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Taleb's philosophy is based on the idea that the world is more unpredictable and uncertain than we think, and that we need to prepare ourselves for randomness and volatility. He is skeptical of grand theories and believes in the importance of localized, practical knowledge.

'The Black Swan' theory is Taleb's idea that events with low predictability and high impact - such as the financial crisis of 2008 - are more common and influential than we think, and that we should prepare ourselves accordingly.

'Antifragile' is Taleb's term for things that benefit from volatility and uncertainty, rather than being hurt by it. For example, a system that is antifragile can actually become stronger after a shock, rather than collapsing or getting weaker.

'Skin in the Game' argues that individuals and systems should be held accountable for the risks they take, and that we need more skin in the game to prevent moral hazard and other problems.

There is no reliable information on Taleb's net worth. He is primarily known for his intellectual work and does not publicize his financial assets.