[Animats]

What it depends on is whether the people selling way out of the money options are underpricing them due to underestimating the probability of unlikely events.

[nwatson]

The hit or miss nature of black swans means you can run out of money and willing investors even when expected return is in your favor.

The only way to fund the famine years is to subsidize with a regular portfolio ... but then you don't run a black swan fund any longer.