Personal worst drawdowns

We welcome back Chris Mayer to unpack his new book, The Investor’s Odyssey. How does it build upon the lessons of 100 Baggers? We dive into the realities of brutal stock drawdowns, the mechanics of compounders, and how Chris is leveraging AI in his investing process.

Stick around to the end for some fun detours into Homer, translations, and Christopher Nolan!

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Our conversation with Chris Mayer was recorded on 18 May 2026.

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For more info about the podcast, make sure to follow us on X: https://x.com/IB_Redeye. We love to hear your thoughts, so please rate and review us. And feel free to tell us about great authors, books, and investors. Thank you. /Eddie with team

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Episode Chapters

(00:00) Intro by Eddie

(01:30) Welcoming Chris

(01:47) When did Chris become an investor?

(05:02) Quick recap – the past 5 years

(06:19) Intro to The Investor’s Odyssey

(07:16) 100 Baggers vs The Investor’s Odyssey

(08:12) Chuck Akre’s impact on Chris

(11:10) The OG Odyssey

(12:48) On a plane to Omaha…

(15:16) Drawdowns and volatility

(17:28) Chris’ worst drawdown

(18:15) Resisting the Sirens

(20:07) Don’t check stock prices too frequently

(22:19) Focus on the business

(24:08) Pay attention to language

(25:47) What Chris likes about the Serial Acquirers model

(28:11) Lessons from Halma

(29:11) Diversification or a black box?

(31:17) Business survival

(33:02) Fund survival

(34:13) Chris’ use of AI

(35:27) The investable universe

(36:23) Idea generation

(37:29) Geographical exposure

(38:29) Position sizing and riding winners

(40:44) Chris’ investor ambitions for the next 10-20 years

(41:51) What Chris has read lately

(45:53) The best translation of the Odyssey

(47:13) Christopher Nolan’s new movie… The Odyssey

(48:11) Writing another book?

(48:36) Concluding remarks

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Books Mentioned

• The Investor’s Odyssey – Chris Mayer
• 100 Baggers – Chris Mayer
• Dear Fellow Time-Binder – Chris Mayer
• 100 to 1 in the Stock Market – Thomas Phelps
• Odyssey – Homer
• The Odyssey – Robert Fitzgerald translation
• The Odyssey – Robert Fagels translation
• The Odyssey – Emily Wilson translation
• Iliad – Homer
• Amusing Ourselves to Death – Neil Postman
• Lessons from Century Club Companies – Vicki TenHaken
• Plato: Complete Works
• Silent Investor, Silent Loser – Martin Sosnoff
• Humble on Wall Street – Martin Sosnoff
• Ludwig Wittgenstein: The Duty of Genius – Ray Monk
• The Odyssey – Daniel Mendelsohn
• An Odyssey – Daniel Mendelsohn

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Companies Mentioned

• Teqnion
• Berkshire Hathaway
• Apple
• Meta
• Halma

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Movies Mentioned

• O Brother, where art thou? (2000)
• The Odyssey (2026)

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More on Chris Mayer

X: https://x.com/chriswmayer

Woodlock House Capital website: https://www.woodlockhousefamilycapital.com/

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About the Podcast

Intro episode: https://www.redeye.se/podcast/investing-by-the-books/817383/0-intro-to-investing-by-the-books

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What is Investing by the Books?

Investing by the Books was founded by Henrik Andersson, Bo Börtemark, Mats Larsson and Michael Persson. It has published hundreds of book reviews in the past 10 years and operates on a non-profit basis.

Visit the website: http://www.investingbythebooks.com/

Follow on Twitter/X: https://twitter.com/Investbythebook

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What is Redeye?

Redeye is a research-centered boutique investment bank from Stockholm. Founded in 1999, Redeye cultivates investors through timeless knowledge, a humble attitude, and a strong focus on quality.

Visit the website: https://www.redeye.se/

Follow on Twitter/X: https://twitter.com/Redeye_

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Disclaimer

Notice that the content in this podcast is not, and shall not be construed as investment advice. This information is meant to be informative and for general purposes only. For full disclaimer, visit Redeye.se