But I also like Seth Godin's books a lot, e.g. All Marketers Are Liars, Free Prize Inside, and Purple Cow.
A lot of my reading on web stuff has been vaguely in those categories though, in terms of either academic research, academic theory, digital ethnography stuff, psychology and sociology, marketing theory/praxis, plus whatever I've read on design and UX.
I would say the single book that founders in the tech industry would benefit from reading the most is probably Punished By Rewards by Alfie Kohn. I feel like every other startup puts themselves out of business by fucking up on the super basic things that book discusses. I end up having to explain it to people all the time.