Stripe exec: AI trains on words yet is terrible at writing

jeff_weinstein · x · 2026-10-27

jeffweinstein finds it curious that AI, trained on words, is so bad at writing it makes him seasick — yet handles many other complex tasks well. He sort of understands why, but says it makes him long for human writers. A takes on the gap between next-token prediction and genuine writing quality.

Related event: Ex-Stripe Designer Calls Out AI's Surprisingly Bad Writing(2 posts)→

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