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A Guy Named Craig

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Buckmaster would never have invented Craigslist. But—picture Henry Ford redesigned by Ralph Nader—it was he who took the simple machine Newmark had invented and put it on the road for everyone.

The site was limited to San Francisco. Buckmaster launched it in Boston in June 2000 and two months later in New York, Chicago, L.A., Seattle, and Washington, D.C. Then on to 34 countries. When he came on, every posting had to be manually reviewed and approved by a staffer. Buckmaster implemented a self-posting system, in which a user sends himself an e-mail and approves the listing, whereupon it is published. He expanded the categories to include child care, political and legal discussion forums, the Missed Connections list, and, in the interest of plainness, the heading Men Seeking Sex. That could not stand. After a week, Newmark, a devotee of Sex and the City, came up with the title Casual Encounters. And Buckmaster wrote the error-message haikus that zap a user who, say, tries to resubmit the same posting in a discussion forum:

a wafer thin mint
that’s been sent before it seems
one is enough, thanks

He also set up a flagging system so that offensive posts would automatically be removed through a type of group consensus—again, users proceeding without adult supervision.

“We try to get out of the way and make changes in the site to let people better accomplish what they seem to want to accomplish,” Buckmaster says—the list’s democratic mantra.

After only eleven months on the job, Newmark made Buckmaster his president and CEO. Where Newmark is goofy and chatty, Buckmaster is shrewd and courtly. He reads the Wall Street Journal and Fortune, and appears, unruffled if unshaven, in jeans and a zip-up sweater from which his bony wrists jut like sticks, at the front door of the dilapidated Victorian house that Craigslist occupies, to answer the three camera crews that show up after it’s reported that the list is featuring ads for dangerous pit bulls by explaining the site’s policy against selling animals (a policy sometimes abrogated, by, among others, my sister).

“CEO. That’s never a title I expected to have,” Buckmaster, 43, says with a slightly perplexed look. “My father’s proud. He has drawn attention to the fact that for so long I was a sandal-wearing, bike-riding, Chomsky-reading, tofu-making hippie, and here I am a CEO. There’s not really a comeback.”

“If you try to run something similar to us and subtract the sincere mission and philosophy or, worse, try to fake it, I’m sure that’s not going to work,” says Buckmaster.

The towering and intimidating CEO is Mr. Inside, while the soft and fuzzy bite-size founder is the icon. Newmark works customer service full-time (my impression is that’s fragmented time, in between feeding Bob the cat; cooing at babies in cafés; meeting Nick Lampson, a Democrat who wants to run against Tom DeLay; and going to dinners of Stewart Brand’s Long Now Foundation) and does the green room, perfecting an interview shtick that has roots in Poor Richard’s Almanack.

“The only times I’ve been in a limo I don’t want to be . . . ”

“I don’t believe in logic. I believe in reasoning and common sense. Logic is often misleading because logic is not human or humane.”

“My problem is that in the last decade, against my wishes, I have acquired a little bit of taste.”

“If you look at the example of my fellow nerds, once you have a comfortable living, then it’s more satisfying to change the world than to make money . . . Also, we nerds tend to be less interested in fancy cars or weird comb-forward hair.”

Buckmaster and Newmark sometimes differ. Newmark was uncomfortable about having a purple peace sign as the Craigslist favicon, Buckmaster went ahead and wrote the code, and now Newmark is okay with it. Their passion is essentially the same.

Buckmaster’s face wrenches in suppressed feeling when he states that there were 40 workstations set up at the Superdome in New Orleans for 20,000 people. Working thousands of miles away, Craigslist sought to shorten the lines in the Astrodome by changing its listing format, so that its page of 100 listings by headline would appear as 100 digested listings, including contact info, so that printouts could be passed around and dozens of offers considered at once. When the Red Cross balked at handling offers of help on Craigslist, on liability grounds, Buckmaster didn’t even bother to call the agency.

“We saw the comments in the press, and it caused me in my mind to group the Red Cross with fema as a backward bureaucracy that is getting long in the tooth and possibly not up to the problem at hand,” he says. “It’s a very naïve reaction, and a five- or ten-year-old fear: We can’t trust something off the Internet.”


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