Lessons from the 1999 IPO Boom and AI Parallels

Elad compares the 1999–2000 internet IPO surge to today's AI wave and questions which companies will endure.

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Elad Gil, of Gil Capital and Gil & Co, aka one of Silicon Valley’s most influential investors, sits down with Molly O’Shea to unpack it all.. from the 1999 IPO boom to the AI bubble, and what it really takes to build durable companies across cycles.

Elad has backed more than 200 companies, from Stripe, Airbnb, and Coinbase to next-gen AI leaders like Perplexity, Harvey, and Decagon. Today, he runs Gil Capital, a multi-stage investment firm potentially managing “billions,” and continues to be one of the most insightful voices on technology, capital, and company-building.

Did we mention he’s a bit of an enigma?

Portfolio includes: Abridge, Airbnb, Airtable, Anduril, Applied Intuition, Braintrust, Brain Co, Brex, Character, Checkr, Coinbase, dbt Labs, Deel, Decagon, Figma, Flexport, Gitlab, Gusto, Harvey, Instacart, Mistral, Navan, Notion, Opendoor, PagerDuty, Perplexity, Pika, Pinterest, Retool, Rippling, Samsara, Saronic, Square, Stripe etc.

In this conversation, Elad reflects on:

Lessons from the 1999 IPO Boom: 2,000 internet companies went public, and only a handful remain. What does that mean for today’s AI rush?
AI Bubble? Why Elad believes technology waves are always “overhyped and underhyped” at the same time.
How to Spot the Next Amazon or Stripe in AI: What separates short-term success from long-term durability.
When Founders Should Sell: The four real reasons companies get acquired, and why sometimes it’s the smartest move.
Bottlenecks in AI: Why energy and regulation may shape where global training hubs are built.
Forever Private Companies: Stripe, SpaceX, and the new trend of companies that never go public.
Building a Trillion-Dollar Company: The markets, founder traits, and timing needed to reach that scale.

Elad Gil: https://x.com/eladgil

Molly O’Shea: ⁠https://x.com/MollySOShea⁠

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Chapters:

(00:00) Elad Gil

(02:00) Elad’s career arc: Google, Twitter, Color, angel investing

(02:30) Technology as a force for good

(03:20) Why Elad is building monuments

(09:09) From angel investing to a potentially multi-billion-dollar fund

(11:03) Inside Gil Capital’s small but focused team

(11:45) Thesis-driven vs. opportunistic investing

(12:43) Backing 200+ companies across waves

(15:15) Stripe, Airbnb, Figma, Instacart & investing across competition