First there was the initial approach, months ago. I ventured to email him and ask for an interview despite his long-held and often-expressed low opinion of journalists. (Heuristic: those who make the biggest deal out of disliking the media care about it the most.) To my surprise, Taleb agreed to it almost immediately even though he “doesn’t do interviews.” Some logistical back and forth ensued. Then a twist: he would only agree to be interviewed if he wasn’t photographed. Why? Because in photos he is “made to look sickly and weak.” As evidence, he attached two blurry screenshots of his YouTube lectures as well as a professional media photo, to illustrate the contrast. I was apparently meant to see how sickly and weak he looked in the professional photo (he didn’t). Luckily, The Spectator is famous for its cartoons, so I could assure Taleb that no devious photographers would be involved.

There was a small window of time in which Taleb was in New York and available for lunch. I barely caught him after a Covid scare. Finally we did meet, at Bahari Estiatorio, a Greek restaurant in Astoria, Queens. It was a freezing day in December. Taleb wore a black turtleneck and brown corduroy jacket. I greeted him, sat down, and pulled out my phone, telling him I would now begin recording the interview. Taleb adopted a hushed tone and told me he didn’t think the restaurant would like it. I said I’d done any number of interviews in restaurants and never had a problem. He said he would rather “break the ice” and just have lunch, then do the real interview later. So we just had lunch. Taleb is in his element at lunch. He ordered lahanodolmades, cabbage leaves filled with rice and ground beef. He let me have the last bit because he could tell that I liked them, he said. In total we had four appetizers and two entrées, but no dessert, because in his opinion they’re “crap” and he will only eat Lebanese pastries. We talked about everything from Elon Musk to Charles Murray, to the Talmud, cryptocurrency and genetic haplogroups. Afterwards I got on the subway and Taleb got back into his Tesla. We would do the real interview later.