This is a linkpost for http://www.thehindu.com/books/%E2%80%98Trump-makes-sense-to-a-grocery-store-owner%E2%80%99/article17109351.ece
Taleb's strategy is to absolutely make many bets with high payoff, low downside, expecting most of them to not pay out.
eg. http://www.newsmax.com/finance/StreetTalk/Nassim-Taleb-Shorting-Treasuries/2010/02/04/id/348993/ he was wrong, but as he puts it:
“You have a very small probability of making money,” he said. “But if you’re right, you’ll never see a public plane again.”
another quote:
"I did 700,000 trades in career, was "wrong" on between 650,000 and 695,000."
We can assume that he is either lucky, or well calibrated, since he has made quite a bit of money over the years betting on events with very long odds.
since he has made quite a bit of money over the years betting on events with very long odds
Citation needed.
I believe he tried to run a hedge fund for a while, basically buying volatility. He failed and, as far as I know, closed the fund down.