Anthropic vs The Pentagon: Who Wins | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR

20VC

Mar 5, 2026

Posted by


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:
  • Anthropic vs The Pentagon: Who Wins

  • Was Sam Altman Wrong to Take the Deal

  • OpenAI's $110BN Mega Round: The Breakdown

  • Who Has a Bigger Valuation Premium: Sam Altman or Elon Musk

  • Why We Got the SaaS Apocalypse Wrong?

  • Why Salesforce Could be the Best Buy in Public Markets

  • Block Lays Off 40% of Team: AI or Overhiring

  • Cursor Hits $2BN in ARR… so not Dead?

  • How to Pick Winners in AI?

Share this post

Link copied

SUBSCRIBE NOW TO YOUR FAVOURITE PLATFORM

SUBSCRIBE NOW TO YOUR FAVOURITE PLATFORM

SUBSCRIBE NOW TO YOUR FAVOURITE PLATFORM

SUBSCRIBE NOW TO YOUR FAVOURITE PLATFORM

© 2024 20VC. All rights reserved.

© 2024 20VC. All rights reserved.

© 2024 20VC. All rights reserved.

© 2024 20VC. All rights reserved.