Benchmark vs a16z: Why Stage Specific Firms Win

20VC

May 8, 2025

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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.

Today’s Topics:

04:44 Analysis of $3 Billion Windsurf Acquisition

12:39 Will Mega Funds Win the Future of Venture Capital

18:39 Does Every Fund Have to do Pre-Seed to Win Series A and B Today

27:53 Why AI Will Create Massive Unemployment

31:06 The $100,000 Bet on the Future of Work 

35:52 Why Venture Has Become a Bundled Good

37:52 Why Stage Specific Firms Will Win: a16z vs Benchmark

40:16 What Does Harvard Losing It’s For Profit Status Mean for Venture

42:57 Why AI is Maiming and Not Killing Growth Companies on the Path to IPO

45:41 Decagon Raises 100x ARR: The Breakdown

52:50 Why VCs Are Upside Junkies and What That Means Today

01:03:37 Olo Looking to Sell: What Happens When Public Companies Want to Sell

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