Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued?
•February 19, 2026
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Why It Matters
The flow of billions into a tiny set of AI leaders signals a structural shift in venture and public markets, inflating valuations and leaving most software companies starved for capital; that concentration could amplify volatility and reshape which technology business models survive and scale.
Summary
Investors are pouring massive capital into a handful of AI winners: Anthropic closed a $30 billion round at about a $380 billion post-money valuation, Thrive raised a $10 billion fund, and OpenClaw’s creator joined OpenAI. Panelists say these deals reflect a broad rotation of capital out of traditional SaaS and into AI, driven by explosive revenue acceleration at a few firms and intense demand from multi-stage funds seeking any ownership. The frenzy has produced extreme valuation momentum—investors are prioritizing participation over selection—while many mid‑sized software companies are trading sharply lower as capital concentrates. Commentators warn this creates concentration and narrative-driven risk even as the AI leaders deliver unprecedented growth rates despite ongoing losses.
Original Description
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.
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Timestamps:
00:00 Intro
00:42 Anthropic's $30B Raise at $380B
05:53 Why SaaS Stocks Keep Getting Crushed
20:53 Wall Street's New Religion: AI Replaces Headcount
22:21 The Bear Case for Shopify: What Could Go Wrong?
33:13 Replit & Lovable are Proof Figma Missed Out: Figma; Buy or Sell?
50:27 Stripe Raises at $140BN: Is Stripe Wildly Overvalued or Adyen Undervalued?
56:51 OpenAI Buys OpenClaw
01:09:56 Thrive's $10B Growth Fund
01:12:46 Arif Janmohamed Leaves Lightspeed for New Firm
01:17:26 Workday's Founder Returns as CEO: Will it Work?
01:25:15 Which Founder Returns Next: HubSpot, Twilio, Gitlab?
01:28:58 Is Monday.com a Screaming Buy?
01:33:43 Jason and Harry Bet $200,000
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#20vc #harrystebbings #roryodriscoll #jasonlemkin #ai #anthropic #stripe #thrive #openai #saas #openclaw
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