For context, "worse is better" refers to Gabriel's observation that products with simple implementations and complicated interfaces tend to achieve adoption faster than products with complex implementations and elegant interfaces.
One of the original motivating examples were Unix-like systems (simple implementation, few correctness guarantees in interfaces) vs. Lisp-based systems (often well specified interfaces, but with complicated implementations as the cost.)
This is amazing, almost amazing as the website of the man who wrote it: https://www.songworm.com/index.html - "I wrote the generator for these pages in Macintosh Common Lisp."
> One day in Spring 1989, I was sitting out on the Lucid porch with some of the hackers, and someone asked me why I thought people believed C and Unix were better than Lisp. I jokingly answered, "because, well, worse is better." We laughed over it for a while as I tried to make up an argument for why something clearly lousy could be good.
> JWZ excerpted the worse-is-better sections [from Lisp: Good News, Bad News, How to Win Big] and sent them to his friends at CMU, who sent them to their friends at Bell Labs, who sent them to their friends everywhere.
One of the original motivating examples were Unix-like systems (simple implementation, few correctness guarantees in interfaces) vs. Lisp-based systems (often well specified interfaces, but with complicated implementations as the cost.)