Craigslist founder Craig Newmark. *

Photo: PLATON * The Internet's great promise is to make the world's information universally accessible and useful. So how come when you arrive at the most popular dating site in the US you find a stream of anonymous come-ons intermixed with insults, ads for prostitutes, naked pictures, and obvious scams? In a design straight from the earliest days of the Web, miscellaneous posts compete for attention on page after page of blue links, undifferentiated by tags or ratings or even usernames. Millions of people apparently believe that love awaits here, but it is well hidden. Is this really the best we can do?

Odd perhaps, but no odder than what you see at the most popular job-search site: another wasteland of hypertext links, one line after another, without recommendations or networking features or even protection against duplicate postings. Subject to a highly unpredictable filtering system that produces daily outrage among people whose help-wanted ads have been removed without explanation, this site not only beats its competitors—Monster, CareerBuilder, Yahoo's HotJobs—but garners more traffic than all of them combined. Are our standards really so low?

But if you really want to see a mess, go visit the nation's greatest apartment-hunting site, the first likely choice of anybody searching for a rental or a roommate. On this site, contrary to every principle of usability and common sense, you can't easily browse pictures of the apartments for rent. Customer support? Visit the help desk if you enjoy being insulted. How much market share does this housing site have? In many cities, a huge percentage. It isn't worth trying to compare its traffic to competitors', because at this scale there are no competitors.

Each of these sites, of course, is merely one of the many sections of craigslist, which dominates the market in facilitating face-to-face transactions, whether people are connecting to buy and sell, give something away, rent an apartment, or have some sex. With more than 47 million unique users every month in the US alone—nearly a fifth of the nation's adult population—it is the most important community site going and yet the most underdeveloped. Think of any Web feature that has become popular in the past 10 years: Chances are craigslist has considered it and rejected it. If you try to build a third-party application designed to make craigslist work better, the management will almost certainly throw up technical roadblocks to shut you down.

Craigslist is not only gigantic in scale and totally resistant to business cooperation, it is also mostly free. The only things that cost money to post on the site are job ads in some cities ($25 to $75), apartment listings by brokers in New York ($10), and—in a special case born of recent legal trouble—advertisements in categories commonly used by prostitutes, because authorities encourage vendors to maintain a record that would aid investigators. There is no banner advertising. They won't let you join them, and at this price you can't beat them either.

At times it has occurred to people that the problems with craigslist could be solved by appealing to its eponym, Craig Newmark. Newmark is under lots of pressure these days. His company is being sued by eBay, a competitor and minority shareholder angry at being excluded from the company's deliberations. The attorney general of South Carolina has blustered about prosecuting his CEO for facilitating prostitution, and there have been strong challenges from law enforcement agencies in other states, too. The tabloids have relentlessly played up stories about two so-called craigslist killers, one who allegedly used the site's erotic-services section to lure victims and another who used the help-wanted ads. Newmark responds to such criticism with extreme serenity. Inquire about his finances and he talks about his hummingbird feeder. When his Twitter page asks him, "What are you doing?" he retweets in the voice of a squirrel.

"Run, run, run," he says. "Dig, dig."

Though the company is privately held and does not respond to questions about its finances, it is evident that craigslist earns stupendous amounts of cash. One recent report, from a consulting firm that counted the paid ads, estimates that revenue could top $100 million in 2009. Should craigslist ever be sold, the price likely would run into the billions. Newmark, by these lights, is a very rich man. When anybody reminds him of this, the craigslist founder says there is nothing he would care to do with that much money, should it ever come into his hands. He already has a parking space, a hummingbird feeder, a small home with a view, and a shower with strong water pressure. What else is he supposed to want? Frustration over these sorts of replies sometimes becomes comical. In a July 2007 television interview, Charlie Rose spent half the program attempting to get Newmark to admit his good fortune, and failing. "I don't have anywhere near as much control as you think," Newmark said.

"I'm not talking how much control; I'm talking percentage of ownership," Rose said. Rose is usually kind to his guests, but the scent of unacknowledged wealth brought out his ferocity.

"Oh, same thing from my point of view," Newmark said, trying to move the topic along.

"Do you own more than 50 percent of craigslist or not?" Rose asked.

"No."

"You don't?"

"Correct."

"In other words, other people own that, or you've given it away or whatever."

"Could be, Charlie."

"OK, but I'm—why are you so ...?"

"Coy?"

"Yeah."

"It doesn't matter," Newmark said. "I mean ..."

"I know it doesn't matter," Rose repeated, his face a mask of pain.

Newmark's claim of almost total disinterest in wealth dovetails with the way craigslist does business. Besides offering nearly all of its features for free, it scorns advertising, refuses investment, ignores design, and does not innovate. Ordinarily, a company that showed such complete disdain for the normal rules of business would be vulnerable to competition, but craigslist has no serious rivals. The glory of the site is its size and its price. But seen from another angle, craigslist is one of the strangest monopolies in history, where customers are locked in by fees set at zero and where the ambiance of neglect is not a way to extract more profit but the expression of a worldview.

The axioms of this worldview are easy to state. "People are good and trustworthy and generally just concerned with getting through the day," Newmark says. If most people are good and their needs are simple, all you have to do to serve them well is build a minimal infrastructure allowing them to get together and work things out for themselves. Any additional features are almost certainly superfluous and could even be damaging.

Newmark has been working hard to extend the influence of his worldview. His public pronouncements have the delighted yet apologetic tone of a man who has stumbled on a secret hiding in plain sight and who finds it embarrassingly necessary to point out something that should long have been obvious. He seems to have discovered a new way to run a business. He suspects that it may be the right way to run the world.

