This post buys into the common narrative about Xanadu, that it was a fundamentally good idea that failed due to some combination of poor execution, being too far ahead of its time, and the market not caring about quality (with this post in particular focusing mostly on the second thing).
In my view, Gwern makes a compelling counterargument: Xanadu was a fundamentally bad idea. The parts of it that weren't incorporated into the World Wide Web either solved problems no one actually had, or couldn't have constituted a stable equilibrium between users and publishers (i.e., even if it'd been magically willed into existence, it'd have quickly fallen apart). https://gwern.net/xanadu
In my view, Gwern makes a compelling counterargument: Xanadu was a fundamentally bad idea. The parts of it that weren't incorporated into the World Wide Web either solved problems no one actually had, or couldn't have constituted a stable equilibrium between users and publishers (i.e., even if it'd been magically willed into existence, it'd have quickly fallen apart). https://gwern.net/xanadu