Episode Details

Chris Mayer, author of 100 Baggers and The Investor's Odyssey, on what three years on a public company board taught him, how he uses AI as a junior analyst, and what he actually does when a position gets cut in half. Stick around after the goodbye, where we talk stocks unfiltered.

Chris Mayer was the very first guest on The World According to Boyar back in 2018. Eight years later he's back, and he brought a new book with him. Chris runs Woodlock House Family Capital, wrote 100 Baggers, one of my favorite investing books, and just published The Investor's Odyssey, which uses Homer's story of Odysseus tying himself to the mast as a way of thinking about how investors protect themselves from their own worst instincts.

This one covers a lot of ground. Chris explains why he now starts many positions at 2% and lets them earn their way to a full weighting, why he cut most financial media out of his life, and why he believes the return you get on a stock varies inversely with the thickness of the research file. We spend a good chunk of time on Constellation Software, and I asked him what he'd need to see to actually sell it. He of course gave a thoughtful answer.

Chris also talks candidly about his three years on the board of Teqnion, a Swedish public company: the gap between what the board knows and what outside investors think they know, why it gave him more respect for activists, and why he'd join the board of every company he owns if he could. And we compare notes on AI. He has a page-and-a-half prompt that does in 15 minutes what he says would take a junior analyst a couple of weeks.

After we said goodbye, the record button was still on and we kept talking stocks. With Chris's permission, that conversation is at the end of the episode. Names that come up include Pool Corp, Uber, Brown & Brown, Markel, W.R. Berkley, and Rollins.

Get Chris's new book: The Investor's Odyssey

What we cover:

• How managing outside money changed Chris after years of writing a newsletter, and why the losses hurt more
• Why you don't really understand a stock until you own it, and the case for 2% starter positions
• Tying yourself to the mast: the habits Chris uses to save himself from himself
• Sosnoff's Law, or why the best ideas tend to have the thinnest research files
• What Chris looks for in quarterly reports when the plan is to hold for ten years
• Constellation Software: how Chris thinks about a big drawdown when the numbers haven't changed
• Why negative narratives are hard to argue with, and what the late 1990s "old economy" stocks can teach us about AI
• What he actually does when a position is down 30, 40, or 50% (Chuck Akre's advice: do your yoga)
• How Chris spends his day: 80% on existing holdings, 20% on new ideas
• Expert networks, and why maybe 20% of what you hear is worth anything
• AI as a junior analyst: what it does well, and which skills will still matter for investors
• Three years on a public company board: what the outside never sees
• Taxes, holding periods, and whether Chris would invest any differently in a tax-free account
• Thoughts on Pool Corp, Uber, Brown & Brown, Markel, W.R. Berkley, and Rollins

About Chris Mayer

Chris Mayer is the portfolio manager and co-founder of Woodlock House Family Capital, a concentrated, long-term fund he launched in January 2019 after serving as chief investment officer of the Bonner family office. Before that he spent more than a decade writing the investment newsletter Capital & Crisis. He is the author of 100 Baggers: Stocks That Return 100-to-1 and How to Find Them, How Do You Know?, and his newest book, The Investor's Odyssey. Chris sits on the board of Teqnio