off topic: the word prose refers to ordinary written language, as opposed to, say, poetry, so when you describe his writing as near-prose like, i'm not sure what you're getting at, but i think you mean to say he writes fairly poetic prose.

Any guess at what the grandparent thought 'courtesan' meant?

I meant Courtier [1] I see NN Taleb as someone who _attends_ to power, but can never wield real power himself.

[1] https://en.wikipedia.org/wiki/Courtier

Courtier, implying well spoken andamusing

Prostitute. No this is not a complement in the context.

My guess is that "near-prose like" refers to writing that feels like it is being spoken as you read it. I can somewhat understand that.

I've never read any of this guy's work before. Despite the "preliminary draft" footnote, he strikes me as not a very thoughtful writer. I can forgive "Sometimes around the fifth century" but not "beggars who flouted they scorn of material possessions". Flouted material possessions? Flaunted their scorn of material possessions? Once I get the impression that someone is using words without fully understanding their meaning, it's hard for me to seriously consider what they are trying to convey. Perhaps that's a little harsh, but he is supposed to be a writer.

He made nearly a billion hedging on dozens of events, and thousands upon thousands of trades. I bet you haven't read a single page of his actual published papers, just his poplit stuff.

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.

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.

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.

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.

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