Taleb is basically a man who, from youth, felt he was destined to become one of the greatest intellectual minds in the world, who’d revolutionize various fields. In this respect, Taleb resembles a young John Maynard Keynes.
And yet, Taleb did end up going in the right direction. He understood a simple fact - people who use historical or mathematical models to understand the present are engaging in a futile effort. As Rothbard and Mises themselves explained, history is just events that could have an endless number of plausible (but not actual) cause-and-effect relations between them. And to mathematize people is to treat them like atoms and planets.
The problem was that Taleb’s books do not bring that same sense of fascination that Rothbard’s books do. His books are for high time-preference intellectuals, mostly giving stretched out anecdotes, puzzles, or jokes on every single point and meandering on it. Unlike Rothbard’s books, they don’t stick to one single point and patiently explain it in a proper flow. Taleb is more of disjointed and amusing situations stitched together - a modern day Robert Nozick. It’s for those people who want to spend five minutes reading something while waiting for their flight.
It’s an irony that his beliefs demand that he be humble, but he is not humble, but rather a man who demands recognition as a great thinker who since his youth in Lebanon has read books on Marxism, Greek philosophy, mathematical theories, and other disparate subjects.
And all the same, Taleb’s understanding of problems of historical and mathematical analysis gave him the wrong lesson. While he should have instead understood that we can understand human problems through reasonining and verification through our own human minds - he instead took up the dreadful philosophy of SKEPTICISM.
Rothbard had once a great article on skeptics and their intellectual godfather Michel de Montaigne. Skepticism is one of the most deeply rotten philosophies ever conceived, borne of the worst, inhuman, self-denying thinking, which makes a man like Taleb so confused that he will use his book The Black Swan to talk about how Keynesians and Austrians are alike in some ways. The fact that a confused skeptic like Taleb is still smarter than most just reveals today’s poverty of thinking.
Skeptics have a dreadful habit of being right for the wrong reasons on many things, but then later ending up precisely wrong because of those precisely wrong reasons.