Given the recent burst of activity around enterprise pricing and contracts, I think April 2026 was the month when both OpenAI and Anthropic found product-market fit simonwillison.net/2026/May/27/...
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Simon Willison
Independent AI researcher, creator of Datasette and LLM
Independent AI researcher, creator of datasette.io and llm.datasette.io, building open source tools for data journalism, writing about a lot of stuff at https://simonwillison.net/
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Articles & links
Supposedly Anthropic are set to have their first profitable quarter. WSJ this time: www.wsj.com/tech/ai/mind...
AI Weekly's analysis
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- Anthropic projects $10.9B in Q2 2026 revenue, more than doubling Q1's $4.8B in a single quarter.
- Claude Code surpassed $1B in annualized revenue within six months of its launch, driven by enterprise developers.
- An expected $559M operating profit marks the first quarter Anthropic covers costs without relying solely on outside capital.
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When I woke up this morning I didn't think I'd be spending a bunch of time today getting familiar with Catholic theology, but here we are. Notes on Pope Leo XIV's encyclical on AI. simonwillison.net/2026/May/25/...
My notes on Gemini 3.5 Flash - 3x the price of Gemini 3 Flash but Google are planning to use it for many of their own products simonwillison.net/2026/May/19/...
Notes on Claude Opus 4.8, which Anthropic call "a modest but tangible improvement" - plus pelicans riding bicycles for each of the five different thinking efforts simonwillison.net/2026/May/28/...
I don't have much to say about this year's Google I/O because I prefer to write about products that have shipped, not just "coming soon" announcements - but here are some notes on Gemini Spark and Antigravity simonwillison.net/2026/May/20/...
Simon Willison reposted
Has been a while since I wrote about agentic engineering, so this time around some learnings of maintaining Pi as a junior maintainer to @mariozechner.at lucumr.pocoo.org/2026/5/24/pi...
Supposedly Anthropic are set to have their first profitable quarter. WSJ this time: www.wsj.com/tech/ai/mind...
Anthropic's self-reported run-rate revenue growth is wild - Axios Jim VandeHei said he couldn't find "any company — in any industry, in any era — that has scaled organic revenue this quickly at this level as Anthropic" when they were at $30B and now they're at $47B! simonwilli…
To prepare for my #PyConUS lightning talk this afternoon I decided to track down ALL of the names that @openclaw has used since November, using a script against its GitHub repo Warelay → CLAWDIS → CLAWDBOT → Clawdbot → Moltbot →🦞 OpenClaw simonwillison.net/2026/May/16/...