I think he has a touch of the Jordan Peterson's about him - he does a very hard, overly self-confident, sell of his own ideas using somewhat opaque or idiosyncratic terminology, and some people are very impressed by that. Both seem readily overcome by emotions - Peterson can be weepy and sound distraught by Lefty ideology; Taleb is surely one of the angriest, and most arrogant sounding, Tweeters on the planet. (I reckon he would deny being emotional, though, and claim all of his angry sounding outbursts are purely intellectually driven.)
I pretty much have to rely on what other people explain as his positions, and here is a useful one by Arnold Kling on Taleb's recent book about "Skin in the Game". One part:
In his latest book, Skin in the Game, Nassim Taleb offers an approach to social and political philosophy that he believes will encourage socially constructive change and increased freedom. He starts with "double-negative utilitarianism," which means to minimize harm. This leads to a focus on the proper management of risk.Hmmm. "Decentralised entrepreneurs are heros" sounds a bit Randian to me. You know how much I like Randian capitalist hero-worship. [Sarc].
Taleb argues that only when people are, themselves, exposed to the adverse consequences of their choices do they take risks that are constructive for society. When they do not have "skin in the game," they take risks that are harmful and dangerous. This leads Taleb to advocate libertarianism, in which decentralized entrepreneurs are heroes, while those who impose centralized decisions are villains.
But you know what makes me most skeptical - Taleb spends a lot of time on Twitter fretting about GMO food and Monsanto (a topic on which I have some interest, as I have long thought it plain that some GMO ideas - food crops that allow for more and more herbicide to used on them - are dubious long term propositions that people ought to be skeptical of), but he seems to spend no time on climate change, which is clearly the most important global medium to long term risk of all.
As far as I can tell, Taleb is not a climate change skeptic; or at least, he has argued strongly for a precautionary approach to climate policy. But Arnold Kling is a skeptic, and I reckon he and other libertarians like Taleb because he is part of the libertarian "do nothing" club - he manages to find (more or less) politically tribal reasons to not be concerned about politicians who deny or want to do nothing about climate change. So, for such enlightened liberations who are not so crass to want to be aligned with Monckton, Singer or other loser and nutty sounding denialists, they can shrug their shoulders and say "no, of course I believe in climate change. But meh, what can you do? Now those bicycle helmet laws, anti-vaping regulation, and lower taxes - now that's what really gets me perturbed."