December 19, 2025

TIP777: The 1999 Dot-Com Bubble w/ Clay Finck

1 hour 10 minutes

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.

BOOKS AND RESOURCES

Join the exclusive ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Mastermind Community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.

Learn how to join us in Omaha for the Berkshire meeting ⁠here⁠.

Roger Lowenstein’s book: Origins of the Crash.

Mentioned Episode TIP693: The Power Law: Unlocking Venture Capital's Secrets w/ Clay Finck.

Follow Clay on ⁠LinkedIn⁠ & ⁠X⁠.

Related ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠books⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ mentioned in the podcast.

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