There is a perfectly rational strategy whereby you lose a little bit of money every year if you think that the catastrophic tail event is more likely than other people think and so the risk is mis-priced.
One finance professor described it as a "100 year flood that happens every 7 years."
Taleb believes that this is true of markets and he may very well have a similar strategy (consistently buy out of the money puts).
We won't know till a certain amount of time has passed if this strategy is genius or the opposite.