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I have read and/or listened to The Black Swan and Antifragility
but not to the first book, the namesake of his web site: fooledbyrandomness.com. Taleb is an angry man, but wants you to know that he enjoys life. He is very entertaining, and not in a cheap way, but with some depth.
He likes to talk about weightlifting and becoming your own bodyguard, about an imaginary(?) friend, "Fat Tony", who literally smells sucker-ism, and is a curmudgeonish contrarian on many subjects, and is full of clever put-downs for sundry folk not all of whom (in my opinion) deserve it, but it may keep you entertained.
He has a point though, or several points, and is doing his best to craft and/or popularize some very useful words and phrases. "Black swan" is his biggest success, ubiquitous now on radio, TV, and Web. While people may not understand it as well as he'd like, it is a sort of useful stumbling block (or road bump) for commentators who tend to con us into thinking we understand things better than we really do (and thinking we have them to thank for it). To say that the market meltdown, or the Kyoto earthquake were "black swans" at least puts some restraint on the glibness with which they are made to look predictable in retrospect.
A real gem, in my opinion, is ludic fallacy, which is basically treating the real world as if it were as well behaved, and had as simple a set of rules, as a card game, where you can say "the probability of a full house" in such and such a situation is X. Real life, or subsets of it like the stock market, politics, or war, are in fact more like Calvinball, where the rules are continually being made up.
Taleb is a serious character who seems very interested in the truth of the matter, and when not writing popular books with a shoot from the hip feel, writes serious journal articles full of mathematics and words like metaprobability, and a lot of this material -- whole books worth, is available free at fooledbyrandomness.com.