The Twenty Minute VCOpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds
Episode Details
EPISODE INFO
- Released
- May 28, 2026
- Duration
- 1h 27m
- 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 01:40 Nvidia Blowout Quarter: $81BN Revenues and Stock… Flat! 07:15 Uber and Microsoft Declare Productivity Gains Questionable from AI 24:01 The Layoffs Continue: ClickUp and Cloudflare 34:20 OpenAI S-1: Is it a Race? How Will it be Received? 38:38 Do Anthropic Rush Out Their IPO Also? 46:54 SpaceX S-1: "Why I Would Never Invest" 50:13 Why Colossus is a Stroke of Genius By Elon 55:27 Data Centers In Space is BS and Will Not Be Core to SpaceX 01:00:50 Polsia Raises $30M at $250M Price: Is this the Peak? 01:10:09 Exa Raises at $2.2BN to Build Search for Agents 01:19:42 Is Replacing Your CRM with Vibe Coding Always Ragebait ---------------------------------------------------------------------------------------------- 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 #nvidia #openai #spacex #s1 #ai #layoffs
SPEAKERS
Rory O’Driscoll
guestVenture capitalist and investing panelist focused on startup metrics and portfolio dynamics.
Harry Stebbings
hostFounder of The Twenty Minute VC (20VC) and podcast host covering venture and technology.
Jason Lemkin
guestSaaS investor and entrepreneur known for deep analysis of SaaS companies and venture markets.
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Harry Stebbings, OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds explores aI IPO fever, ROI doubts, layoffs, and agent infrastructure bets collide Nvidia’s quarter is framed as extraordinary profitability with muted stock reaction because markets now move on “delta” surprises, not headline growth, and because AI capex expectations are already priced in.
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