I thought the real take away was that we (humans) have an inherently bad understanding of the true nature of randomness. He suggests that a 'Black Swan' is still a 'Black Swan' (completely new, and totally unpredictable), but there are also classes of events that we 'think' we can ascribe a probability to them, and others where we actually can.

The problem is in conflating the two.

His investment strategy, as I understand it, is to capitalize on that confusion. Which is exceptionally hard work, in spite of a summary of Taleb's idea.