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PODCAST

The Stacking Benjamins Show

StackingBenjamins.com | Money Podcast | 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

69:52

Even the Pros Are Wrong Half the Time. Here's What...

The Stacking Benjamins Show ·

2026/03/25

The best investors in the world are wrong -- a lot. Researchers Claire Flynn Levy and Lee Freeman-Shor spent over a decade studying elite money managers and found that being right about stock picks isn't actually what separates the winners. What separates them is what happens after the pick. The discipline, the rules, the willingness to act when the data changes -- and the ability to remove emotion from decisions most people make entirely on feeling.What You'll Walk Away With Why top investors

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65:31

The Real Return on Your Emergency Fund Has Nothing to...

The Stacking Benjamins Show ·

2026/03/23

If your emergency fund feels like it's just sitting there doing nothing, you might be measuring the wrong thing. The real return on cash isn't the yield -- it's what that cash helps you avoid. Panic selling during a downturn. High-interest debt after an unexpected bill. Tapping your 401(k) at exactly the wrong moment. Joe and OG reframe emergency savings not as a financial placeholder, but as a strategic asset quietly holding your entire plan together. What You'll Walk Away With Why your

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70:23

How to Build a Financial Plan That Holds Up When Life...

The Stacking Benjamins Show ·

2026/03/20

Your financial plan is only as good as what happens to it under pressure.A market drop. A job loss. An inflation spike that turns "fine" into "wait, what?" Most portfolios are quietly optimized for the good times, and that's exactly why they crack when things get uncomfortable. This week, Joe, Paula, Jesse, and special guest Paul Merriman aren't chasing the highest returns. They're building for something harder: a system that doesn't force bad decisions when everything around it is going

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58:36

What to Build After You Hit "The Retirement Number"...

The Stacking Benjamins Show ·

2026/03/18

What if reaching financial independence was the easy part?Amy Minkley spent years optimizing toward her number — then hit it and discovered something nobody's spreadsheet prepares you for: freedom without purpose feels surprisingly empty. She joins Joe and OG to talk about what actually fills the gap: community, meaning, and building something instead of just escaping something. Then the basement crew gets practical. Because even the most purpose-driven life still needs its foundations. Joe and

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72:27

The One About 401k Loans (and How To Stay Away From...

The Stacking Benjamins Show ·

2026/03/16

A 401(k) loan often looks harmless. You're borrowing from yourself, the interest comes back to you, and you'll pay it back before it matters -- right? But the fastest way to protect your retirement isn't understanding how loans and hardship withdrawals work. It's building a financial life where you almost never need them. Joe and OG dig into why more people are tapping retirement accounts than ever, and what confident investors quietly do differently. What You'll Walk Away With Why the biggest

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71:13

Why Doing Less With Your Money Is the New Investing...

The Stacking Benjamins Show ·

2026/03/13

Millennials didn't just change how people invest -- they changed what investing even looks like. Cheaper, faster, more automated, and occasionally more dangerous than anything that came before. The real question isn't whether to adopt their habits. It's which ones are actually building wealth and which ones are quietly lighting your portfolio on fire. Joe, OG, Jen Smith (Frugal Friends), and Doc G (Earn & Invest) sort the signal from the noise.What You'll Walk Away With The quiet Millennial

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61:42

When Money Rules Don't Match Real Life (Your...

The Stacking Benjamins Show ·

2026/03/11

Personal finance loves clean rules. Save 20%. Follow the 4% rule. Always max the 401(k). But real life rarely cooperates with tidy formulas.This week Joe Saul-Sehy, OG, and guest co-host CFP Anna Allem dig into the gap between the advice we hear and the messy decisions we actually face. What your savings rate really means. How often you should rethink inflation assumptions. Why a mysterious tax form after a backdoor Roth conversion might not be the crisis it first appears to be. Turns out some of

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57:53

Private Equity for Regular People: Higher Returns or...

The Stacking Benjamins Show ·

2026/03/09

The ultra-wealthy get access to private equity, private credit, and pre-IPO deals the rest of us don't. Now, suddenly, those same deals are being marketed to you. Coincidence? Maybe. Cause for suspicion? Absolutely. Joe, OG, and Doug settle in at the basement desk (yes, Joe's mom's basement — the most prestigious financial address in podcasting) to dig into a Wall Street Journal headline asking whether everyday investors should be chasing the same private deals as the 1%. OG breaks down why

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49:12

Should You Invest When the Market Feels Too High? SB1812

The Stacking Benjamins Show ·

2026/03/06

The market feels expensive. Again. So should you invest or wait for a pullback?Joe Saul-Sehy brings together a powerhouse roundtable featuring Len Penzo, Paula Pant (Afford Anything), and Greg McFarlane to tackle the question every investor faces when markets hit new highs. The twist? This conversation originally happened in 2016 when the SPY ETF which tracks the S&P 500 was trading at around $190. Today it's near $700. Everyone who waited for the "right time" back then missed massive gains

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70:49

Around the World in 80 Days: The Travel Mindset That...

