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
00:52 Anthropic Delays Its $2TN IPO
04:11 Can Frontier AI Companies Even Go Public?
07:16 OpenAI’s $278BN Burn Problem
09:38 Meta’s New AI Product Takes Aim at ChatGPT
13:12 AI Agents Are Finally Building Real Software
14:30 Amazon vs Shopify: Who Wins Agentic Commerce?
17:40 Why AI Agents Could Disrupt Systems of Record
22:12 Jev: The New AI Model That Is 100x Cheaper
24:34 Why AI Is About to Unbundle the LLM Stack
29:06 The Coming Explosion in AI Model Routing & Evals
31:17 How OpenAI and Anthropic Will Respond to Cheap Models
33:21 Are Traditional Seed Rounds Disappearing?
37:17 Are Bigger Venture Checks Actually Justified?
38:49 Is FOMO Driving Today’s Venture Market?
43:18 How Should VCs Invest at the Top of the Cycle?
44:10 Why “Quiet Compounders” Are Losing Their Market
45:15 Can Triple-Triple-Double-Double Still Win in Venture?
50:22 What Should LPs Back in Venture Today?
52:46 Why Being an LP Is Harder Than Ever
54:44 Factory at $5BN: Would We Invest?
57:37 Why Coding Is the Motherlode of AI
1:00:05 Why Enterprises Won’t Trust OpenAI With Their Code
1:01:38 Legal AI: Would We Invest in Harvey or Legora?
1:05:23 Crusoe at $30.9BN: Is AI Infrastructure Overpriced?
1:07:25 The Risk of Leveraged AI Data Center Bets
1:10:50 Keith Rabois vs Airwallex
1:15:56 Why Every Founder Needs an Army of Advocates
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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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