OpenAI & SpaceX S1 Drops | Anthropic Laps OpenAI at $44B ARR | Nvidia Prints $81.6B | Layoffs at Cloudflare & ClickUp
20VC roundtable (Harry Stebbings + Rory O'Driscoll + Jason). The single densest market-recap of the week. **OpenAI confidentially files its S1; SpaceX drops the largest IPO in history; Anthropic hits $44B ARR and laps OpenAI in revenue; Nvidia prints $81.6B revenue.** The roundtable's spine is the **bull-vs-bear case on Anthropic** and the **ROI-on-AI-spend reckoning**. Bull: Anthropic *'did as much in Q1 as all of last year'*, gross margins expanded **38% → 70%**, a **$559M operating profit projected for Q2**, Pareto-dominant on growth/profitability/scale. Bear: Claude is **2x the price of its competitor** and that premium may not hold once enterprises optimise token budgets (mix GPT-4-class + Sonnet + DeepSeek); **the Uber COO says a full year's Anthropic credits were spent in four months with gains 'not measurable'; Microsoft is reportedly moving off Anthropic because Opus is too expensive.** On Nvidia: **$50-56B profit in the quarter — 'the most profitable company on the planet'** (~$200B/yr run-rate), $81.6B revenue (+80%), $91B Q2 guide, $80B buyback; stock flat because *'the stock moves on the Delta news, not the total news'*. Jensen's **$3-4T AI-capex-by-2030** call frames the $64-trillion question: is the ROI there on the next $2T? Valuation skepticism is loud — *'100x trailing sales... SolarCity on steroids... the GeoCities deal of the AI era... I wouldn't buy a share'* — but **'the picks and shovels of the agentic revolution is just a good place to be.'** Plus: Cloudflare + ClickUp layoffs and the over-hiring-vs-AI-efficiency debate (Andreessen's 'overhiring during COVID' take called 'the dumbest take').
Key points
- **Anthropic laps OpenAI: $44B ARR, and the margin trajectory is the real story.** Rory: *'gross margins expanded from 38% to 70% and they're going to have a $559 million operating profit in Q2 projected.'* The path: negative-60% gross margin (FY24 prior) → +34% → 70%. *'High growth and improving margins meant profits were inevitable.'* **Direct continuation of [Gavin Baker's Anthropic-EBIT-positive framing in Issue 06](/issues/2026-05-24)** — now with the specific margin ramp. Asterisk: some of the profit may be a temporary SpaceX/Colossus discount, so the headline may flatter the trend.
- **The Anthropic bear case — the premium may not be defensible.** *'Claude is twice the price of its competitor.'* If even half the market decides the ROI isn't there for a premium product, Anthropic either cuts price to match or holds premium like Apple but cedes share. The degradation mechanism: *'folks will just use a combination of GPT-4, it's older, and some Sonnet and some DeepSeek because that's how I'm going to spend my budget'* — token-budget optimisation erodes pricing power. **The cleanest articulated short-thesis against the Anthropic-dominance narrative this week.**
- **The ROI reckoning is the week's master theme: experimental spend is about to meet the green eyeshades.** *'When you go from experimental to we spent $300 million on tokens... you get some lift in efficiency, but that means $200 million of OPEX you didn't expect, and you have to terminate a bunch of people — at that point HR comes in.'* The Uber COO data point: a full year's Anthropic credits spent in four months, gains *'probably there but not measurable.'* **Triangulates exactly with [the Fortune-20 $200M-tokens-minimal-results anecdote in this week's All-In](/issues/2026-05-31)** — two independent sources, same enterprise-unwind signal.
- **Nvidia is 'the most profitable company on the planet' and the market is rationally calm.** *'$50 billion plus, 56 billion of profits... if that continued all year that's $200 billion of profit a year'* vs Google's $100-120B. $81.6B revenue (+80%), $91B Q2 guide, $80B buyback. Why the stock barely moved: *'the stock moves on the Delta news, not the total news. They beat slightly, it's gone up slightly.'* Framing: *'Nvidia is 7% of all Americans' life savings — we're all AI investors whether we realise it or not.'* **Continues [the Nvidia-Q1 print from Issue 06 All-In](/issues/2026-05-24)** with the profitability lens foregrounded.
