Nassim Nicholas Taleb has traded options for more than 20 years, either for major investment banks or on his own as a fund manager and pit trader but he bristles at being labeled a trader.

Taleb describes himself as a philosopher who argues that traders underestimate the role of randomness, and fund managers’ successful track records might be more easily explained by luck than skill or experience.

Unlike many options traders who collect premium from selling out–of–the–money (OTM) options, Taleb focuses on buying far OTM options that have a low probability of making money but post extraordinary returns if they do.