The Complex Relationship Between Wealth and Motivation in Startups

AGENDA:

00:00 – $400B in AI CapEx: Rational Investment or Madness?

05:00 – Figma's IPO: Rule of 80, $1.5B in cash, 40% margins. Unreal.

08:00 – Adobe Screwed the Deal—Should They Have Just Bought Canva?

16:00 – Pay-to-Play Deals: Heroic Hail Mary or Guaranteed Write-Off?

21:30 – How Index Is Returning $3.5B on 2 Deals

24:00 – Melio’s $2.5B Exit: Insane Growth… So Why Did They Sell?!

35:00 – Massive Penthouses and the Death of Focus: AI Founders Beware

39:00 – Chime, Anthropic, Menlo & The Art of Selling LPs the Future

41:00 – Couchbase Acquired: PE Buyers Are Back… Or Are They?

44:00 – Why No One’s Buying These 9-Figure SaaS Zombies

48:00 – If You Didn’t Grow from AI By June 30, You’re Already Dead

53:00 – Superhuman vs The AI-Natives: Who Wins the Replatforming War?

54:30 – Oracle's $30B AI Deal: Larry Did It Before You Even Started

56:00 – Scale Is Dead. Long Live Surge. The AI Data War Gets Bloody.

01:01:00 – Asana CEO Move & the Great Founder Exodus of 2025

01:06:00 – Will Cluely’s Founder Be a Billionaire by 2029? Place Your Bets