Money Unplugged with Chris Hill

In January 2020, Jeff Santoro deposited $50 into a Robinhood account and started buying penny stocks. He had no idea what he was doing. Two months later, the pandemic hit — and he suddenly had a lot of time to figure it out.
Santoro spent 12 years teaching music and has spent the past 13 as a school administrator. He is also the co-host of Investing Unscripted, a podcast he built from scratch (with Jason Hall) after becoming obsessed with investing in his 40s. His path there runs through a false sense of security about his pension, a wife who quietly knew more about money than he did, and a data obsession that started in high school when he was tracking every dollar he spent on Quicken.
Chris Hill talks with Jeff about:
- How having a pension made him dangerously complacent about saving and investing for decades
- Catching both Charlie Munger's last Berkshire Hathaway meeting and Warren Buffett's last as CEO (neither time intentionally)
- The one financial rule he's given his kids that he wishes someone had given him at their age
- Why being “penny wise and pound foolish” is the category of spending he regrets most
What's the last thing you splurged on? Tell us at [email protected].
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Opening clip – “The Big Short”

Brian Feroldi grew up in Rhode Island as a born saver — the kind of kid who hoarded his lunch money candy rather than eating it, just to watch his collection grow. His dad was a CFO. His mom raised money for the ALS Association. Nobody sat him down and explained how investing worked. That part he had to figure out on his own.
A financial educator, YouTuber, and author of the book Why Does the Stock Market Go Up?, Brian joins Chris Hill to talk about the long road from money-illiterate college graduate to one of the most-followed investing educators on the internet. He shares:
- Why he chose his college major purely to save $5,000 a year in tuition — and why the classroom demographics sealed the deal
- How 40,000 miles a year on the road became an unlikely PhD in business and investing, while his coworkers listened to Howard Stern
- What Charlie Munger understood about incentives that most investors still get wrong — and why stock-based compensation at most public companies is completely broken
- Why he regrets his MBA (and it’s not because of the money it cost)

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Opening clip – “Neal Brennan: 3 Mics”

Jason Hall grew up in rural Georgia watching his dad treat money the way most people treat a hot potato — get it and spend it as fast as you can. Nobody talked about saving. Nobody talked about investing. The plan, such as it was, was to fix up a beat-up old truck his grandfather gave him, pulling parts from the junkyard ten miles down the road, and figure the rest out later.
Co-host of the Investing Unscripted podcast and a contributor to The Motley Fool for over a decade, Jason joins Chris Hill to talk about the long, expensive road from that junkyard to genuine financial clarity. He shares:
- Why dropping out of college to sell electronics at Circuit City felt like the smart move — and how money locked him into a career path he never planned on
- The moment his girlfriend's savings account and an unauthorized speaker purchase nearly ended their relationship before it really began
- How he cashed out his 401(k) to pay for a round of golf with two guys whose names he can't remember — and what that decision is worth in today's dollars
- The conversation he had with his wife before walking away from a six-figure sales job to write about investing for half the pay
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Opening clip – “Nate Bargatze: Hello World”

Tyler Gardner grew up eating Cheerios from a bag on a Vermont ski slope while other kids bought hot chocolate. That early lesson about money — absorbed more than taught — sent him on one of the more unconventional paths in personal finance: from stealing grocery money as a kid, to Andover on financial aid, to teaching English at prep schools for a decade, to becoming a financial advisor who thinks most people are asking the wrong question about wealth.
The right question, Gardner argues, isn't how much can I accumulate — it's what do I actually want money to buy? For him, knowing the answer changed everything.
Chris Hill talks with Tyler about:
- Growing up in a household where money was never discussed — and the ski slope memory that first made him realize it mattered
- Attending Andover on financial aid and getting his first glimpse of generational wealth on a spring break trip to Palm Beach
- How a disastrous retirement fund presentation pushed him out of the classroom and into financial advising
- The one thing he wishes he'd understood at 15 that he still has to explain to 60-year-olds today

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Opening clip – “Landman”

Andy Hill hit a million-dollar net worth — and the first thing he did was sell part of his brokerage account and buy a Ford Mustang. It's the kind of decision that makes more sense once you understand how he got there.
The host of the “Marriage Kids and Money” podcast and the author of Own Your Time, Hill grew up in Michigan learning early lessons about saving, investing, and building wealth. Guided by a mother who emphasized frugality and a father who built a career from the ground up, he developed a strong financial foundation — even as investing mistakes and market swings tested his path to financial independence.
Chris Hill (no relation) talks with Andy about:
- Buying a house at 22 with money he'd saved and invested — and why breaking even a decade later still stings
- Falling in and out of love with investing, from tech mutual funds to a WWF stock purchase he'd rather forget
- What he and his wife got wrong about money early in their marriage — and how 16 years later they're still figuring it out
- The one investing move he wishes he'd made earlier — and why it requires almost no skill to pull off

What's the last thing you splurged on? [email protected].
Want to instantly improve your cooking? Go to dizzypigbbq.com and use the promo code “MONEY” to get 10% off your 1st order. 
Opening clip – “Grand Canyon”