December 19, 2025
TIP777: The 1999 Dot-Com Bubble w/ Clay Finck
We Study Billionaires - The Investor’s Podcast NetworkAbout this episode
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 Human Rights Foundation Unchained HardBlock Linkedin Talent Solutions Onramp Amazon Ads Alexa+ Shopify Vanta Public.com - see the full disclaimer here . Abundant Mines Horizon Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm