[Animats]

His trading results aren't clear. When editing the Wikipedia article, we kept running into the fact that he boasts about the performance of his funds in the years they're up, but refuses to release results for the years they're down. His funds buy options that are way out of the money, which means they lose money in years nothing bad happens. In years with a big crash, they win big. It's not clear that this is a net win over time.

[fellellor]

I guess it depends on how much they lose in each good year, ie it's subjective. This kind of investing is not for someone like myself, who doesn't like spending too much time managing money in the first place but I can see how it might work for someone more involved in the process.

[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.

[nradov]

Investing returns are objective and quantifiable. That's the opposite of subjective.