- **Jensen's $3-4T-by-2030 capex call sets up the $64-trillion question.** Quick math from the panel: $3T capex × 50% GPU × 70% Nvidia share ≈ **$1T of Nvidia revenue** (from ~$320B run-rate now). *'Extrapolating the growth rate of the last three or four years gets you there. But the question is, does that growth continue or do you hit economic — not technical — constraints? There has to be an ROI on that next $2 trillion.'* **The single highest-stakes macro question for the entire AI-infra cohort.**
- **Valuation skepticism is loud and named.** On the SpaceX/OpenAI S1s: *'100 times trailing sales, my God... it's SolarCity on steroids... it could be the GeoCities deal of the AI era... I love the S1 but it's all madness, I wouldn't buy a share.'* The constructive counter: *'the picks and shovels of the agentic revolution is just a good place to be investing.'* **A useful sentiment-gauge: even AI bulls are flinching at the IPO-cohort multiples** — pairs with [Gerstner's '$86B of supply vs $100T depth' framing in this week's CNBC hit](/issues/2026-05-31).
- **The layoffs debate: AI efficiency or COVID over-hiring? Panel says efficiency.** Cloudflare + ClickUp layoffs. Andreessen's 'this is just COVID over-hiring unwinding' take is dismissed: *'the dumbest take I've seen since our last show... this is not over-hiring, natural attrition is 15-25% a year.'* The structural read: once AI spend eats meaningful chunks of the wage bill, the layoff/ROI conversation *'becomes more quantitative — you have to prove it'* before terminating people. **Connects the AI-job-loss narrative to the same ROI-measurability gate running through All-In.**
- **Bifurcation thesis: the willingness to spend tracks ideological commitment to AI.** *'I can't remember except maybe a year in the mid-90s internet where corporate America was so convinced of the ROI of something. The sluice gates are open, the money is being authorized.'* But the next shoe: *'okay, that was fun, we spent $10 billion, what did we get?'* The world bifurcates between AI-native digital businesses (spend justified by token-vs-engineering-savings, e.g. DoorDash) and static-product incumbents (Uber) where the gains aren't measurable.
Notable quotes
Anthropic has done as much in Q1 as all of last year. Within a couple of quarters, Anthropic will be visibly and obviously ahead, profitable, growing more quickly and bigger. That's Pareto dominant on all three vectors this week.
Gross margins expanded from 38% to 70% and they're going to have a $559 million operating profit in Q2 projected. High growth and improving margins meant profits were inevitable.
Claude is twice the price of its competitor. If even half the world says the ROI isn't there for a premium product, either it has to cut its prices to match the competition or it maintains the premium like Apple but won't be able to maintain its market share.
It's not the 81 billion in revenue, it's the 50-something billion in profits, which makes it the most profitable company on the planet. If that continued all year that's $200 billion of profit a year.
There has to be an ROI on that next 2 trillion. The $64 trillion question is, does that growth continue or do you start to hit not technical, but economic constraints.
100 times trailing sales, my God. I love the S1, but I think it's all madness. I wouldn't buy a share. It's SolarCity on steroids and we're all here for it because we love AI. But it makes no sense.
When you go from experimental to we spent $300 million on tokens, you get some lift in efficiency, but that means $200 million of OPEX you didn't expect, and you have to terminate a whole bunch of people. At that point HR comes in.
Themes
- AI IPO supply wave & valuations
- Anthropic dominance vs premium-price bear case
- ROI-on-AI-spend reckoning
- Nvidia profitability & capex extrapolation
- AI layoffs & efficiency measurability
Mentioned
People
Companies
Ideas
- OpenAI S1
- SpaceX largest IPO ever
- Anthropic $44B ARR laps OpenAI
- Anthropic margin ramp 38%->70%
- Claude premium-price bear case
- ROI-on-AI-spend reckoning
- Nvidia most profitable company
- Delta-news stock framing
- $3-4T capex by 2030
- 100x sales / SolarCity / GeoCities skepticism
- picks and shovels agentic
- layoffs: AI efficiency vs COVID over-hiring
- bifurcation thesis