Forget The Black Swan. Once you strip away all the philosophising, I think this provides a better (or at least more concrete and less pretentious) insight into the mind of Nassim Taleb. This book discusses the trading and risk management of derivatives.
The book is refreshingly open, in that it discusses the various ways in which the markets can be manipulated to hit barriers and limit orders, saying this is fairly standard and should be accounted for. This is, I suppose, the flip side of gap risk.
His view of the world is almost a charicature of a numerate trader. The book goes on about things the author had to fight to explain to less numerate colleagues (the author does like to go on about himself, his views, and his abilities). On the other hand, the author dismisses the quant view of the world as precisely inaccurate, preferring instead a certain amount of street-smarts. However, he then goes on to make the sort of silly mathematical mistake he picks up on in others, as his intuition occasionally fails him. For example, either he or his editor has picked up the entirely wrong end of the stick on the reflection principle for barrier options.
His editor has a lot to answer for. The book is flabby where it should be terser, and terse where it should be more explicit. Some sections go into incredible detail over a very simple concept, while other passing remarks are annoyingly obscure. They could mean something straightforward, or something very subtle - it's hard to tell. There are plenty of graphs in the book, and for the most part these are a good thing. Sometimes, though, the graph is badly chosen, and in other cases, the axes are just left obscure. Frustrating.
It's also a bit of a time capsule. Written in the mid-'90s, the models are charmingly naive (local vol being viewed as fancy), the exotic options are straightforward, and he keeps recommending binomial trees as an appropriate pricing mechanism. More than a little rustic, nowadays.
The book is like a form of Wittgenstein's Ladder. It provides a framework for thinking about risk management, but by the time you start to feel comfortable with his arguments and the concepts behind them, you might well disagree with them! The volume provides a much better insight into (an earlier) Taleb than The Black Swan. It shows him up as yet another fairly bright, experienced derivatives trader with delusions of grandeur. What a shock.