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. ----------------------------------------------- Timestamps: 00:00 Intro 00:53 Everett Randle joins Benchmark 02:16 Ambition, career moves & the VC shuffle 04:15 Are VCs still the best paid? 06:25 Carry payouts & delayed returns 07:00 Revolut's $75B valuation explained 09:40 The TAM myth in startups 12:30 Why founders must expand their markets 17:05 Are AI Verticals overhyped? 19:55 The "Covid mistake" in AI investing 24:00 The rush to buy AI tools before the window closes 28:10 Will AI markets boom or deflate? 31:00 When to sell vs hold your startup 33:40 The truth about vertical SaaS 40:10 AI is changing the legal industry 41:34 OpenAI's bill...