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OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds

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

Rory O’DriscollguestHarry StebbingshostJason Lemkinguest
May 28, 20261h 27mWatch on YouTube ↗

CHAPTERS

  1. AI’s ROI obsession and a blockbuster news week setup

    The hosts frame a week packed with IPO filings, revenue milestones, and layoffs, anchored by a key tension: corporate America is unusually convinced AI will pay off. They tease how public-market narratives (S-1s) and private-market behavior (token spend, hiring/layoffs) are all downstream of the same ROI question.

  2. Nvidia’s $81.6B quarter: why the stock barely moved

    They dissect Nvidia’s huge quarter and explain why a flat stock reaction can still be bullish in today’s “beat, raise, accelerate” market. The conversation emphasizes profits, market expectations, and how hyperscaler CapEx telegraphs Nvidia’s near-term outcomes.

  3. Is $3–$4T AI infrastructure spend by 2030 real? The ROI constraint

    Jensen Huang’s multi-trillion-dollar infrastructure forecast prompts a practical debate: can the next trillions in CapEx generate economic ROI? They argue the limiting factor is less technical feasibility and more whether marginal returns justify continued escalation.

  4. Uber & Microsoft signal AI productivity gains are hard to measure

    They react to claims that AI productivity benefits aren’t yet measurable, interpreting this as an early sign of an upcoming bifurcation. Some companies will ‘token max’ and see compounding gains, while others—especially margin-protectors—become skeptical as costs rise.

  5. Anthropic’s revenue & margin surge: the bull case—and the premium-price bear case

    Anthropic’s rapid growth and improving margins lead to a discussion of inevitability of profitability at scale. They also outline the vulnerability: Claude’s premium pricing could compress if enterprise buyers tighten budgets or competitors close quality gaps.

  6. Layoffs at ClickUp & Cloudflare: ‘COVID over-hiring’ vs AI-driven restructuring

    The group rejects the simplistic narrative that layoffs are just unwinding COVID-era over-hiring, pointing to natural attrition and years of performance management opportunity. They focus instead on organizational redesign, skill shifts, and AI’s role in reallocating spend from headcount to tools and top performers.

  7. A new compensation/productivity regime: $2M revenue per employee and ‘agentic experts’

    They explore a world where AI tools amplify individual output dramatically, pushing revenue-per-employee higher and widening the gap between top performers and the mid-pack. This creates both an optimistic productivity story and a dystopian reskilling pressure story.

  8. OpenAI confidentially files S-1: why timing matters vs Anthropic

    They argue OpenAI is incentivized to go public sooner rather than later if it risks becoming the clearly weaker #2 on growth and profitability. The discussion centers on narrative advantage (“category creator”) and the danger of listing after a competitor with superior metrics.

  9. Should Anthropic respond or rush? And why foundation models may need public markets

    They debate whether Anthropic must change plans due to OpenAI’s IPO timing, concluding operational excellence gives freedom. They also argue Anthropic’s capital needs (compute scaling) differ from cash-generative Stripe-like businesses, making public-market access strategically valuable.

  10. SpaceX S-1: sum-of-parts vs the ‘Elon premium’

    They read SpaceX’s filing as a bold narrative blending rockets, Starlink, and an AI/compute business, but struggle to justify the proposed valuation with conventional DCF. The gap is attributed to an ‘Elon premium’ and an aggressive TAM story that leans heavily on AI rather than SpaceX’s historic strengths.

  11. Colossus as a ‘stroke of genius’: monetizing compute like a better CoreWeave

    They highlight SpaceX/xAI’s rapid buildout of large-scale compute and a major rental deal (framed as extremely high annualized revenue) as a clever way to monetize scarce capacity. Even so, they question whether ‘renting chips’ can rationally support multi-trillion valuations without bigger strategic breakthroughs.

  12. Data centers in space: compelling narrative glue, low-probability near-term core

    They treat space-based data centers as the story that ties together launch capability and AI infrastructure, but call it unlikely to be a major revenue driver by 2030. The thesis only works if AI demand and ROI remain massive and terrestrial buildouts can’t keep pace.

  13. Polsia (‘AI slop’) raises a big round: is this the peak or a new solo-founder playbook?

    They react skeptically to Polsia’s branding and spammy growth tactics, while acknowledging an impressive product onboarding experience and the fact it’s largely a solo founder. The main criticism is asking for payment before delivering tangible value, raising doubts about retention and real utility.

  14. Exa, OpenRouter, and the picks-and-shovels stack for agents

    They argue the most durable opportunities may sit below foundation models: search, routing/switching, and other primitives agents require. Exa is positioned as a window into a future where agents need different tooling than humans, while OpenRouter benefits from rising price sensitivity and token budget management.

  15. Ragebait but real: replacing Salesforce with vibe-coded CRM + SaaS reduction + token inelasticity

    They close by ranking provocative claims, calling “vibe-coding away Salesforce” largely unhelpful except in narrow vertical cases. They also challenge the idea of being indifferent to doubled AI prices: if ROI is that high, organizations should either spend more strategically or confront that the real bottleneck is human capacity to absorb AI output.

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