That's exactly my impression of "The Black Swan" and all his newer books. But "Fooled By Randomness", I think, is really good!

Wow this rings so true. I just read antifragile and while I like the ideas I can't imagine how insufferable the author is in person

Funny, that jibes with my perception of Taleb as well. He seems a bit smug, and I'm not sure if I'd like him or not if we met in person, but his books still seem valuable and worth reading. I would say that I'm better off for having read both The Black Swan and Fooled by Randomness. Still waiting to get around to reading Anti-Fragile, but it's definitely on the list.