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

Overview

Shownote

Highlights

Transcript

Chapters

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

We Study Billionaires - The Investor’s Podcast Network

2025/12/19
We Study Billionaires - The Investor’s Podcast Network

We Study Billionaires - The Investor’s Podcast Network

2025/12/19
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

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 his...

Highlights

This episode delves into the dynamics of the dot-com bubble, using Roger Lowenstein’s 'Origins of the Crash' as a lens to examine how misaligned incentives, financial manipulation, and speculative fervor distorted market realities in the 1990s.
06:59
Stocks obtained via compensation are less psychologically valuable than those bought personally.
26:27
AI fears are overblown; Constellation Software's prospects haven't changed despite stock decline.
27:53
Revolutionary technologies don't always bring good returns
35:06
The dot-com bubble was like Wile E. Coyote running off a cliff—investors kept going until they looked down.
1:08:52
Stocks are intangible and prone to speculation more than physical assets.

Chapters

Intro
00:00
Why stock options often misalign executives and long-term shareholders
03:33
How financial engineering was abused in the 1990s market boom
08:51
How distorted incentives fueled the dot-com bubble
12:45
Why revolutionary technologies don’t guarantee successful investments
27:51
The role Wall Street analysts and the media played in amplifying speculation
31:47
How Enron’s deception exposed systemic failures in governance and oversight
39:19
Clay’s lessons for avoiding hype-driven bubbles in the future
1:11:34

Transcript

Clay Finck: You're listening to TIP. On today's episode, we're exploring one of the most dramatic chapters in financial history, the dot-com boom and the unraveling that followed, as told through Roger Lowenstein's book, Origins of the Crash. For those who...