Taleb is an asshole. He would not be fun at parties, pointing out every single logic flaw one can possibly possess. Overlooking the lies and pride that make up so much social lubricant in specialized societies, such as quantitative analysis, is not something this guy is going to deal with. Say something stupid, he's not going to just smile and nod and be one of the boys. Seriously. But he's the type of asshole one wants around when dealing with the increasing prevalence of mathematical models used in structured finance.
Taleb hates the Gaussian.
Taleb likes the Fractal.