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.