The Twenty Minute VCOpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M
Episode Details
EPISODE INFO
- Released
- September 11, 2025
- Duration
- 1h 34m
- Channel
- The Twenty Minute VC
- Watch on YouTube
- ▶ Open ↗
EPISODE DESCRIPTION
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: 00:00 Intro 01:16 Elon Musk's Trillion Dollar Pay Package 04:26 Compensation Trends for Founders and CEOs 19:03 Ramp at $1B ARR, Brex at $700M - Is AI Causing All Boats To Rise? 24:34 Sierra at $100M ARR Worth $10B - Bubble or Brilliant Bet? 30:18 Kleiner Perkins Invests $100M into Anthropic at $183BN… WTF? 36:48 $10B in OpenAI Secondaries — What Happens When 1,000 New Millionaires Hit SF? 42:30 Anthropic Pays $1.5B to Authors — Fair Deal or Pure Piracy? 46:44 Why Did ASML Just Invest into Mistral at $14BN? 55:26 Atlassian Buys the Browser Company for $610M - Genius Move or Panic Buy? 01:09:25 The Next Wave of Aggressive Acquirers 01:26:32 IRL CEO Arrested for Fraud: Is More To Come? ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: / harrystebbings Follow Jason Lemkin on X: / jasonlk Follow Rory O’Driscoll on X: / rodriscoll Follow Jeff Lawson on X: / jeffiel Follow 20VC on Instagram: / 20vchq Follow 20VC on TikTok: / 20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #jefflawson #canva #ramp #anthropic #saas #openai #elonmusk #irl #sierra #twilio
SPEAKERS
Rory O’Driscoll
guestVenture capitalist and investor who analyzes private-market valuations and late-stage deal dynamics.
Jason Lemkin
guestSaaS-focused investor and operator known for commentary on startup scaling, VC behavior, and founder accountability.
Harry Stebbings
hostFounder and host of 20VC, a venture capital and tech interview podcast.
Jeff Lawson
guestEntrepreneur and Twilio co-founder/ex-CEO speaking from firsthand experience building a public SaaS company.
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Jason Lemkin, OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M explores aI boom reshapes valuations, compensation, liquidity, and ethics in venture Tesla’s proposed Musk pay package is framed as a board-sanctioned “double down” on moonshot outcomes, reflecting both upside ambition and fear of value collapse if Musk left.
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