OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M
20VC
Sep 11, 2025
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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.
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.
Jeff Lawson is the co-founder and former CEO of Twilio (TWLO), the developer-first cloud communications platform that pioneered APIs for voice, messaging, email (via SendGrid), and customer data (via Segment). Previously he was the founding CTO at StubHub, a product manager at AWS, co-founded Versity.
In Today’s Episode We Discuss:
Elon Musk's Trillion Dollar Pay Package
Compensation Trends for Founders and CEOs
Ramp at $1B ARR, Brex at $700M - Is AI Causing All Boats To Rise?
Sierra at $100M ARR Worth $10B - Bubble or Brilliant Bet?
Kleiner Perkins Invests $100M into Anthropic at $183BN… WTF?
$10B in OpenAI Secondaries — What Happens When 1,000 New Millionaires Hit SF?
Anthropic Pays $1.5B to Authors — Fair Deal or Pure Piracy?
Why Did ASML Just Invest into Mistral at $14BN?
Atlassian Buys the Browser Company for $610M - Genius Move or Panic Buy?
The Next Wave of Aggressive Acquirers
IRL CEO Arrested for Fraud: Is More To Come?
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