20VC: Figma's IPO: The Full Breakdown | Index Returns $3.5BN on Two Deals | Why Melio's $2.5BN Acquisition is "Discouraging" | Asana's New CEO and the Great Founder Exodus | Oracle's $30BN AI Deal and What it Means for Incumbents

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