[FlailFast]

Black Swan is still his best in my mind, but the Bed of Procrustes can be a nice entree; aphorisms were the original tweets, and can be consumed as such. Then I'd jump into Fooled By Randomness, and finally Antifragile (which is the weakest of them...truthfully I think the entire book could have been a chapter in Black Swan, but I'm glad he wrote it all down anyway).

[jessaustin]

I've read them all, and I agree completely with your judgement of them.

[rwhitman]

Really appreciate the recommendations, thanks!