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
01:41 Jensen’s First Ever Tweet: The Open Weights Manifesto
04:47 Why OpenAI Signed the Letter
10:27 Jason’s Fable Agent Changed His Core Code Without Telling Him
14:51 Every Company Will Have an AI Security Breach in 24 Months
19:35 Etched Raises $300M: The Inference Chip Bet Against Nvidia
29:35 Travis Kalanick Is Back: $1.7B for Atoms
35:18 Google Accelerates Cloud to 82% But Prints Negative Free Cash Flow
39:10 Enterprise AI Budgets: 2026 Will Be the First Year of Real Clampdowns
48:45 Thoma Bravo’s $21B Fund: Is the PE SaaS Playbook Already Dead?
57:30 ServiceNow vs Salesforce: Which Legacy SaaS Actually Survives?
01:04:10 Mark Pincus Says Quit If It’s Too Hard
01:11:36 Stripe Hits Rule of 80: Why It’s Finally Worth the Premium
01:13:42 Will the OpenRouter Deal Actually Close?
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Legal Disclaimer:
The content of this podcast is for informational and entertainment purposes only and does not constitute financial or investment advice. Any discussion of stocks, public markets, or investment strategies reflects the personal opinions of the speakers and should not be relied upon when making investment decisions. Figures, valuations, and financial data referenced may be estimates or subject to error. Always consult a qualified financial adviser before making any investment decision. The views expressed are those of the individual speakers and do not represent the views of 20VC or its affiliates.
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