“I remember I was lying on the bed, staring up at the ceiling. She came over and kissed me and said, ‘Welcome to New York, honey.’ She left almost immediately after.”
Not long after that, he moved in with a 31-year-old Polish model in Greenpoint, Brooklyn. (A friend notes that Mr. Webb “tends to use the term ‘model’ liberally.”) That lasted three months, but long enough for Mr. Webb to start playing at the McCarren Park tennis courts and compete in the Fibak Cup, hosted by the Polish American Tennis Association. (He would go on to win the cup three years in a row, demolishing local favorites and often playing half-drunk, which did not endear him to the Polish community; he was banned from further competition.)
He moved to Soho, started smoking Marlboro Reds and discovered that he did not need sleep.
“Work made me look at time differently,” he said. “Because either you work 100 hours a week and go home and sleep, or you don’t, and I didn’t. I just wasn’t sleeping. I was sleeping two hours, one hour a night.”
At the end of the week, he and his pals would add up the hours each had slept in the previous five days. It would average about eight. He found he didn’t like to hang out with bankers outside work. Instead of going out for drinks with the boys, he’d go home, smoke a jay and call up his friend, New York Post gossip reporter Neel Shah, and tag along with him to ridiculous, open-bar media parties.
“It was insane,” Mr. Shah told me. “He was out just as much as I was, but he didn’t sleep. I can’t even count the number of times it would be 4 a.m. and he would be like, ‘Shit, I’ve got to be at work in two hours.’ I think he always felt kind of pigeonholed in the banker category. When we would be out, and people would ask, he would say, ‘Oh, yeah, I work in finance,’ and then he would shuffle off.”
In the summer of 2007, at a Goldman banquet lunch, Mr. Webb was given the award for least usage of his BlackBerry. He went up onstage and accepted it as the efficiency award. And indeed Mr. Webb was efficient. After two years as an analyst, his contract was renewed—many weren’t.
For Graham Kay, 27, a comedian, the story of Mr. Webb’s efficiency award “sort of sums up to me why I like him. He’s sort of the one black sheep. He beat the system—he made a lot of money and got out.”
They met through a mutual friend, when Mr. Kay was living in Budapest and Mr. Webb swept through town on a post-college jaunt through Europe.
“When I first met him, I hated him,” said Mr. Kay. “He seemed like a U.S. college fraternity boy, Wall Street dumb-ass. The kind of kid who would only care about money, and all the things I despised.”
Mr. Webb thought Mr. Kay was a fancy boy who used too much hair product and had a bizarre way of walking in which he moved his shoulders violently back and forth, which brought to mind a shapely woman walking down Fifth Avenue. When both had settled in New York, they became friends.
Mr. Webb met a more highbrow friend while having lunch at Whole Foods a few years back, when he began rapping out with the gentleman sitting next to him, Peter Pazzaglini, a 64-year-old philosophy professor at Columbia University. They exchanged emails. Since then Mr. Webb has been slowly making his way through Mr. Pazzaglini’s syllabus. Every couple months they meet.
“I have observed him to be a person of high native intelligence, integrity, authenticity and transcendence,” Mr. Pazzaglini told me over the phone. “I’ve seen those qualities grow. He is interested in learning about the ways of knowing. And is not afraid to ask the great questions: Who am I? How do we become who we are? I have always told him, ‘Follow your heart. There’s an acorn embedded within you.’ David is on the journey of Parsifal.”
Last summer, Mr. Webb was promoted to an associate position at Goldman. This, it seems, was as far as Mr. Webb had intended to climb. Like making it to the finals against Johnny Chu. He had played lights-out.