> IMHO his best book is his first mass market one: "Fooled by Randomness". It contains all the big ideas of his subsequent books and is an east, entertaining read.
Let me second this suggestion. "Fooled by Randomness" is great and I enjoyed it a lot. I've read it multiple times. I read the "The Black Swan" once and thought it was good. I did not finish "Antifragile".
Not really. I think he's starting to converge on "skin in the game" as a unifying thread for much of the other work. I could be wrong, but having read FBR and TBS, I don't recall seeing it put this simply ("skin in the game") until at least Antifragile, if not later. I view it as more of a progression.
Also, the style of the books is quite different. FBR is closer to a personal essay, whereas TBS is more of a mainstream nonfiction book, and Antifragile is the most philosophical/abstract.
IMHO his best book is his first mass market one: "Fooled by Randomness". It contains all the big ideas of his subsequent books and is an easy, entertaining read.