19 December 2025
TIP777: The 1999 Dot-Com Bubble w/ Clay Finck
We Study Billionaires - The Investor’s Podcast Network
About
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.
Ad-free episodes on our Premium Feed.
NEW TO THE SHOW?
Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter.
Check out our We Study Billionaires Starter Packs.
Follow our official social media accounts: X (Twitter) | LinkedIn | Instagram | Facebook | TikTok.
Browse through all our episodes (complete with transcripts) here.
Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool.
Enjoy exclusive perks from our favorite Apps and Services.
Learn how to better start, manage, and grow your business with the best business podcasts.
SPONSORS
Support our free podcast by supporting our sponsors:
Simple Mining
Linkedin Talent Solutions
Alexa+
HardBlock
Unchained
Amazon Ads
Vanta
Abundant Mines
Horizon
Public.com - see the full disclaimer here.
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
Learn more about your ad choices. Visit megaphone.fm/adchoices
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
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.
Ad-free episodes on our Premium Feed.
NEW TO THE SHOW?
Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter.
Check out our We Study Billionaires Starter Packs.
Follow our official social media accounts: X (Twitter) | LinkedIn | Instagram | Facebook | TikTok.
Browse through all our episodes (complete with transcripts) here.
Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool.
Enjoy exclusive perks from our favorite Apps and Services.
Learn how to better start, manage, and grow your business with the best business podcasts.
SPONSORS
Support our free podcast by supporting our sponsors:
Simple Mining
Linkedin Talent Solutions
Alexa+
HardBlock
Unchained
Amazon Ads
Vanta
Abundant Mines
Horizon
Public.com - see the full disclaimer here.
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
Learn more about your ad choices. Visit megaphone.fm/adchoices
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm