB1724

Estate planning might not sound like the most thrilling topic—but skipping it can create a real mess for the people you care about most. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug sit down with attorney Tim Semro to cut through the noise on wills, trusts, and life insurance. Whether you’ve been putting off writing a will or you’re wondering if a trust is worth it, this conversation will give you a clearer path forward.

Tim walks us through the essentials, from the differences between wills and trusts to the sneaky pitfalls that can trip up your beneficiary designations. We also tackle tricky scenarios—like probate headaches, planning across state (or even international) lines, and how to think about life insurance with living benefits. Plus, we swap stories about scams that hit a little too close to home and the simple moves you can take to protect your finances and family.

This episode isn’t about scaring you into action; it’s about showing how estate planning and the right insurance can actually bring peace of mind. By the time you’re done listening, you’ll have a roadmap for protecting your family, making smarter decisions with your money, and avoiding the landmines that could derail your plan. And yes, there’s still a trivia break and plenty of the usual basement flavor to keep things moving.

What You’ll Learn in This Episode:

 
The key differences between wills and trusts—and when you might need each

 
Why beneficiary designations matter more than you think

 
How estate taxes and probate rules can complicate things (and how to prepare)

 
What life insurance with living benefits is—and when it could make sense

 
Red flags for spotting scams and fraud before they hit your wallet

 
How to align your estate plan with your financial and family goals

Questions to Ponder While You Listen (and maybe discuss with us in the Basement Facebook Group):

 
Do you already have a will or trust in place? If not, what’s been holding you back?

 
Have you ever discovered an outdated beneficiary designation (or seen the chaos it caused)?

 
What role do you think life insurance should play in your estate planning?

FULL SHOW NOTES: https://stackingbenjamins.com/estate-planning-charitable-giving-week-1723

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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3 Questions You're Dying To Know about Estate Planning (with attorney Tim Semro) SB1723

Some people chase “work-life balance” like it’s the Holy Grail—spending time, money, and mental energy trying to keep work and personal life perfectly split down the middle. But what if that balance doesn’t actually exist? Live from Joe’s mom’s basement (and not nearly as glamorous as it sounds), Joe Saul-Sehy, OG, Paula Pant, and Jesse Cramer pull back the curtain on whether we should be aiming for balance… or something else entirely.

In this roundtable, the crew wrestles with the difference between work-life balance, alignment, and integration—and why chasing balance might actually keep you from a truly fulfilling life. You’ll hear personal stories, some hard-won lessons about productivity, and a few well-placed digs at Nautica (including the questionable financial moves Joe made in his youth). And because no basement chat is complete without it, we bring you a trivia challenge you didn’t know you needed.

From managing notifications so they stop managing you, to building a life where work and personal priorities don’t compete, this episode digs into the practical steps that help you get more out of both your career and your free time. Whether you’re climbing the corporate ladder, running your own show, or plotting an early retirement, you’ll walk away with tools to rethink how you spend your hours—and why.

What You’ll Learn in This Episode:

 
Why “work-life balance” might be the wrong target—and what to aim for instead

 
The difference between balance, alignment, and integration (and why it matters)

 
Practical ways to keep work from swallowing your personal life whole

 
How to reclaim your attention from constant notifications and distractions

 
Mindset shifts that boost productivity and satisfaction in everyday life

 
Lessons from real-life wins and missteps (including Joe’s Nautica saga)

FULL SHOW NOTES: https://stackingbenjamins.com/all-about-work-life-balance-1722

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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Is Chasing Work-Life Balance Worth the Investment? (SB1722)

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!

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

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!

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

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

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

Man, that time change is always hard. It's getting dark earlier and starting to feel more and more like winter. There's nothing the time change blues can't fix like an episode on managing time and how to make our days feel longer and more efficient. Ashley Whillans joins us to help us work through that never-ending feeling of not having enough time during our day. Where is your time really going? She will help work through that!
Today's episode kicks off another rewind week and you can see our original show notes from 2020, here.
Enjoy!
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Curing Your Time Poverty Problem (w/Ashley Whillans) - REWIND

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