It's essentially the culmination of Fooled By Randomness and The Black Swan.
I read the first book. The arrogance was a bit much, especially in a book where he's talking about the importance of randomness. But, like you, I did go off an explore about a lot of what he said. So it's a fun exercise.
There are a few great books which are too repetitive. "Black Swan" is one; he could have got all of that into a book a quarter the size and not lost much important. Another one is "Reckoning with Risk" by Gerd Giggerenzer - he takes many chapters to say people don't understand percentages, and you should really use "X people out of 10,000" when explaining risk to people.
It's kind of grating, but works for an audiobook in the car, where I might lose a few seconds due to temporary attention increase on the road. He'll reliably spend 3-4 minutes saying the same thing with minor variations when 20 seconds would do.