His books are definitely repetitive (and somewhat unorganized), but I find that saying the same thing a hundred times in slightly different ways helps drive hom

His books are definitely repetitive (and somewhat unorganized), but I find that saying the same thing a hundred times in slightly different ways helps drive home the message. People may "nod their head yes" when you give the one sentence descriptions, and think they understand it. But then they ACT in a different way, especially when they have "skin in the game". Taleb actually has a name for that: "domain dependence". That is, you can nod your head in agreement while reading a book, but then when confronted with the exact same situation in real life, you act as if you don't have that knowledge, or you act contrary to it. I've noticed this in programming vs. computer science. In a test or interview situation, someone might say they'll do things one way. But then their production code they do it a different way, just because that's the common way they've seen it done, in that particular situation. This can be good or bad -- sometimes the textbook way is actually better; sometimes not. You can also flip it around -- it also applies to the person asking the question. They might expect a certain answer of the interviewee, but when they have skin in the game, they do something else. ---- I also don't agree with the one sentence description of the Black Swan. I'd say the most important idea is that outliers are often ignored, but they're precisely what drives history. [1] And also that they're more likely than naive mathematics would suggest, i.e. "fat tails". To use an example that's HN friendly, every successful company is an outlier. And we always seem to be talking about the biggest outliers of them all (e.g. FAANG, none of which existed when I started using computers.) Making statements about the average new company isn't informative, because the average one fails and doesn't matter. [1] Thiel has a similar sentiment, something like "every big moment in business happens exactly once. The next Google isn't making a search engine, etc."