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