In this episode, we sit down with Tad Smith, founder of Durable Money, partner at One Roundtable Partners, and former CEO of Sotheby’s and Madison Square Garden. Tad reflects on his journey from leading global companies to teaching strategy and finance at NYU Stern. We discuss his teaching methods, including the Amazon case study that captivated students, and how it applies to understanding bitcoin and MicroStrategy today. Tad shares insights on risk versus volatility, the challenges of valuing bitcoin and MicroStrategy, and the role of patterns in investment decisions. We also explore the concept of a U.S. strategic bitcoin reserve, the biggest risks to bitcoin, and why Tad believes bitcoin is reshaping capital allocation worldwide.

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TIMESTAMPS:

0:00 - Intro

1:00 - From Sotheby’s to Madison Square Garden

3:00 - Teaching at NYU Stern: Lessons from students

5:30 - The Amazon case study that wowed students

9:00 - Patterns in history: Bitcoin's historical rhymes

12:30 - MicroStrategy’s bold bitcoin bet

17:00 - Volatility vs. risk: What investors get wrong

22:00 - Why is bitcoin so volatile?

33:00 - Should the U.S. create a strategic bitcoin reserve?

48:30 - The biggest risks to bitcoin

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