In this episode, Clay explores the dot-com boom and bust through Roger Lowenstein’s book, Origins of the Crash. The book unpacks how distorted incentives, financial engineering, and speculative excess reshaped markets. By studying this period in market history, investors can better recognize recurring patterns in behavior, incentives, and speculation, and apply those lessons to avoid future manias.
IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:03:33 - Why stock options often misalign exe...
In this episode, Clay explores the dot-com boom and bust through Roger Lowenstein’s book, Origins of the Crash. The book unpacks how distorted incentives, financial engineering, and speculative excess reshaped markets. By studying this period in market history, investors can better recognize recurring patterns in behavior, incentives, and speculation, and apply those lessons to avoid future manias.
IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:03:33 - Why stock options often misalign executives and long-term shareholders
00:08:51 - How financial engineering was abused in the 1990s market boom
00:12:45 - How distorted incentives fueled the dot-com bubble
00:27:51 - Why revolutionary technologies don’t guarantee successful investments
00:31:47 - The role Wall Street analysts and the media played in amplifying speculation
00:39:19 - How Enron’s deception exposed systemic failures in governance and oversight
01:11:34 - Clay’s lessons for avoiding hype-driven bubbles in the future
Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.
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Roger Lowenstein’s book: Origins of the Crash.
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