Initially, you are in awe of his near-prose like writing, and a couple hundred pages later, you realise that writing style is just about everything he has (all style, less substance). His ideas as well are usually pseudo-philosophical and I'm unsure if any of his writings would hold ground if it wasn't tied along with the fact that he made millions hedging on a black swan event (Again, which is a combination of picking your bets and sheer dumb luck).
Also, the more NN Taleb I read, the more pretentious he comes across as being.