“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.
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:
another quote:
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.
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.
He might have been lucky rather than have a good strategy, yes. Hard to tell.