OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won!

20VC

May 29, 2025

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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.

In Today's Episode We Talk About:

• Why “Fund Returners” Are a Myth in Late-Stage VC

• Builder.ai Implodes: $500M Gone & Fraud Allegations Begin

• The Dirty Truth About Late-Stage Venture Math

• The Hinge IPO: Who Won, Who Lost, and Why It’s a Game Changer

• The Chime Bombshell: Late-Stage VCs Forced to Crystallize Huge Losses

• Why YC Is Both Chanel and Walmart—and Has Officially Won

• Seed Is Easy. Series A Is Brutal. Here’s Why

• The Silent Killer: How Dilution Is Screwing VCs Without Them Realizing

• OpenAI’s $6B Jony Ive Deal: Genius or Delusion?

• Does OpenAI Win the Hardware War

• Duolingo, Klarna, and the Truth About AI Layoffs

• Only 20% of Unicorns Are Real. The Other 80%? Zombies

• Why 2021 Had an IPO Every Day — And Why That Won’t Return Soon

• Quickfire: AGI Dates, Half-Trillionaires, and Trump Tax Moves

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