Scott Alexander is a smart guy, but not everything needs to match taste. For instance, he describes the writer of the book Sadly, Porn as remarkably erudite and so on. The community he belongs to has the habit of describing each other as very smart, certainly, and particularly having pretensions to Hegel but overall he's quite trustworthy. In any case, on actually reading the book I found it less interestingly smart and more like something the character Salvatore in The Name of The Rose might say.

But text is a serialization of an idea and it's entirely possible I have the wrong deserializer. So that's one thing perhaps you and I now have in common. And I suspect Scott Alexander just lacks the deserializer for Jack Kerouac.