The Black Swan seems really good, would you say it's entertaining for non-maths nerds?
One thought I've had: If you look the wealthiest guys in the industry and the world, they are more philosophical than mathematical, like Peter Thiel or Paul Graham. An exception would be someone like James Simons (hedge fund guy).
Warren Buffett says he basically just does arithmetic, and the rest of it is critical thinking and controlling your emotions. I was pleasantly surprised to see his partner Charlie Munger talk a lot about cognitive fallacies, which are in the realm of philosophy.