Navigating High-Risk Investment Strategies

This chapter explores the unconventional strategies of investors taking significant risks on early-stage companies through asymmetric bets that promise high rewards. It discusses the characteristics of potential '50 baggers' and '100 baggers', using case studies like Farfetch to illustrate market mispricing opportunities. The conversation further contrasts traditional value investing tactics with modern growth stock selection, emphasizing the critical need for valuation sensitivity in today’s fluctuating financial landscape.

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In this episode, William Green chats with Samantha McLemore, the founder of Patient Capital Management. After graduating magna cum laude from Washington & Lee University, she was hired by investing legend Bill Miller & spent 20 years working with him. They co-managed Miller Opportunity Trust, a top-performing mutual fund, for a decade until Bill recently retired & anointed her as his successor. Here, Samantha shares what she’s learned over the last two decades about how to outperform by thinking differently & developing a behavioral edge.

IN THIS EPISODE YOU’LL LEARN:

00:00 - Intro

03:09 - How Samantha McLemore & Bill Miller met while she was an undergraduate.

09:53 - How an insurance settlement from a dog bite sparked her interest in investing.

16:55 - What it was like being with Bill as the market crashed after 9/11.

24:32 - Why Samantha & Bill love to invest during times of fear, pessimism, & panic.

27:43 - Why Bill & Samantha are betting on Bitcoin despite Warren Buffett’s skepticism.

41:52 - What Samantha looks for when investing in early-stage companies.

45:48 - Why it’s rational to be a long-term bull about US stocks.

50:31 - Why it’s critical to focus on valuation, regardless of how good a company may be.

57:44 - What she’s learned from spending time with Amazon founder Jeff Bezos.

01:12:19 - How the global financial crisis almost led her to quit the investment business.

01:20:14 - What’s helped her to handle the stress of being a money manager.

01:41:22 - How Samantha invests her own money.

01:42:16 - How she manages her time as a fund manager & mother of three young kids.

01:45:54 - What Peter Lynch said about the necessity of always being “in overdrive.”

01:47:49 - Why Samantha likes to invest in companies run by women.

01:56:37 - How Fidelity’s female customers outperformed male customers by trading less.

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, and the other community members.
Samantha McLemore’s investment firm, Patient Capital Management.
Samantha McLemore’s Opportunity Trust mutual fund.
Listen to William Green’s podcast interview with Daniel Goleman & Tsoknyi Rinpoche or watch the video here.
Listen to William Green’s podcast interview with Arnold Van Den Berg or watch the video here.
Website with information about Neuro Emotional Technique (NET).
“Thoughts of a Philosophical Fighter Pilot” by Jim Stockdale.
“The Mindful Self-Compassion Workbook” by Kristin Neff & Christopher Germer.
William Green’s book, “Richer, Wiser, Happier” – read the reviews of this book.

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