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
00:59 Figma’s IPO: Rule of 80, $1.5B in cash, 40% margins
02:48 Adobe Screwed the Deal: Should They Have Just Bought Canva?
14:17 Pay-to-Play Deals: Heroic Hail Mary or Guaranteed Write-Off?
19:01 How Index Is Returning $3.5B on 2 Deals
24:22 Melio’s $2.5B Exit: Insane Growth… So Why Did They Sell?!
33:08 Massive Penthouses and the Death of Focus: AI Founders Beware
40:14 Chime, Anthropic, Menlo & The Art of Selling LPs the Future
43:06 Couchbase Acquired: PE Buyers Are Back… Or Are They?
46:45 Why No One’s Buying These 9-Figure SaaS Zombies
52:02 If You Didn’t Grow from AI By June 30, You’re Already Dead
53:42 Superhuman vs The AI-Natives: Who Wins the Replatforming War?
58:52 Oracle’s $30B AI Deal: Larry Did It Before You Even Started
01:01:01 Scale Is Dead. Long Live Surge. The AI Data War Gets Bloody.
01:05:34 Asana CEO Move & the Great Founder Exodus of 2025
01:12:14 Kalshi Quick-Fire Round
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