The Stacking Benjamins Show ·

2026/03/04

What if retirement isn't about doing less, but about becoming more?George Jerjian spent his career as a retirement mindset coach, helping others navigate life after work. Then he decided to practice what he preached. He planned an 80-day round-the-world journey, intentionally choosing unfamiliar countries where he'd be forced out of his comfort zone and into transformation. This greatest hits crossover from Stacking Adventures brings George's story to the basement, not because it's about exotic

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82:36

Building Courage One Small Step at a Time SB1810

The Stacking Benjamins Show ·

2026/03/02

If Jen Drummond can climb K2, you can open that Roth IRA. That's the premise of this greatest hits episode featuring mountaineer and author Jen Drummond, who became the first woman to complete the Seven Second Summits. But here's why we're replaying this conversation from early 2024: it's not about mountaineering. It's about courage. Joe Saul-Sehy opens by explaining why courage matters for your money goals. It takes courage to look at your financial life honestly, to try something new like

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70:59

You Don't Need to Be a Money Genius to Win SB1809

The Stacking Benjamins Show ·

2026/02/27

Live from Joe's mom's basement (where humility is encouraged and spreadsheets are optional), the crew tackles a deceptively simple question. If most people think they're above average with money, what advice actually helps someone who isn't?Joe Saul-Sehy, OG, Doug, Jesse Cramer, and guest Whitney Hanson (Money Nerds podcast) run a thought experiment inspired by Morgan Housel's observation that nearly everyone believes they're financially smarter than the median. What straightforward moves keep

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55:25

How She Eliminated a $43,000 Hospital Bill (SB1808)

The Stacking Benjamins Show ·

2026/02/25

Live from Joe's mom's basement (where the jokes are free but hospital care apparently isn't), the Stacking Benjamins crew tackles two very real financial stressors: surprise medical debt and a shifting housing market.First up is Imani Vance, who joined the Coast Guard at 19 and soon faced a nightmare scenario. What started as appendicitis escalated to severe sepsis after limited on-base resources and long waits for off-base care. After hospitalization, including treatment for an abscess and

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60:20

Suze Orman Changes Her Mind on Working to 70 (SB1807)

The Stacking Benjamins Show ·

2026/02/23

Live from Joe's mom's basement (complete with dog mugs, birthday roasting, and Doug polishing his trivia crown), the crew tackles a headline that caught plenty of attention. Suze Orman backing off her long held stance that everyone should work until age 70.Does that mean you shouldn't work longer? Not exactly. Joe Saul-Sehy, OG, Doug, and special guest Len Penzo break down the math behind working into your late 60s or beyond. More years to save, more compounding, fewer years drawing down assets

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62:49

How to Talk to Kids About Money (Without Making It...

The Stacking Benjamins Show ·

2026/02/20

Want your kids to grow into confident money decision-makers without turning every dinner conversation into a financial lecture? In this roundtable episode, Joe sits down with Livia (“Liv”) Roder, host of the Liv Lab Podcast, Karen Holland of GiftingSense.org, and John Lanza, host of the Art of Allowance Podcast to explore what actually helps kids understand money before the stakes get big.Instead of theory, this discussion focuses on real moments when money suddenly becomes real: college price

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58:19

Best Tax Software for 2026 (And Handling Market...

The Stacking Benjamins Show ·

2026/02/18

Live from Joe's mom's basement (where receipts go to be judged and spreadsheets fear OG), this episode tackles two big questions Stackers are asking right now. What's the best tax software for filing your 2025 return? And what should normal, long term investors make of gold, silver, and crypto taking a wild ride?Joe Saul-Sehy and OG are joined by Robert Farrington from The College Investor to break down the tax software landscape without the marketing fluff. Because if you're our Stacker avatar,

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72:20

The Boring Plan That Built $2 Million SB1804

The Stacking Benjamins Show ·

2026/02/16

Think building seven figure wealth requires exotic investments or perfect timing? This President's Day episode from Joe's mom's basement tells a very different story. Joe Saul-Sehy, OG, and Neighbor Doug dig into a Kiplinger My First Million case study featuring a Wisconsin couple who started saving at age 32 with exactly zero invested and quietly built $2 million over the next 22 years using mostly retirement accounts and steady habits. Their success sparks a bigger conversation about why simple

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62:03

Love It or Leave It: Financial Edition (SB1803)

The Stacking Benjamins Show ·

2026/02/13

Nothing says romance like a heated debate about the 4% rule.Live from the basement (which suspiciously resembles YouTube headquarters), Joe Saul-Sehy, OG, Neighbor Doug, and the panel celebrate Valentine's Day weekend the only way Stackers know how: by putting their favorite financial ideas on the hot seat. This isn't a polite discussion. It's a rapid fire "love it or leave it" showdown where popular money strategies either get roses or get shown the door. On the chopping block: Paying off a

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60:39

How to Talk About Money Without Fighting SB1802

The Stacking Benjamins Show ·

2026/02/11

What's more romantic than roses and chocolate? How about not fighting about money.Joe Saul-Sehy and OG welcome Douglas and Heather Boneparth, the financial planning power couple who literally wrote the book on navigating money in relationships. Broadcasting from the basement (where love is patient and spreadsheets are kind), the crew dives into how people can build financial trust, avoid money secrets, and actually enjoy talking about dollars without it turning into a heavyweight title

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57:09

Are You Investing or Just Placing Bets? SB1801

The Stacking Benjamins Show ·

2026/02/09

Joe Saul-Sehy, OG, and Neighbor Doug pull up a rickety basement chair and unpack a growing trend: people treating investing like a series of high stakes bets instead of a long term plan. Sparked by a recent Wall Street Journal piece on aggressive investing, the gang digs into where the line is between smart risk taking and straight up gambling with your future. Using plenty of real world examples and a few basement metaphors, the crew breaks down how stocks, businesses, options, and even so-called

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1,451 results

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