I read this many years ago and was wowed by it. NNT sincerely believes that he has a deep understanding of the world that few others have – a prophet whose wisdom will allow the lucky reader to ascend beyond the group-thinking apes. However, having witnessed NNT's pugnacious behaviour on various Twitter debates, I had become quite disillusioned about him. This is all to say that I started this re-read with a lot more scepticism (but hopefully more intellectual maturity).
I'll start with the negatives. The book devotes many pages to various disorganised philosophical thoughts, which seem like they are there largely to remind the reader that NNT is a true renaissance man, whose bedtime reading consists of Montaigne, Poincare, Hume. His tone reminds me of Charles Kinbote, the "protagonist" of Nabokov's Pale Fire. What irritates me most, however, is a deep hypocrisy in the book. NNT strongly criticises the narrative fallacy – the tendency for humans to create an explanative story for what is actually a random sequence of events – yet at the same time presents a lot of his thinking in the form of anecdotes. NNT recognises as much, stating "There is a contradiction; this book is a story, and I prefer to use stories and vignettes to illustrate our gullibility about stories and our preference for the dangerous compression of narratives", but the recognition of it does not mitigate its existence.
He seems to believe that this disclaimer gives him license to make many assertions about the nature of black swans. I don't doubt that black swans play a large role in history, but there is a big gap between that and conceding that most/all prediction is doomed to failure. The result of this contradiction is that what NNT says may be true – and in fact, I am inclined to agree with the importance of tail events – but as it stands, the book is as unscientific as the works he so vociferously criticises.
Just like there's a fast brain and a slow brain (Thinking, Fast and Slow), there seems to be an NNT the thinker and NNT the disparager. His thoughts on black swans are insightful and semi-original, but he unfortunately interleaves this with vehement and callous criticism towards every other field, especially the social sciences. For all of the intellectual humility that NNT pretends to have, he accuses other fields of making sweeping generalisations while himself doing the same – a veritable strawman factory.
Now if you've read my review this far, it may seem that I had a very negative experience reading the book. One of the core themes is that of "fat tails", or the 80/20 principle, in which the majority of the outcome is explained by a small fraction of the inputs. It is a deep irony that I found this book to obey the same 80/20 principle: a few lessons are so valuable that they justify slogging through what can otherwise be an annoying read (due to NNT's pretentious toxicity). Chapter 13 and the technical chapters on Prediction (14+) were excellent, but even the nontechnical ideas are immensely valuable for anyone who wants to call themselves a rationalist.