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 Sourcery: https://x.com/sourceryvc Brought to you by: • Brex—The modern finance platform, combining the world’s smartest corporate card with integrated expense management, banking, bill pay, & travel. As a Sourcery Listener you get: 75,000 points after spending $3,000 on Brex card(s), white-glove onboarding, $5,000 in AWS credits, $2,500 in OpenAI credits, & access to $180k+ in SaaS discounts. On top of $500 toward Brex travel, $300 in cashback, plus exclusive perks (like billboards..) visit → https://brex.com/sourcery • Turing—Turing delivers top-tier talent, data, and tools to help AI labs improve model performance—and enables enterprises to turn those models into powerful, production-ready systems. Visit: https://turing.com/sourcery • Carta—Carta connects founders, investors, and limited partners through software purpose-built for private capital. Trusted by 65,000+ companies in 160+ countries, Carta’s platform of software & services lays the groundwork so you can build, invest, and scale with confidence. Visit: https://carta.com/sourcery • Kalshi—The largest prediction market and the only legal platform in the US where people can trade directly on the outcomes of future events: https://kalshi.com/sourcery Follow Sourcery for the latest updates! https://www.sourcery.vc/ 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 (17:08) Why every software company is now an AI company (18:47) AI’s biggest bottleneck: energy & geopolitics (22:10) Policy, crypto regulation, and AI’s political risks (26:14) Lessons from the 1999 IPO boom & what it means for AI (34:29) What it takes to build a trillion-dollar company
