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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 can you learn about leadership from someone who’s served four U.S. Presidents, navigated some of the most intense moments in American politics, and still believes the future depends on building more leaders, not fewer? In this Greatest Hits Week replay, Joe Saul-Sehy, OG, and Neighbor Doug welcome David Gergen—former White House advisor, Harvard professor, and author—to the basement for a masterclass on leadership that applies as much to your career and investments as it does to running a country.

Gergen pulls back the curtain on life inside the White House, from the early lessons he learned in the Navy to the behind-the-scenes moments that revealed the human side of Presidents. Along the way, he shares what separates great leaders from the rest, how to evaluate leadership in others (and yourself), and why service and responsibility are the cornerstones of lasting influence. Whether you’re leading a team at work, managing your family’s financial future, or just trying to be the kind of person others trust, you’ll find plenty here to sharpen your approach.

And because no visit to the basement is complete without some SB-style surprises, you’ll also hear stories of presidential humor gone sideways, a White House prank or two, and reflections on how good leadership isn’t about perfection—it’s about purpose. Plus, the guys tackle a listener question on investing without specific goals, and Doug tests the panel’s trivia chops with a leadership twist.

What You’ll Learn in This Episode:

 
How David Gergen defines real leadership (and how it’s changed over time)

 
The telltale signs you’re working with—or for—a great leader

 
Lessons from the Navy, the West Wing, and history’s most memorable leaders

 
Why building leaders is just as important as being one

 
Practical ways to evaluate leadership in politics, business, and investing

 
How a clear sense of service can make you a better investor and decision-maker

Questions for you while you listen (share with our Facebook group!):

 
Who’s the best leader you’ve ever worked for, and what made them stand out?

 
How do you evaluate whether someone is worth following—whether in politics, business, or life?

 
What’s one leadership skill you wish more people would develop?

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How to Lead (and Evaluate Good Leadership) with David Gergen (SB1733)

Not all financial advisors are created equal—and some will steer you straight into the rocks while smiling the whole way. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug share the top five warning signs your advisor may not have your best interests at heart. From shady investment recommendations to fee structures that deserve a magnifying glass, we unpack the behaviors and practices that can quietly drain your portfolio.

This isn’t just about avoiding bad actors—it’s about knowing what great advice looks like so you can spot the difference. You’ll hear why “fun money” accounts can be a trap, how to sniff out overly speculative pitches, and why transparency isn’t optional when it comes to your financial future. Along the way, we sprinkle in a few stories, historical nuggets, and plenty of those classic “Doug moments” that make a trip to the basement worth your time.

If you’ve ever wondered whether your financial guide is truly on your side—or if you just want to sharpen your radar—this episode will give you the practical tools to tell the difference between a trusted partner and a wolf in a well-tailored suit.

What You’ll Learn in This Episode

 
The five biggest advisor red flags that should send you running

 
How to evaluate an advisor’s investment recommendations for risk and suitability

 
Why fee transparency can make or break a relationship

 
The subtle clues in an advisor’s office environment and interactions

 
The difference between fun money accounts and dangerous speculation

 
How to ensure your advisor’s plan matches your long-term goals

Questions to Think About:

 
When’s the last time you reviewed exactly how your advisor gets paid?

 
Are you clear on the why behind each investment they’ve recommended?

 
Would you feel confident explaining your advisor’s strategy to a friend—or does it sound like a foreign language?

This episode originally aired on August 2, 2023. Please disregard any mention of current events. You can find the original show notes here.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-spot-a-subpar-advisor-greatest-hits-week-1732

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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Spotting the Sharks: 5 Red Flags Your Financial Advisor Might Be Waving (SB1732)

Ever celebrate paying off a credit card…only to watch your credit score drop? Or ditch your budget for “simplicity” and find yourself ordering takeout three nights in a row? On this week’s episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome Paula Pant (Afford Anything) and Jesse Cramer (Personal Finance for Long-Term Investors) to explore why even the “right” financial moves can sometimes lead you straight into a banana peel.

From the hidden traps of credit scores and debt freedom to the way a shiny new credit card reward program can cost you more than you bargained for, this roundtable digs into the ripple effects that don’t make the brochure. We’ll tackle when “optimizing” your plan goes too far, how well-meaning programs can backfire, and why the metric you’re tracking might not be the one that actually matters.

Expect sharp insights, lively debate, and tips you can put into action—without getting tangled in the very strategies meant to help you. Because money confidence isn’t just about making the right moves…it’s about knowing what those moves might do next.

We'll Cover:

 
Why your credit score might drop after paying off debt—and why that’s not always bad news

 
How “budget hacks” can turn into budget headaches

 
The sneaky ways credit card rewards and government programs can backfire

 
Why tracking the wrong measure can lead to the wrong results

 
Practical steps to sidestep the unintended fallout from good decisions

Questions to Ponder During the Episode

 
What’s the most surprising “side effect” you’ve experienced after making a smart money move?

 
Have you ever optimized your budget or investment plan…only to regret it?

 
Which metric do you track most closely in your financial life—and is it actually the right one?

FULL SHOW NOTES: https://stackingbenjamins.com/unintended-credit-score-consequences-1732

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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Outsmarting Unintended Consequences: How Good Money Moves Don’t Go as Planned (SB1731)

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

Discussing finances can be intimidating, especially for beginners. However, initiating regular money conversations early on can be a great way to introduce the topic and potentially set yourself up for financial success. In today's roundtable, we welcome Dan Sheeks, author of the new hit book, First to a Million: A Beginner's Guide to Achieving Early Financial Independence, Katie Brewer, a certified financial planner and professional money teacher, and OG, our in-house money expert and father of three. They will discuss the importance of having money conversations and provide tips on how to set yourself up for a life of financial abundance.
But wait! There's more! Doug will try to stump our panel with some this-day-in-history-based trivia. It's a tie ballgame in our year-long competition; who will pull ahead?
FULL SHOW NOTES: https://www.stackingbenjamins.com/dan-sheeks-1328
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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Smart Money Moves: Building Financial Habits That Last a Lifetime

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