I haven't read The Black Swan, but I read Fooled by Randomness. He has a secondary point that because most successes are just luck and yet people don't want to admit it, there are large profit opportunities to be made by betting on improbable events. That's really entrepreneurship in a nutshell - usually, if you look at the businesses that actually net billion dollar payouts while they're younger, you'll say "There's no possible way that can succeed." And that's why the founders make so much money when they do.

(Of course, 99% of the businesses where there's no possible way it can succeed don't actually succeed, and you get back to Taleb's argument again.)