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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

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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71:06

The Worst Money Advice Ever (Episode 1800!)

The Stacking Benjamins Show ·

2026/02/06

Eighteen hundred episodes calls for something special, and what better way to celebrate than by dragging the absolute worst money advice into the light and laughing at it together?Special guest and CFP Sarah Catherine Guiterrez from Aptus Financial joins Joe Saul-Sehy, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) for a rapid-fire, no mercy takedown of the most damaging financial clichés ever passed down at family dinners, car

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75:26

Building a Wealth Machine That Lasts Generations...

The Stacking Benjamins Show ·

2026/02/04

Whitney Elkins-Hutton's story isn't about overnight success or getting lucky. It's about building a wealth machine that keeps working even when life throws curveballs.Broadcast as always from Joe's mom's basement, this episode explores how Whitney went from a modest, very 1970s upbringing to creating systems that generate lasting wealth, and what everyday people can realistically take from her experience. Yes, she built an $800 million real estate portfolio, but this conversation is about

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51:58

Stop Leaving Money on the Table at Tax Time (SB1798)

The Stacking Benjamins Show ·

2026/02/02

Taxes don't have to feel like something that happens to you. Joe Saul-Sehy, OG, and Neighbor Doug break down the biggest recent tax changes and, more importantly, how to use them intentionally instead of accidentally leaving money on the table. This isn't about memorizing the tax code or becoming a DIY CPA. It's about understanding where the real opportunities are right now, which moves matter most at different life stages, and how smart planning today can quietly add up to thousands of dollars

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69:17

How to Get 1% Better Without Burning Out (SB1797)

The Stacking Benjamins Show ·

2026/01/30

What if the path to better money decisions, more confidence, and a calmer life wasn't a massive overhaul but just getting a tiny bit better today than you were yesterday?Joe Saul-Sehy, Neighbor Doug, OG, and Paula Pant (Afford Anything) are joined by David Gillis, creator of the 1% Better Conference, for a roundtable exploring the surprisingly powerful idea of improving by just 1% at a time. No vision boards. No 5 a.m. ice baths. Just small, intentional choices that compound into real results,

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63:24

The Science of Better Ideas with George Newman

The Stacking Benjamins Show ·

2026/01/28

Where do great ideas come from, and why do they always show up in the shower, on a walk, or five minutes after you've stopped trying so hard?Joe Saul-Sehy, OG, and Neighbor Doug welcome this week's mentor, behavioral scientist George Newman, to unpack how creativity really works and how Stackers can use it to make better decisions with money, careers, and life. This isn't about becoming "more creative" in a woo-woo sense. It's about understanding the conditions that consistently produce better

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72:32

When to Trust Your Gut and When to Trust the Math SB1795

The Stacking Benjamins Show ·

2026/01/26

Ever made a money move that felt right then immediately wondered if you just emotionally invested in a bad idea? We've all done it. Some of us have receipts. Joe Saul-Sehy, OG, and Neighbor Doug tackle one of the trickiest parts of personal finance: knowing when to trust your gut and when your gut needs to sit down and let the math speak. Because here's the thing. Most Stackers aren't struggling because they don't know what a Roth IRA is. You're struggling because real life decisions don't happen

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65:30

How to Afford Life Without Living Like a Monk (SB1794)

The Stacking Benjamins Show ·

2026/01/23

Inflation may be doing its best to body slam your budget, but this episode is all about fighting back without turning your life into a sad spreadsheet. Joe Saul-Sehy, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) are joined by special guest Justin Brown-Woods (Price of Avocado Toast) for a roundtable tackling the big question Stackers keep asking: Why does life feel so expensive even when I'm doing everything right? Instead of the usual

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81:36

How to Make Your Money Support the Life You Want...

The Stacking Benjamins Show ·

2026/01/21

What if your money stopped dictating your schedule and started supporting the life you actually want to live?Joe Saul-Sehy welcomes CFP Dana Anspach of Sensible Money as special guest co-host for an episode featuring this week's mentor, Andy Hill. Andy shares how he stepped away from the corporate grind, redesigned his priorities, and built a life where family and flexibility came first. His story isn't about escaping work. It's about building a financial foundation that gives you options. Then

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1,443 results

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