Investing by the Books #81 Andrew Hollingworth on 1929
The UK-based portfolio manager Andrew Hollingworth, founder of HollAnd Advisors, joins Eddie to discuss the book '1929' by Andrew Ross Sorkin. The conversation covers parallels to the 2008 financial crisis, how Andrew deals with market distress, and a couple of strong reading recommendations.
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Our conversation with Andrew Hollingworth was recorded on 13 January 2026.
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Episode Chapters
(00:00) Intro by Eddie
(00:47) Welcoming Andrew
(01:09) Andrew’s path to professional investing
(02:04) Introducing the book ‘1929’
(03:42) The author – who is Andrew Ross Sorkin?
(04:44) What differentiates this book from others about the crash
(05:51) Surprises in the book
(07:14) Why the extreme greed, why then
(09:58) Character 1: The big banker – Charles “Sunshine Charlie” Mitchell
(11:44) Character 2: Stock astrologist Evangeline Adams
(12:53) The lack of financial institutions
(14:04) Churchill’s optimism
(15:32) Parallels to 2008 and banking regulations
(16:31) Trust
(17:58) Anything that could’ve made the book better?
(18:29) Andrew’s firm HollAnd Advisors
(19:18) Andrew’s investment philosophy
(20:45) Evaluating businesses and people
(22:22) Portfolio concentration
(23:29) Ideal holding period
(25:02) Trimming
(26:02) Dealing with market distress
(27:52) Managing cash
(28:53) The risk of withdrawals
(30:18) Ambitions for the next 5-10 years
(31:44) Andrew’s reading suggestions
(34:10) Writing ambitions
(35:54) Concluding remarks
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Books Mentioned
- 1929 - Andrew Ross Sorkin
- Too Big Too Fail - Andrew Ross Sorkin
- 7 Powers – Hamilton Helmer
- Zero to One - Peter Thiel
- The Outsiders - William Thorndike
- Titan: The Life of John D. Rockefeller, Sr. – Ron Chernow
- Still Life – Sarah Winman
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Companies Mentioned
- Wise
- Meta
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More on Andrew Hollingworth
- LinkedIn: https://uk.linkedin.com/in/andrew-hollingworth-035781129
- HollAnd Advisors: https://hollandadvisors.co.uk/
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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