My (latest) AI Aha Moment

My (latest) AI Aha Moment

June 26, 2026

About this episode

Dave Winer shares his insights on using AI to analyze his blog writings and the simplicity of the solution he discovered.

Notes prepared by Claude.ai. Dave opened with an aha moment he'd been chasing for years. Long before ChatGPT, he wanted to load all his blog writing into a machine and have it grind through everything to produce a table of contents — the kind you'd find in the back of a book — surfacing the items with eighty references pointing at them and the recurring themes running through his timeline. He pointed to the browser wars of the 90s as an example, a period he wrote about heavily and, because his posts were read everywhere then, actually influenced. The dream was to load it all into an AI, read the index, and ask how a given idea developed over time. What struck me is that his solution turns out to be almost embarrassingly simple, and it only took four years. Because Dave writes everything in OPML — and always has, all the way back to the beginning, sitting in public in the scripting news repo on GitHub — you teach the AI to read OPML, drop everything into one file, and tell it to read the whole thing. His key insight is that you have to tell it more than once: the model doesn't actually ingest everything on the first pass, and it doesn't mind being nagged. You coerce the whole…

People in this episode

Host: Dave Winer

Topics covered

Mentioned in this episode

Organizations: Claude.ai, GitHub

Books & works: ChatGPT

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