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
00:53 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 billion dollar cloud play
46:44 Poolsuite builds its own data center
50:19 The rising cost of competing in AI
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