I listened to Taleb speak at the Long Now and all he really said was, "The future is hard to predict." He was either underestimating the crowd and pulling his punches, or he had very little to say in the first place. Either way, I'm passing on The Black Swan.
All his point in fact is just "Instead of trying to predict future, how about let's just prepare for worst first?" So instead of computing probability of stock market index rising or falling in june 2009. The strategy is just "if all our current holdings dropped 75% in values? what is our protection against such happening". Instead of trying to bet on probablity, he just tries to hedge when black swan happens.