The Investor's Journey: Philosophy and Strategy

This chapter explores the early life and experiences of a notable investor, tracing their fascination with the stock market to their father's influence. It highlights their development of a unique investment philosophy that emphasizes intrinsic value and future cash flows, particularly in the tech sector, while contrasting classical value investing approaches.

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In today’s episode, Shawn O’Malley (@Shawn_OMalley_) breaks down the life and career of the great Bill Miller, the only investor to ever beat the market for 15 consecutive years.

You’ll learn how Miller invested in his first stock, Miller’s investment approach and how it differs from classical value investors, what Miller recognized as an early investor in Amazon, why he’s bullish on Bitcoin, how Miller bounced back from the 2008 Financial Crisis, how philosophy shaped his performance as an investor, plus so much more!

IN THIS EPISODE, YOU’LL LEARN

00:00 - Intro

00:08 - How Miller got his start as an investor

03:27 - How philosophy shaped Miller’s investment approach

05:26 - What is different about how Miller thinks about value investing

08:52 - What Miller recognized about Amazon before Wall Street

10:07 - Why most investors don’t have enough factor diversification

11:22 - What Miller learned from Peter Lynch

17:36 - How the cost of capital impacts companies’ ability to create shareholder value

20:57 - What went wrong for Miller during the Financial Crisis

24:09 - Why Miller decided to go solo and leave Legg Mason

31:02 - Why Miller and his son are bullish on Bitcoin

35:07 - Why Miller is usually worried about nothing in markets

*Disclaimer: Slight timestamp discrepancies may occur due to podcast platform differences.

BOOKS AND RESOURCES

Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Kyle and the other community members.
R.J. Shook's book, The Winner’s Circle.
Peter Lynch's book, One Up On Wall Street.
William Green's book, Richer, Wiser, Happer.
Check out The Value Investor’s Case for Bitcoin.
Check out Why I’m Still Betting on Bitcoin.
Check out the books mentioned in the podcast here.
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