New friday article

$7,225 invoice. 500 requests burned by one developer in a single day. “Is that even legal?”

That was Cursor, the fastest-growing AI startup (that’s not a foundational model company) in history, two weeks after switching their pricing model. The CEO had to publish a public apology. They offered refunds to every affected user between June 16 and July 4, 2025.

And Cursor isn’t even the worst example.

Anthropic quietly introduced weekly rate limits that throttle less than 5% of Claude subscribers. OpenAI started testing ads for free ChatGPT users this month. Replit’s gross margins swung from 36% to negative 14% in the span of months as their AI agent consumed more LLM resources than their pricing covered. Intercom charges $0.99 per AI resolution, and a single company’s bill can swing from $50 to $30,000/month depending on how good the bot gets.

Every AI company is figuring out pricing in real time.

$7,225 invoice. 500 requests burned by one developer in a single day. “Is that even legal?”

That was Cursor, the fastest-growing AI startup (that’s not a foundational model company) in history, two weeks after switching their pricing model. The CEO had to publish a public apology. They offered refunds to every affected user between June 16 and July 4, 2025.

And Cursor isn’t even the worst example.

Anthropic quietly introduced weekly rate limits that throttle less than 5% of Claude subscribers. OpenAI started testing ads for free ChatGPT users this month. Replit’s gross margins swung from 36% to negative 14% in the span of months as their AI agent consumed more LLM resources than their pricing covered. Intercom charges $0.99 per AI resolution, and a single company’s bill can swing from $50 to $30,000/month depending on how good the bot gets.

Every AI company is figuring out pricing in real time.

I spent two weeks mapping the pricing models of the top 50 AI startups by valuation with Moe Ali. We read every pricing page, tracked down actual cost numbers, and argued about how to categorize companies that use three models at once. Six distinct patterns emerged. Some of them surprised us.$7,225 invoice. 500 requests burned by one developer in a single day. “Is that even legal?”

That was Cursor, the fastest-growing AI startup (that’s not a foundational model company) in history, two weeks after switching their pricing model. The CEO had to publish a public apology. They offered refunds to every affected user between June 16 and July 4, 2025.

And Cursor isn’t even the worst example.

(ascac)

Anthropic quietly introduced weekly rate limits that throttle less than 5% of Claude subscribers. OpenAI started testing ads for free ChatGPT users this month. Replit’s gross margins swung from 36% to negative 14% in the span of months as their AI agent consumed more LLM resources than their pricing covered. Intercom charges $0.99 per AI resolution, and a single company’s bill can swing from $50 to $30,000/month depending on how good the bot gets.

(selfc)

Every AI company is figuring out pricing in real time.

I spent two weeks mapping the pricing models of the top 50 AI startups by valuation with Moe Ali. We read every pricing page, tracked down actual cost numbers, and argued about how to categorize companies that use three models at once. Six distinct patterns emerged. Some of them surprised us.

I spent two weeks mapping the pricing models of the top 50 AI startups by valuation with Moe Ali. We read every pricing page, tracked down actual cost numbers, and argued about how to categorize companies that use three models at once. Six distinct patterns emerged. Some of them surprised us.$7,225 invoice. 500 requests burned by one developer in a single day. “Is that even legal?”

That was Cursor, the fastest-growing AI startup (that’s not a foundational model company) in history, two weeks after switching their pricing model. The CEO had to publish a public apology. They offered refunds to every affected user between June 16 and July 4, 2025.

And Cursor isn’t even the worst example.

Anthropic quietly introduced weekly rate limits that throttle less than 5% of Claude subscribers. OpenAI started testing ads for free ChatGPT users this month. Replit’s gross margins swung from 36% to negative 14% in the span of months as their AI agent consumed more LLM resources than their pricing covered. Intercom charges $0.99 per AI resolution, and a single company’s bill can swing from $50 to $30,000/month depending on how good the bot gets.

Every AI company is figuring out pricing in real time.

I spent two weeks mapping the pricing models of the top 50 AI startups by valuation with Moe Ali. We read every pricing page, tracked down actual cost numbers, and argued about how to categorize companies that use three models at once. Six distinct patterns emerged. Some of them surprised us.