One of my favorite tech figures, a16z’s Steven Sinofsky, gives a history of “Clippy”, the helpful anthropomorphic office supply from Microsoft Office. As the product leader of the Office group in the 90s, he gives some interesting background to how Clippy came to be. I found most fascinating the time machine look back at what personal computing was like back then — how different it was to develop a software product in a world of boxed software.

Everyone makes fun of it today, but Clippy did presage the world of AI-powered “assistant” technology that everyone is getting familiar with today.

See also this Twitter thread. Love this stuff.