Dan Caplinger has spent most of his career helping people understand money — first as a tax and estate planning attorney, then as a longtime writer at The Motley Fool. But the financial lessons that shaped him most started long before any of that: skipping school lunch to save a few dollars, counting coin rolls with his mom, and learning the hard way that a $60 Pac-Man game isn't what a nine-year-old thinks it is.
Chris Hill talks with Dan about:
- What the billable-hours model of law firms taught him about misaligned incentives
- How he and his wife structured their finances before getting married
- One change he would make to the US tax code
- The money lesson he wishes he'd learned at 19
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What's your favorite movie or TV series about money? Tell us at info@moneyunpluggedpod.com.
Opening clip – “Wall Street”

What if the stocks you believe in the most are the ones you actually own? Brian Stoffel spent years as a teacher before stumbling into investing — and one experiment changed everything. After reading Nassim Taleb's Skin in the Game, he went back and coded 300 of his own articles into two buckets: companies he wrote about positively that he owned, and companies he wrote about positively that he didn't. The results were striking. The stocks he owned outperformed the market. The ones he didn't own underperformed — by a wide margin.
Brian talks with Chris Hill about what that experiment taught him about conviction investing, why he looks for companies that get stronger under stress, and what his unconventional path (from rural Iowa to DC classrooms to Costa Rica) taught him about the relationship between money and the things that actually matter in life, as well as:
- The reason he actively avoided money for most of his early life
- A mistake with whole life insurance he made as a 1st-year teacher
- What Nassim Taleb and a small Iowa college basketball team have in common
- Why he doesn’t “fight the universe”
Find more from Brian at LongTermMindset.co
What’s your favorite movie or TV series about money? Tell us at info@moneyunpluggedpod.com
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Opening clip – “Heist”

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.
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Opening clip – “The Big Short”