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 info@moneyunpluggedpod.com.
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 – “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)

What is something you bought that makes you happy? Tell us at info@moneyunpluggedpod.com.
Find the best stocks and speed up your investing analysis! Try TIKR for free at tikr.com/unplugged
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
What's the last thing you splurged on? Tell us at info@moneyunpluggedpod.com
Go to ilovemarmar.com and use the promo code “MONEY” to get 10%.
Opening clip – “Nate Bargatze: Hello World”