craigslist story in Wired

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The story in this month’s Wired started when the magazine’s editors asked me a pointed question: how can a site that’s so good be so bad? Serving a vast community at an irresistible price (mostly free), craigslist nonetheless seemed the antithesis of what a modern web business should be. Oblivious to innovation and stuck in a 1997 mindset, craigslist was hogging the sector and holding things back. When the editors invited me in to propose my writing the story, they wanted an exposé.

Meanwhile, I had been wanting write about craigslist for years, ever since I saw founder Craig Newmark and CEO Jim Buckmaster give their now famous talk at the 2004  San Francisco Web2.0 conference.  (The full recording can be heard here.) Newmark stood on a milk crate, which put him nearly eye-to-eye with Buckmaster. They described their philosophy of branding (against it), of graphic design (against it), and, most intriguingly, of money. Money they were not against. But they were not exactly in favor of it, either. They seemed to think of money as a danger. Their extreme, almost theatrical caution in relation to cash was familiar to me. Many writers, musicians, and artists have it. But these were not writers, musicians or artists, they were two men running a classified advertising site. As craigslist grew dominant, its managers’ profession of disinterest in profit came to seem more and more anomalous. I did not assume they were hypocritical. I assumed they were interesting.

When we first discussed the story, the vehemence of the editors’ point of view caught me off guard. I use craigslist. The couch in my living room is from craigslist. I got rid of my moving boxes on craigslist. On the other hand, somebody tried to rob me once when I met them to purchase a DVD player they had listed on craigslist. I find searching the site to be absurdly laborious. I could see the points the editors were making against craigslist. Nonetheless I didn’t hate it. I didn’t know anybody who hated it. The most negative response I’d ever seen to craigslist  was a shoulder shrug and an eye roll that meant: “Hey, it’s free; what do you expect?”

But as I began to talk to people inside and outside the company, I began to understand that while the intensity of feeling against craigslist was a minority view, it was helpful to think about, because it came from a rare appreciation of the company’s power. To a user craigslist appears to be a local listings site. But behind each page of blue links is a publishing system that serves more than 45 million people each month, and produces 100 million dollars in revenue annually. More importantly, craigslist’s success has helped take down an entire sector of the publishing industry. The anger against Craigslist, an anger that I thought deserved to be expressed with some irony, was nonetheless  an honest tribute both to its significance and to the hopes and expectations it provokes.

In the end, after a couple of months of research, I told the editors I thought I was prepared to answer the question they originally asked: “Why can’t craigslist be better?” The answer exposed some normally unchallenged assumptions about what better means. In the series of posts that should go up over the next couple of weeks, I’m going to go into some of the details that didn’t make it into the magazine version of the story, details that may interest people who find themselves fascinated, as I was, with one of the most unusual businesses in the world.

[Update: I posted two follow-up pieces on Wired’s Epicenter blog: Craigslist vs. eBay, and Bad Advice for Newspapers]