"I will always remember my encounter with the writer and cultural icon Susan Sontag, largely because it was on the same day that I met the great Benoit Mandelbrot. I took place in 2001, two months after the terrorist event, in a radio station in New York. Sontag who was being interviewed, was pricked by the idea of a fellow who “studies randomness” and came to engage me. When she discovered that I was a trader, she blurted out that she was “against the market system” and turned her back to me as I was in mid-sentence, just to humiliate me (note here that courtesy is an application of the Silver rule), while her female assistant gave me the look, as if I had been convicted of child killing. I sort of justified her behavior in order to forget the incident, imagining that she lived in some rural commune, grew her own vegetables, wrote on pencil and paper, engaged in barter transactions, that type of stuff.
No, she did not grow her own vegetables, it turned out. Two years later, I accidentally found her obituary (I waited a decade and a half before writing about the incident to avoid speaking ill of the departed). People in publishing were complaining about her rapacity; she had to squeeze her publisher, Farrar Strauss and Giroud of what would be several million dollars today for a book advance. She shared, with a girlfriend, a mansion in New York City, one that was later sold for $28 million dollars. Sontag probably felt that insulting people with money inducted her into some unimpeachable sainthood, exempting her from having skin in the game."
Regardless, if I hated market economics, I would also try and bilk my publishers for all they’re worth.
If they don't actively "live UP" to them, and in fact live against them, but have the hypocrisy/arrogance/rudeness to call out people merely for also living against them, then their behavior should be condemned.
What's odd about that?
Why does he feel the need to point out that Sontag's outraged assistant was "female?" That's odd.
Typically obituaries leave out the bits about "rapaciousness," so I am quite surprised that NNT "accidentally" found her obituary and read about the cost of her mansion in it. That seems unlikely to be true. I've reviewed the New York Times obituary of Sontag, and though it does contain claims of "unoriginality," "style over substance," and "controversy," it does not happen to contain the cost of her mansion. Perhaps N.N. Taleb accidentally read a different obituary than this one.
He claims to have waited so as to not "speak ill of the departed." But fifteen years after her death, Sontag remains dead. And there's little hope for her recovery.
NNT's account of this incident also elides whatever the buffoonish specifics of his side of the conversation might have been. Even the most precious and fragile of us aren't absolutely scandalized by merely discovering that a person makes their money from trading.
A fun aside: this commenter also leaves out NNT's later (in the linked article) glowing description of Dinesh D'Souza's trolling some college kids with a perpetually false and long discredited "us-vs-them" dichotomy.
I confess that the only work I've read from NNT (barring the linked article, a few visits to his increasingly timecube-esque website, and the occasional dip into his Twitter stream of consciousness) is "Black Swan," but when I did I was quite surprised to discover that nearly half the the book seemed to be dedicated to his dwelling on perceived past slights and settling scores with institutions and people that he thinks treated him badly.
Finally, to address the point of the linked Medium post: one is absolutely permitted to oppose an unjust system even if one is a beneficiary of it. Without dissenting voices, nothing will ever change for the better. NNT should be ashamed of himself for speaking ill of the dead. But more than that, he should be ashamed to have built the second act of his career as a "public intellectual" by policing who is allowed to have an opinion and what they are supposed to have an opinion about. Everything is connected and we all have "skin in the game."
Please enjoy the original article! I quite enjoyed it and I hope that it makes some people happy.
I was going to leave some comments about her other interesting works, but I don't this I can after reading this.
An interesting anecdote, but not something to base an entire life assessment on.
If a serial killer had discovered Relativity, written the Goldberg Variations, or created a fundamental algorithm like FFT, would they have been any less good and usable?
People with all kinds of faults, way worse than the hypocrisy/rudeness described above by Sontag have created all kinds of great things...
 Motives, on the other hand do matter, as they can influence what they say, or what they want to achieve with saying it
e.g. She predicted the iPhone:
> A novel about the future. Machines. Each man has his own machine (memory bank, codified decision maker, etc.) You "play" the machine. Instant everything 
> What if everything were the same, but no one talked.
It goes on... they're great..