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
00:54 Was GPT-5 the Biggest AI Letdown Yet?
16:12 Should Perplexity Really Try to Buy Chrome for $34.5B?
27:35 The $3B N8N Deal: Genius Bet or Bubble FOMO?
39:06 Why Datadog’s Best Quarter Ever Still Tanked the Stock
45:30 Palantir’s 50% Growth at Scale – Can It Last? Is Palantir Overpriced?
01:01:33 Shopify’s Ruthless Path to 91% Revenue Growth With 30% Fewer Staff
01:14:19 Are Seed and Series A Valuations Now at Dangerous Highs?
01:20:29 Can a Single Founder Build a Unicorn?
01:28:46 Kalshi Quick-Fire Round
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