The Twenty Minute VCAnthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic
Episode Details
EPISODE INFO
- Released
- June 4, 2026
- Duration
- 1h 38m
- 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 01:24 Anthropic Files to Go Public 07:27 The "Billion-Dollar Position" Era: VCs Reset Their Expectations 18:15 The Trillion-Dollar Cash Grab: Google, SpaceX, and OpenAI Rush the Queue 21:37 Is the SaaS Apocalypse Over? 30:02 Cognition Raises $1 Billion at a $26 Billion Valuation 32:46 Token Budgeting Panic Hits Corporate America 01:00:36 Big Law Flex: Kirkland & Ellis Pledges $500 Million to Build In-House AI 01:12:41 Robinhood's AI Move: Automating Financial Planning vs Beating the Market 01:21:05 Apollo Warns PE Software Returns Are About to Be Disastrous 01:30:27 The 996 Work Ethic: Performative Theatre or Startup Reality? ---------------------------------------------------------------------------------------------- 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 #anthropicipo #ai #cognition #token #996
SPEAKERS
Rory O’Driscoll
guestVenture capital investor and panel guest providing market and investing commentary.
Harry Stebbings
hostFounder and host of 20VC (The Twenty Minute VC).
Jason Lemkin
guestFounder of SaaStr and investor/operator (former VP at Adobe).
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Harry Stebbings, Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic explores aI mega-IPO rush, VC bar resets, and token-spend backlash intensifies Anthropic’s move toward an IPO (alongside OpenAI) is framed as both ecosystem-validation and a psychological reset that raises expectations for founders, employees, and investors seeking trillion-dollar outcomes.
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