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.
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.
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In Today’s Episode We Discuss:
00:00 Intro
00:53 Did Jason Just Kill Replit?
03:49 Why Claude Lies To You and Cannot Be Trusted
06:28 You Cannot Trust Agents. Period.
08:48 Why Windsurf Was Dead Without Claude
11:43 Cursor vs. Lovable: What’s the Better Bet?
12:49 Should You Still Invest in Cursor at $28B?
20:24 Would You Bet on Anthropic at $100B or OpenAI at $300B?
25:22 Inside OpenAI’s Secret Weapon: The Calvin French-Owen Memo
28:44 Perplexity Just Crushed ChatGPT and Claude
35:08 Figma’s IPO at $16B: Outrageous or Fair Game?
44:36 90% of Seed Funds Are Cooked: Is Rob Go Right?
52:40 How Often Do You Meet a Founder Who Can Return the Fund?
01:16:09 Which Seed Fund Would You Back Today?
01:20:39 Coldplay Concert: Astronomer’s Situation
01:22:55 Kalshi Quick-Fire Round
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