In some ways, I find this book is poorly indexed as "Uncertainty (information theory)" or "Forecasting". More importantly, this book is an autobiography of someone who has clearly spent a lot of time being exposed to risk, and has interesting observations to make on how he handles that.
Taleb is criticized (unfairly, perhaps) for the inclusion of fictional examples and for "taking on" the establishment enshrined in many Nobel prizewinners. However, he's not interested in coming up with a sophisticated "theory of everything" and is very mixed in his emotions about whether "black swans" are a good or a bad thing. In some ways, he feels that he has his own answers as to when a black swan is a good or a bad thing, but leaves it to the reader to learn from the tales in the book and the tale of his life. The reader must then apply the knowledge, and to learn how to not be a "sucker", a person who is going to be victimized by the occurrence of black swans, and the book admits there are likely many paths to either suckerdom or success.
Whether you ultimately agree or disagree with the theories and suggestions of the book, this will be a fun book to read. His narrative style is engaging, and there are a multitude of small stories and interesting concepts and name-dropped characters for you to fill your imagination. He's more concerned about the ride than the destination, and even though he is constantly "getting there", making points as he goes and draws to a brilliant conclusion, you don't feel as though you've had to endure the ride to get there. It's not about nail-biting, hair-rasing uncertainty, but about looking at life as an adventure, where you accept big losses by making small bets, and collect as many free rides as you can in the process without feeling you have to bet the entire farm on just one big thrill. Unless you want to.
This is a careful, brilliantly humanistic book- it does not resort to moralizing nor feels the need to attack those who moralize either. Its enemy is the "ludic fallacy"- the tendency of "nerds" to mistake the simulation, the game, for the real thing, the map for the territory. It's a reminder to live life, and is endlessly upbeat despite having full awareness of the fragility and improbability of happiness.
That said, it is not devoid of philosophical sophistication. He does not reject science, mathematics: he is reminding you not to be fooled by overly precise models. If there is any weakness, it is that his mathematical models that he gives as examples sometimes seem to easily drawn, "straw men" to his argument. Nonetheless, it's not about what is right, per se, but about what works. In some ways, that it has worked for him is a black swan in and of itself, and this book is entirely humble, self-aware of that fact.
As long as you are willing to accept that, I feel this book is entirely a worthwhile read and an important addition to any library. The book is well referenced and topics are readily found, for when you forget and want to recall Sextus whats-his-name and need a quick place to look before digging for more information. As such, it is a handy nexus book for a more deep delve into the world of philosophy, without haughtily deigning itself to be an encyclopedia of philosophy. That said, few encyclopedic texts of philosophy could do better, and be more worthwhile, as an introduction to the Popperian perspective of thought... even if you tend to hate Popper, as much as I do!