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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 ↗

At a glance

WHAT IT’S REALLY ABOUT

AI IPO fever, ROI doubts, layoffs, and agent infrastructure bets collide

  1. 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.
  2. The group debates whether AI spend is producing measurable ROI, citing Uber’s difficulty measuring productivity gains and arguing that rising “cost-to-do-a-thing” for agentic workloads could force stricter token budgeting.
  3. Anthropic is portrayed as surging in enterprise with rapidly improving margins, but with a looming bear case: premium pricing may compress if enterprises become ROI-sensitive or competitors close the quality gap.
  4. OpenAI’s confidential S-1 filing is interpreted as a strategic necessity to IPO before being visibly outpaced on growth/profitability, while Anthropic’s leadership position gives it more timing flexibility.
  5. SpaceX’s S-1 is criticized as valuation “madness” driven by an Elon premium and conglomeration logic (launch + Starlink + xAI/compute), with skepticism about data centers in space and concerns about financial engineering.

IDEAS WORTH REMEMBERING

5 ideas

Nvidia’s “flat on great news” can signal strength, not weakness.

They argue markets already expect insane growth; not dropping after a blowout quarter suggests expectations were met and the business is now judged on marginal beats rather than raw magnitude.

The central 2026 question is whether incremental AI spend has provable ROI.

As token budgets move from “millions” to “hundreds of millions,” finance and HR scrutiny rises—especially if AI spend effectively displaces wage budgets and triggers layoffs.

Agentic systems may make AI cheaper per token but more expensive per outcome.

Even if token prices fall, agent workflows can consume far more tokens/compute for reasoning and tool use, raising the total cost-to-serve and forcing enterprises toward token governance.

Anthropic’s current lead is powerful, but pricing power is fragile if procurement gets serious.

They describe Claude as a premium product; if more buyers echo Uber’s skepticism, Anthropic may need to cut prices or accept slower share gains despite strong near-term traction.

OpenAI’s IPO push is framed as preemptive narrative control.

If OpenAI risks looking like “number two” on growth/profitability soon, going public earlier lets it sell the “category creator” story (ChatGPT mindshare) before comparative metrics harden.

WORDS WORTH SAVING

5 quotes

I can't remember except maybe for a year in the internet in the mid-'90s where corporate America was so convinced of the ROI of something as it is right now of AI, right? The sluice gates are open.

Rory O’Driscoll

I think it is the core question of the-- uh, it's going to be the question of the year.

Rory O’Driscoll

That's the dumbest thing I've ev- take I've ever seen on Twitter, is that this is over-hiring during COVID. Dumbest take.

Jason Lemkin

They've been lapped. They've been lapped, right? And it's pretty grim.

Rory O’Driscoll

It's SolarCity on steroids, and we're all here for it because we love AI, but it makes no sense.

Jason Lemkin

Nvidia profitability vs stock-price expectationsAI capex to 2030 and ROI constraintsToken economics: per-token cheaper, per-task cost risingAnthropic enterprise dominance, margin expansion, premium pricing riskOpenAI IPO timing and competitive positioning vs AnthropicSpaceX S-1, conglomeration narrative, Elon premium, compute leasing to AnthropicLayoffs (ClickUp, Cloudflare) and shifting CEO messagingAgent infrastructure: Exa (agent search) and OpenRouter (model routing)Polsia/“AI slop” controversy and paywall-before-value critiqueVibe coding vs SaaS replacement (CRM) realism

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