One thing I noticed when I was archive-binging his site was that there was a very distinct threshold (which I think occurred sometime in '09, but don't quote me on that), when the primary message Moldbug was trying to convey abruptly switched from "Silly progressives! Democracy doesn't work like you think it works" to "Democracy is the worst thing that ever happened in the history of forever". This transition was accompanied by a marked upswing in his general level of bitterness.