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PODCAST

The Stacking Benjamins Show

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

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All Episodes

65:02

How One Entrepreneur Constructed a Better Tomorrow...

The Stacking Benjamins Show ·

2025/08/13

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

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62:08

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

The Stacking Benjamins Show ·

2025/08/11

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

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55:26

Hot Financial Takes: Are You In or Out? SB1719

The Stacking Benjamins Show ·

2025/08/08

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,

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76:23

Master the Art of Negotiation with Paula Pant (SB1718)

The Stacking Benjamins Show ·

2025/08/06

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

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81:12

A Sandwich Guide to Navigating Inflation (plus how to...

The Stacking Benjamins Show ·

2025/08/04

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

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66:26

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

The Stacking Benjamins Show ·

2025/08/01

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

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86:45

How to Make Better Decisions Using Math (with Ted...

The Stacking Benjamins Show ·

2025/07/30

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

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53:01

How to Turn 2025's New Tax Rules Into Big Savings...

The Stacking Benjamins Show ·

2025/07/28

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

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63:50

Climbing the Wealth Ladder: Conquering Retirement...

The Stacking Benjamins Show ·

2025/07/25

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

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80:49

Understanding Your Financial Roadmap (with Nick...

The Stacking Benjamins Show ·

2025/07/23

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

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71:29

How to Climb the Wealth Ladder (SB1711)

The Stacking Benjamins Show ·

2025/07/21

What’s the right financial move for you… right now? If you've ever found yourself reading advice meant for a millionaire when you're still trying to crack five figures—or following budgeting tips when your net worth is seven digits—this episode is your custom-tailored financial GPS.In this installment of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Doug take you rung-by-rung through the wealth ladder—from humble beginnings at $10K all the way to $10 million—and explain how your financial

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71:44

How To Waste Your Life (or hopefully, not) SB1710

The Stacking Benjamins Show ·

2025/07/18

Ever feel like you're working hard but getting nowhere? You're not alone—and you might be stuck in a productivity trap, not a purpose-driven plan. In this episode of The Stacking Benjamins Show, we tackle the big one: how to avoid wasting your life. (No pressure.)Joe Saul-Sehy kicks things off with a tongue-in-cheek nod to all the ways we fritter away time—before pivoting into a power-packed conversation on building meaningful goals and avoiding common life derailers. He’s joined by two all-star

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81:29

Create Goals that Stick (with Ret. Lt. Cdr. Gary...

The Stacking Benjamins Show ·

2025/07/16

Want to crush your goals and avoid getting crushed by long-term care costs? In today’s episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Retired Lieutenant Commander Gary McDermott, a former U.S. Navy officer turned business coach, who brings military-grade discipline to the world of goal-setting and financial success.Whether you’re working toward a promotion, launching a side hustle, or just trying to stay on track past February, Gary shares a field-tested,

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80:48

Mid-Year Financial Reset: Key Takeaways from the...

The Stacking Benjamins Show ·

2025/07/14

Still on track to crush your 2025 goals? Or has the year felt more like a Super Mario Kart banana peel moment? In this special mid-year review episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG take a pause from the summer sprint to look back at the most impactful lessons, conversations, and themes from the first half of 2025. Whether you’re rethinking your budget, fine-tuning your risk tolerance, or just trying to remember where you wrote down your resolutions, this is your nudge to hit

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65:06

The Stuff You Should Stop Buying (and Why Your Wallet...

The Stacking Benjamins Show ·

2025/07/11

Is your house full of stuff you thought you needed… but haven’t touched since the Obama administration? In this game show-style episode, we're helping you clean house and bulk up your bank account at the same time.Joining Joe in the basement are Paula Pant from Afford Anything, OG, and the man, the myth, the TikTok-famous legend’s grandpa’s best friend: Len Penzo (or as Doug calls him, “America’s Most Unexpected Influencer”). Together, they go head-to-head in a raucous showdown, each offering hot

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44:51

Happy Money, Hidden Fees, and Hiring Your Kids (SB1706)

The Stacking Benjamins Show ·

2025/07/09

What if your money could bring you more joy—and less stress? Today, we welcome Ken Honda, Japan’s bestselling personal development guru, to the basement. He introduces us to his concept of “Happy Money,” where gratitude replaces fear, and your relationship with money becomes… well, happier. From early lessons in emotional finance to wisdom from his own mentors, Ken shares how small mindset shifts can lead to big life changes.But before we get zen with our Benjamins, Joe and OG shine a light on the

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68:33

Want More Money? Cut The Clutter (with Tracy...

The Stacking Benjamins Show ·

2025/07/07

Is your home packed with emotional baggage... and maybe a few fondue sets you haven’t touched since 2003? Organizational expert Tracy McCubbin joins us to talk about the emotional side of clutter—why it builds up, how it weighs us down, and what to do when your sentimental stuff is quietly running the show.Meanwhile, Joe and OG dig into another kind of mess: the billions retirees lose by claiming Social Security too early. Timing isn’t just everything—it’s the difference between thriving in

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68:06

Let's Start a Money Revolution (SB1704)

The Stacking Benjamins Show ·

2025/07/04

Happy Independence Day, Stackers! While fireworks boom and flags wave, we're lighting a spark under your financial life. This episode isn’t about tea in harbors—it’s about burning down debt, revolting against lifestyle creep, and rallying your family for a better money future. Joining Joe and Doug in the basement for this full-on financial insurrection: Dorethia Kelly, TikTok titan and money coach, shares how she raised her financial flag as a single mom and became a force for smart money

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71:34

Turning Ideas into Billion Dollar Businesses (with...

The Stacking Benjamins Show ·

2025/07/02

What does it take to turn a bold idea into a billion-dollar brand? Julie Wainwright, founder of The RealReal, joins us to share how she did just that—after enduring some pretty public failures (hello, Pets.com). She talks about navigating the startup world, tackling ageism head-on, and why your past doesn’t define your future.Julie’s story is packed with wisdom on risk-taking, confidence, and what it really means to build something new when everyone else is telling you no. From the boardroom to

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57:37

Is the 4% Rule In Play? (SB1702)

The Stacking Benjamins Show ·

2025/06/30

How much can you really spend in retirement without running out of money—or worse, running out of fun? In this deeper-than-usual dive, Joe Saul-Sehy and OG examine the classic 4% retirement rule and whether it’s time for an upgrade. With new commentary from Bill Bengen, the original architect of the 4% rule, the team explores emerging research that suggests a withdrawal rate closer to 5.5% might be possible—if you’ve got the right mix of investments, a solid plan, and a bit of courage. But we

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