The only thread in Newmark’s autobiography is social isolation. “I was academically smart, emotionally stupid. I can’t read people, and I take them too literally,” he confesses. In classrooms, he says, he experienced “tiny amounts of anti-Semitism,” but quickly amends that. “Frankly, any problems related to prejudice I faced may be because I was a show-off about academic stuff, raising my hand and answering questions. Or because I’m short. Five seven.”
In high school, he fell in love with the computer, and when he got to Case Western Reserve in Cleveland, he designed his own curriculum in computer science. It was also at Case Western that in his sophomore year he had an epiphany. Looking around the room in a communications class, he realized that not everyone had a communications problem, only he did. “It had to be me. I had difficulty communicating with most people.”
Cut to Detroit, and Boca Raton, and seventeen years in the IBM hinterlands as a systems engineer. Newmark was “mistreated by managers,” says Anthony Batt, a friend. Newmark demurs. “Some of them were trying to help me, and I didn’t get it. Occasionally, I was probably a bit of an asshole. I had difficulties dealing with people.”
Everything changed in 1993. He moved to San Francisco to work for Schwab, and the city’s spirit of personal experimentation and techie progressivism made him feel home at last. He joined the Well, the pilgrim colony of idealists on the Web that struggled with issues of free speech and intellectual property, led by Stewart Brand, whose koan was “Information wants to be free.” He was part of the Linux-inspired open-source movement, which looked on Microsoft as so much vinyl-siding tract housing on the Net’s sweeping landscape. And he entertained himself at events like the Anon Salon and Joe’s Digital Diner.
“I learned that storytelling is important,” he says.
Newmark is more practical than egghead, but the Well’s discussions of Internet community engaged him at his core. He saw people giving hours of time to one another without compensation, including professionals helping people in emergencies; he wanted to take part. So in 1995, he began sending out a list of techie events and opportunities to friends. Internet jobs, apartments, lectures. Just ten or twelve people at first. But the list grew. Within a few months, his list cracked the e-mail ceiling on CCs, 240, and so had to move to a listserv, and he had to give it a name.
A word about Newmark’s friends. He lacks interpersonal skills; he doesn’t connect. “He’s much more comfortable in e-mail than in person-to-person contact,” says programmer Weezy Muth. It struck me that he can barely distinguish between one human integer and another. On the evening following our first meeting, of four hours, Newmark failed to recognize me when I came up and introduced myself at a lecture to which he had directed me. “Bill, did you say?” Then in the hall, he threw himself down two seats away from me. He compensates for his clumsiness with the trick of trying to memorize first names. But these spray out like robotic data points, and the one-size-fits-all party talk that ensues paralyzes all within earshot.
But back to the hero ballad. Newmark wanted to call the listserv SF-events. “To hell with that, don’t make it fancy, just keep it Craigslist,” Batt said—it’s what everyone calls it anyway.
The list passed a million page views a month, and Newmark was using PERL-based code that converted e-mails to Web pages so that he could instantly publish friends’ ads. Microsoft Sidewalks (a now-defunct city-by-city Web network) approached him about running ads on the site. He said no. But he incorporated as a for-profit in 1999, quit his day job, and gave away a 25 percent share of ownership to a staffer, Phillip Knowlton, in the belief that Craigslist was a community trust that belonged to everyone. Besides, he says, he thought that if he owned the whole thing, he might develop a fat head and get “middle-aged crazy.”
Like its founder, the site had a straight and unpretentious look, without graphics, like an early Internet application. This may be Newmark’s genius. He expresses himself with a simple, naïve-sounding fervor: “The purpose of the Internet is to connect people to make our lives better.”
In 1999 the dot-bomb hit, and in 2000, amid the wreckage, Newmark made his most important hire, Jim Buckmaster, a shy, black-haired programmer fully a foot taller than Newmark who had been working at a dead start-up called Creditland.
Raised a Methodist in West Virginia, the son of a research chemist and a musician, Buckmaster is a deeply serious intellectual who had drifted for years in the left-wing demimonde: a “permastudent,” he says, in Ann Arbor, grazing from medical school to Latin and ancient Greek; an ascetic, sleeping on the floor of communal houses and grinding his own wheat to make bread; and a futurist, teaching himself unix programming and then building the Internet gateway for a vast social-sciences archive maintained at the University of Michigan. The coding skills were his ticket to Silicon Valley, where he commuted two and a half hours by bus each way to a job in Milpitas, reading Chomsky in pocket editions that looked like postage stamps in his big hands. Buckmaster has never owned a car. His disdain is at once phobic (“I don’t feel safe in them”) and political (“You see what the automobile imposes on everyone in society, regardless of whether they drive or not . . . If every single person on the Earth had an automobile, that would be an ecological Armageddon that the Earth would not recover from”).