The most vibrant presentation of sceptical empiricism since Dawkins stopped being beautiful.
Black Swan is a furious pompous attack on macroeconomics, journalism, and risk modelling via heuristics and biases; so it is an amazing introduction to modelling. But it's also an entire original worldview, applying to history, policy, science, and personal conduct. This is taken even further (too far) in Antifragile, which is more or less a work of evolutionary epistemology, or evolutionary practical ethics. There's a lot of redundancy between them; Fooled by Randomness gives you the highest signal:rant ratio.
The first three books are largely critical, hacking away at theory-blindness, model error, and the many kinds of people he sees as possessing unearned status (economists, journalists, consultants, business-book writers): this is the upswing, a chaotic attempt to give general positive advice in a world that dooms general positive advice.
Every other page has something worth hearing, for its iconoclasm, or a Latin gobbet, or catty anecdote, if not something globally and evidently true. I think he is right about 30% of the time, which is among the highest credences I have for anyone. I only think I am 35% right, for instance. But a core point is that he thinks his approach should work even given our intractable ignorance.
The core point, repeated a hundred times for various domains: In real life, many systems deteriorate without an irregular supply of stressors (non-fatal negative events), and actually benefit from them by constructively overreacting. By robbing such 'antifragile' systems of stressors, modern approaches to managing them do damage in the guise of helping out.
Taleb was my introduction to the post-classical theory of reason, but the project overlaps a bit with the LessWrong school I now favour. Underneath (i.e. in the technical appendices), his approach is very similar but with more conservative goals. I think Taleb saved me years of synthesis and conceptual invention.
His conduct on Twitter (ridiculous chest-beating, insulting anyone who disagrees with him, including great scholars like Tetlock and Thaler) is embarrassing, but does not detract from the accomplishment.
In one sentence: Extraordinarily rude man marries classical ethics to modern mathematics and cognitive science.
To be read when: young; if you have a news habit; when despairing of university economics.
Data 3 - highlights patterns in the world
& Theory 1&2&3&4&5 - a general concept or lens you can use to analyze many different things, &
Style 1 - teaches principles of thinking directly.