How a Music Teacher Went From $50 on Robinhood to Hosting an Investing Podcast (Jeff Santoro)

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”