Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not

20VC

Jul 17, 2025

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Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more.

Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others.

In Today's Episode We Discuss:


- Windsurf was dead—then this deal changed everything

- The Windsurf x Google x Cognition saga explained

- The OpenAI deal collapsed—what really happened

- FTC rules forced a brutal deal structure—who lost?

- The investors’ returns: who actually made money?

- Will Google’s corp dev team get fired over this?

- Cognition’s genius $220M acquisition of Windsurf: Most brilliant Deal of the Year

- The biggest recruiting flex in Silicon Valley this year

- “Roll your own SaaS” is complete nonsense

- Lovable vs Cursor vs Replit: who wins the coding war?

- Why Lovable could be the ChatGPT of builders

- Will these vibe-coded apps become durable businesses?

- The shocking churn rates hidden inside AI SaaS

- Are these $2B valuations actually... cheap?

- Grok just destroyed GPT-4 in benchmarks—WTF?!

- Why Grok might overtake OpenAI in the next 12 months

- Meta just invested $3.5B in Ray-Bans—WTF?

- Should every S&P 500 company buy Bitcoin now?

- Will Meta kill open source? What happens to Llama 5?

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© 2024 20VC. All rights reserved.

© 2024 20VC. All rights reserved.