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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 happens when you hand the mic to Stackers? You get a mailbag episode loaded with real-life money challenges, surprising lessons, and a few “wait, what?” moments. Joe Saul-Sehy, OG, special guest Anna Allem (a CFP® with her own winding journey into the profession), and Neighbor Doug dig into your most pressing financial questions—no fluff, no jargon, and definitely no shortage of basement-style tangents.

This week’s listener lineup serves up a buffet of topics: how to turn an HSA into a stealth retirement account, whether a Roth conversion is the right move (and when), the tricky little details that make or break a trust, and what’s happening in the ever-shifting world of auto insurance. Along the way, we get into the mental game of money—why positive thinking might be more than motivational fluff—and how planning isn’t just about the plan on paper.

From Anna’s seasoned perspective to OG’s no-nonsense approach and Joe’s knack for cutting through the noise, you’ll walk away with strategies you can actually use. Plus, we can’t resist a detour into AI at the Wendy’s drive-thru (yes, it’s a thing), proving once again that money talk is always better when you leave room for curiosity.

What You'll Learn This Episode:

 
How to decide if a Roth conversion makes sense for your tax picture

 
Ways to supercharge an HSA for long-term wealth (and not just medical expenses)

 
Trust basics you might be overlooking—and why that could cost you.

The latest trends in auto insurance and how they might affect your rates

Why mindset matters just as much as math in building financial confidence

Questions to Ponder (or Argue Over in the Basement)

 
If you were starting an HSA today, how would you use it—medical safety net or stealth retirement account?

 
Have you considered a Roth conversion? What’s the one factor holding you back?

 
When it comes to trusts, do you prefer to keep heirs in the loop or keep plans private until needed?

 
How do you decide when to update your insurance coverage versus just shopping for a better rate?

FULL SHOW NOTES: https://stackingbenjamins.com/questions-from-the-stacker-community-1730

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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We Answer Your Awesome Questions: HSAs, Roth Conversions, Trusts, and More (SB1730)

Labor Day might be about rest, but in the basement, we’re getting to work on busting some of the most persistent myths in personal finance. Joe Saul-Sehy and OG welcome insurance pro Tony Steuer to unpack the shiny marketing around infinite banking and velocity banking. Spoiler: sometimes “be your own bank” really means “make your insurer rich.” From permanent life insurance pitfalls to the real math behind these strategies, Tony helps separate clever sales pitches from solid financial planning.

Then we shift gears to a conversation every parent, grandparent, and future gift-giver will love. Renowned financial journalist Chuck Jaffe joins the crew, fresh from becoming a grandfather, to share how he’s setting his new grandchild up for a strong financial future. Think stock portfolios for toddlers, early Roth IRA strategies, and simple systems that keep family generosity from getting lost in the shuffle. His practical, battle-tested tips will have you thinking differently about the best ways to give kids a head start.

Whether you’re looking to avoid costly detours or create generational wealth, this episode is equal parts cautionary tale and inspiration. You’ll walk away ready to dodge financial traps, build smarter for the next generation, and maybe even rethink your own long-term giving plans.

 
Why infinite and velocity banking aren’t the slam-dunk solutions they’re often sold as

 
How to spot the red flags in permanent life insurance pitches

 
Smart, tax-efficient ways to save for children and grandchildren

 
Creative strategies for gifting assets that grow with the child

 
The importance of balancing generosity with your own long-term goals

Ideas to Ponder During Today's Episode

 
Have you ever been pitched an “innovative” financial strategy that didn’t feel quite right? What tipped you off?

 
What’s the most meaningful financial gift you’ve ever given—or received—as a child?

 
If you could give one piece of financial wisdom to the next generation, what would it be?

FULL SHOW NOTES: https://stackingbenjamins.com/permament-life-insurance-and-growing-your-money-1729

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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Unpacking Two Big Ideas: Infinite Banking and Saving For Young Children (SB1729)

Why wait until your knees creak louder than your rocking chair to start enjoying life? In this episode, Joe Saul-Sehy, OG, Paula Pant (AffordAnything) and Neighbor Doug welcome Jillian Johnsrud—author of Retire Often—to share why sprinkling your life with mini-retirements might be the smartest, healthiest, and most joyful move you make before your “official” retirement date. Think of it as giving your future self a head start… without the Medicare paperwork.

From negotiating time off without burning bridges, to building a financial plan that lets you step away without panic, Jillian offers a roadmap to hit pause on your career without pressing stop. We explore the balance between health, capability, and the freedom to explore, and how to sell the idea of a mini-retirement to your boss so they don’t see it as a resignation letter in disguise. And because it’s the basement, we also mix in some Labor Day trivia, a few personal experiments with unconventional choices, and just enough playful banter to keep you leaning in.

If you’ve ever felt the grind wearing you down but can’t picture walking away forever, this episode will help you reimagine your work-life timeline. Mini-retirements aren’t just for the wealthy or the whimsical—they’re for anyone ready to start living a retirement-worthy life now.

 
How to pitch a mini-retirement to your boss without triggering an awkward HR meeting

 
The financial prep work that makes time off less stressful and more satisfying

 
Ways to test-drive retirement before the “official” date

 
How to handle the skeptics (at work and at home) who think you’re making a mistake

 
Why health and capability should be part of your retirement timing equation

Questions to Ponder While You Listen

 
If you could take 3–6 months off tomorrow, how would you spend it?

 
Would a series of shorter retirements feel more fulfilling than one long one at the end?

 
What’s the biggest barrier—financial or otherwise—keeping you from taking a break?

