The Twenty Minute VCAnthropic vs The Pentagon: Who Wins? | Cursor Hits $2BN in ARR | Block's 40% Headcount Reduction
Episode Details
EPISODE INFO
- Released
- March 5, 2026
- Duration
- 1h 25m
- 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. ----------------------------------------------- Timestamps: 00:00 Intro 01:16 Anthropic vs The Pentagon: Who Wins 17:01 Was Sam Altman Wrong to Take the Deal 23:29 OpenAI's $110BN Mega Round: The Breakdown 27:44 Who Has a Bigger Valuation Premium: Sam Altman or Elon Musk 34:42 Why We Got the SaaS Apocalypse Wrong? 43:09 Why Salesforce Could be the Best Buy in Public Markets 49:03 Block Lays Off 40% of Team: AI or Overhiring 01:02:45 Cursor Hits $2BN in ARR… so not Dead? 01:17:01 How to Pick Winners in AI? ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: https://x.com/harrystebbings Follow Jason Lemkin on X: https://x.com/jasonlk Follow Rory O’Driscoll on X: https://x.com/rodriscoll Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- Legal Disclaimer: The content of this podcast is for informational and entertainment purposes only and does not constitute financial or investment advice. Any discussion of stocks, public markets, or investment strategies reflects the personal opinions of the speakers and should not be relied upon when making investment decisions. Figures, valuations, and financial data referenced may be estimates or subject to error. Always consult a qualified financial adviser before making any investment decision. The views expressed are those of the individual speakers and do not represent the views of 20VC or its affiliates. ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #anthropic #openai #cursor #ai #elonmusk #saas #samaltman
SPEAKERS
Rory O’Driscoll
guestGeneral Partner at Scale Venture Partners, focused on venture investing in software and technology.
Harry Stebbings
hostFounder and host of 20VC (The Twenty Minute VC), interviewing and analyzing startups, venture, and tech.
Jason Lemkin
guestFounder of SaaStr and venture investor known for expertise in SaaS growth, metrics, and go-to-market.
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Harry Stebbings, Anthropic vs The Pentagon: Who Wins? | Cursor Hits $2BN in ARR | Block's 40% Headcount Reduction explores aI power shifts: defense contracts, mega-rounds, layoffs, coding tools collide Anthropic’s DoD contract dispute highlights the clash between AI-company safety principles and the state’s insistence on legally unconstrained defense usage.
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