Anthropic Raises $30BN at $380BN Valuation | Thrive Raises New $10BN Fund | OpenAI Buys OpenClaw | Stripe Raises at $140BN: Is Adyen Wildly Undervalued?

20VC

Feb 19, 2026

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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:
  • Anthropic's $30B Raise at $380B

  • Why SaaS Stocks Keep Getting Crushed

  • Wall Street's New Religion: AI Replaces Headcount

  • The Bear Case for Shopify: What Could Go Wrong?

  • Replit and Lovable are Proof Figma Missed Out: Figma; Buy or Sell?

  • Stripe Raises at $140BN: Is Stripe Wildly Overvalued or Adyen Undervalued?

  • OpenAI Buys OpenClaw

  • Thrive's $10B Growth Fund

  • Arif Janmohamed Leaves Lightspeed for New Firm

  • Workday's Founder Returns as CEO: Will it Work?

  • Which Founder Returns Next: HubSpot, Twilio, Gitlab?

  • Is Monday.com a Screaming Buy?

  • Jason and Harry Bet $200,000

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