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How To Tell Your Boss You Want to Retire Often (SB1728)

If you’ve been running on fumes, juggling work deadlines, family obligations, and maybe even a neglected 401(k) or two, this episode is your permission slip to stop, breathe, and recalibrate. Joe Saul-Sehy, OG, and Neighbor Doug welcome Dr. Danielle McGeough—professor, transformational strategist, and champion of intentional living—into the basement for a conversation that’s part burnout intervention, part life strategy workshop.

Dr. McGeough shares how to spot the early signs of burnout before you hit the wall, and how to rebuild your days with personal rituals, playfulness, and values-driven planning. You’ll hear real-world strategies for setting boundaries, aligning work with what truly matters to you, and bringing joy back into your calendar. And because we’re in the basement, we also manage to sneak in some Labor Day trivia, a Broadway tangent, and a solid helping of SB-style banter.

And for the Stackers worried about the financial side of burnout, we pivot in the second half to a practical discussion on managing multiple 401(k) plans—because a cluttered retirement portfolio can be just as stressful as a cluttered schedule. From account consolidation tips to understanding your investment options, this is a one-two punch of mental clarity and financial order.

 
How to recognize the red flags of burnout (and stop it in its tracks)

 
Why personal rituals and play can fuel productivity and joy

 
How to align your schedule with your core values

 
Strategies for balancing ambition with sustainability

 
Practical steps for managing multiple 401(k) plans without losing track

 
Why decluttering your finances can boost your mental clarity

Thoughts to Ponder During the Episode

 
What’s one personal ritual you could add to your day that would give you energy instead of draining it?

 
Have you ever consolidated old retirement accounts? What made you decide to do it (or not)?

 
How do you know when you’ve hit your “enough” point with work and need to reset?

 
What’s one value you’d like to see reflected more clearly in your daily life?

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-reset-with-clarity-and-purpose-1727

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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Dr. Danielle McGeough's Guide to Avoiding Burnout (SB1727)

Ever think, “If I just followed the playbook of the ultra-wealthy, I’d be set for life”? Turns out, that’s exactly the kind of thinking that can lead you straight into the arms of a scammer. In this episode, Joe Saul-Sehy and OG break down the traps hidden inside the “invest like the 1%” mantra (and other similar phrases), complete with real-life cautionary tales, including a small-town Ponzi scheme that could’ve been ripped from a Netflix docuseries, and the spectacular belly flop of some YieldStreet real estate bets.

But it’s not all doom and gloom in the basement. You’ll also get the scoop on a controversial proposal to let private equity sneak into your 401(k), practical tips for spotting shady pitches before they drain your wallet, and the reminder that a boring-but-solid financial plan beats a flashy scam every time. Plus, the guys field a listener question on long-term care insurance and unpack the often-overlooked basics of HSAs.

Between headlines, trivia detours, and a dash of movie talk, this episode arms you with the street smarts to dodge the next “too good to be true” investment opportunity. It’s a masterclass in protecting your money—without having to hide it under your mattress.

 
The psychological tricks scammers use to lure in even savvy investors

 
Why “invest like the 1%” can backfire for everyday Stackers

 
How to evaluate alternative investments (and when to walk away)

 
The risks and realities of adding private equity to retirement accounts

 
Key questions to ask before buying long-term care insurance

 
Why a strong, clear financial plan is your best defense against cons

Questions to Ponder During Today's Show:

 
Have you ever been tempted by an investment pitch that felt “exclusive”?

 
Would you want private equity options inside your 401(k)? Why or why not?

 
How do you decide whether an alternative investment is worth the risk?

 
What’s your personal “red flag” that makes you walk away from a deal?

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-avoid-common-rip-offs-1726

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 Deceptive Allure of Investing Like the 1% (How We Get Conned) SB1726

If you’ve ever wondered whether you should pass on your money now or make your heirs wait for the “big reveal” (cue the dramatic reading of your will), this is your episode. Joe Saul-Sehy, OG, and Neighbor Doug welcome Paula Pant from Afford Anything and Jesse Cramer from Personal Finance for Long-Term Investors to play a high-stakes round of “In or Out” with estate planning and charitable giving. Is anonymous giving a waste of good publicity? Should you set up a donor-advised fund or keep it simple? Is sharing your estate plan with your heirs wise—or an invitation to awkward holiday dinners?

This isn’t your average dry legal seminar. Between football analogies, dinosaur jokes, and the occasional jab at Ford’s electric truck sales, our crew digs into the real-life choices Stackers face when deciding how—and when—to pass along their wealth. You’ll hear hot takes, smart strategies, and maybe even a nudge to start that conversation you’ve been putting off.

From the practical (avoiding probate, maximizing giving impact) to the philosophical (why give at all, and how much?), this episode blends useful tactics with the irreverent basement energy you know and love. It’s part money talk, part game show, and 100% designed to get you thinking about your financial legacy.

 
The pros and cons of giving now versus after you’re gone

 
How donor-advised funds work and whether they’re worth your time

 
Why anonymous giving might be overrated—or a hidden superpower

 
Ways to avoid family drama by (maybe) sharing your estate plan early

 
How to think about charitable giving as part of your overall financial plan

Questions to ponder during the show:

 
Would you rather give now and see the impact, or give later and leave a surprise?

 
How much transparency do you think heirs deserve about your estate plans?

 
If you give anonymously, are you missing an opportunity—or dodging a headache?

 
What would you want your charitable legacy to look like?

FULL SHOW NOTES: https://stackingbenjamins.com/estate-planning-giving-week-in-or-out-1725

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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Estate Planning, Charitable Giving, and Financial Hot Takes (SB1725)

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!

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

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

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!

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

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

How are you with cash? Credit? Putting money in investments? All of that begins with your mindset, and Jen Sincero joins us today to help you get your head in the right place.
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You Can Be a Badass With Money

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