Both/And with Jay Michaelson

Both/And with Jay Michaelson

A.I.

Rapid-Onset Dinosaur Syndrome

All of a sudden, a big part of my identity seems headed for obsolescence.

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Jay Michaelson
Aug 12, 2026
∙ Paid

I first programmed a computer in 1982. I was 11 years old, and my family had just purchased a shiny new Apple II+. Not content with playing games, I immediately taught myself BASIC and created some rudimentary programs of my own. That was only the beginning: I first dialed into a BBS in 1987 (it was Star Trek themed) and built my first website in 1994. After law school, I co-founded an open source software company in 2000 that was successful enough to finance the various unprofitable (but fulfilling) experiments of my thirties: a Jewish online magazine, a queer Jewish nonprofit, a garage rock band and singer-songwriter side project, and the niche books I wrote for many years.

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