Taleb's strategy doesn't depend on a crash per se, but on unusual volatility in either direction. He accumulates a portfolio of puts or calls that misprice tai

Taleb's strategy doesn't depend on a crash per se, but on unusual volatility in either direction. He accumulates a portfolio of puts or calls that misprice tail risk. And yes it sometimes takes years to pay off, during which time the fund is paying management fees and options purchase prices. So it bleeds money over time, and then makes it back and more at random intervals. That's by design. In fact it's a similar model to Venture Capital in that way.