The Stacking Benjamins Show
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.
Episodes
March 4, 2026 • 70 mins
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 b...
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March 2, 2026 • 82 mins
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 l...
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February 27, 2026 • 70 mins
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 fin...
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February 25, 2026 • 55 mins
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....
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February 23, 2026 • 60 mins
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. Mo...
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February 20, 2026 • 62 mins
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 focuse...
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February 18, 2026 • 60 mins
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...
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February 16, 2026 • 72 mins
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 ...
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February 13, 2026 • 64 mins
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 ...
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February 11, 2026 • 60 mins
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 ...
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February 9, 2026 • 57 mins
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 ...
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February 6, 2026 • 71 mins
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 ...
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February 4, 2026 • 75 mins
Whitney Elkins-Hutten'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 m...
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February 2, 2026 • 51 mins
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 h...
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January 30, 2026 • 69 mins
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....
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January 28, 2026 • 63 mins
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 a...
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January 26, 2026 • 72 mins
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 Rot...
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January 23, 2026 • 65 mins
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 exp...
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January 21, 2026 • 81 mins
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 ...
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January 19, 2026 • 67 mins
Ever feel like your money questions don't fit neatly into one category? One minute you're thinking about retirement, the next it's insurance, emergency funds, gifting money, or whether your workplace plan is helping or hurting you.
This is one of those episodes where Stackers bring the real-life questions, and Joe Saul-Sehy, CFP Anna Allem, and Neighbor Doug help sort through the noise. It's a true Q&A show built from the issues ...
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