Public spirited and mild-mannered, politically liberal and socially awkward, Newmark has one trait that mattered a lot in craigslist's success: He is willing to perform the same task again and again. During the company's first years, Newmark approved nearly every message on the list, and in the decade since he has spent much of his time eliminating offensive ones. Even by the most conservative accounting, he has passed judgment on tens of thousands of classified ads. Very few people could do this and thrive.

Newmark knows that he is not typical. He tends to interpret things literally, and when he was younger other people often confused him. In 1972, while still a college student, he read Language in Thought and Action, the classic book on communication by S. I. Hayakawa, and it helped him understand himself better. "All of a sudden I'm thinking, 'It can't be that everyone else has a problem. It has to be me,'" he says.

We are sitting in a San Francisco coffee shop called Reverie Café Bar, where Newmark spends long hours and has given countless interviews. Many things in his life are a matter of routine. When he talks, he calls upon a repertoire of conversational gambits he has been collecting forever, and he has a selection of sound effects on his mobile phone, such as a cymbal crash, that he can trigger to make it clear he is joking. When people misunderstand him, he doesn't get upset. "I'm the Forrest Gump of the Internet," he says. He loves customer service. "I'll only be doing this as long as I live," he says. He taps his phone, triggering a ghostly whaaahahaha. "And after that, who knows?"

Email has always been an ideal outlet for Newmark's genial nature. Craigslist began in 1995 as a mailing list with announcements of events of interest to technical people, and as more of them began to subscribe, he encouraged readers to post their own news, archived the messages on a Web page, and tried to make sure all the content was legitimate. After Netscape's IPO in August of that year, craigslist became a portal into the dotcom scene. Within two years, he had thousands of readers, most of whom he didn't know. This was a big responsibility for somebody who is not an extrovert. "I used to email him every day," says Christina Murphy, one of the first tech recruiters to use craigslist regularly. "If I made a mistake in a job posting, I would have to call him and ask for a change. It drove him insane." Murphy, along with an Internet consultant named Nancy Melone, began meeting with Newmark, trying to map out a more professional future for craigslist that didn't require its founder to take phone calls. Job postings were an obvious source of revenue, and in 1998 they launched a nonprofit called List Foundation. Recruiters would pay $30 for ads, everything else would be free, and any money left after paying the cost of upkeep and administration would be given away. Melone was CEO. Newmark's willingness to cede so much control worried Murphy, who soon quit the venture. "It was a beautiful, perfect little world," she says. "And it was being taken over by other forces."

For nearly a year, the site was available at two URLs, craigslist.org and the less embarrassingly personal listfoundation.org. But Melone and Newmark were pulling in different directions, or rather, Melone was pulling and Newmark was digging in his heels. By the end of the decade, the Internet frenzy was at its peak and the smartest minds of the new industry all agreed that the right strategy was to get big fast in anticipation of a sale or an IPO. Melone wanted to raise prices. Newmark worried about charging for listings at all. Melone wanted to become a dotcom; Newmark was wedded to the idea that craigslist was a community service. Melone was gregarious, a talker. Newmark had vast powers of passive resistance. A split was inevitable, and one day in late September 1999, craigslist users who came in through the listfoundation.org address found themselves automatically bounced to a new, for-profit Web site, called MetroVox. Run by Melone, it offered similar sorts of community listings and had a far more aggressive plan to grow. Melone said that Newmark had authorized the switch; Newmark announced that he'd been blindsided.

This was craigslist's first serious competitive challenge, and perhaps its last. Newmark had some personal qualities that ought to have been fatal in an entrepreneur. Aside from his communication problems and an aversion to exerting authority, he cared nothing for entrepreneurship. But in the battle with MetroVox he had an asset that more than compensated for these shortcomings: For years he had worked on his site with an uncanny, machine-like constancy, doing all the painstaking and repetitive things that would make most people desperate with frustration and boredom, and he had done them happily. And now his users paid him back in the most obvious possible way: They stopped using the List Foundation address, resumed posting their free ads at craigslist.org, and emailed Newmark when problems occurred. Less than a year later, the bubble burst and MetroVox faded away.

Newmark abandoned the idea of running craigslist as a nonprofit, which would have required him to learn and follow too many rules. He realized that nobody could stop him from giving away his money if he made too much of it, and in the meantime he handed out a significant portion of his ownership to others as a way to avoid acquiring too much authority. "I was worried about going middle-aged crazy," he says. He also put great distance between himself and any executive responsibility. The current CEO, Jim Buckmaster, joined the site in 2000 as a programmer and handles every business and strategic issue. It was Buckmaster who crafted the current strategy for growth—a slow, bloblike, seemingly unstoppable accretion of new craigslist cities, each an exact clone of the others, launched with no marketing or publicity. Sometimes a new site grows very slowly for a long time. But eventually listings hit a certain volume, after which the site becomes so familiar and essential that it is more or less taken for granted by everybody except the distressed publishers of local newspapers. Revenue from newspaper classified ads is off nearly 50 percent in the past decade, a drop that comes to almost $10 billion. Only a fraction of this loss is because of Newmark's company, but as the largest online classified site, craigslist is easy to blame.

Because he is the founder of a remarkable Internet company that also happens to be helping the nation's dailies go out of business, Newmark's opinion is eagerly sought, and he spends an increasing amount of time at conferences and international meetings, where he attempts to answer questions about how to best defend the public interest in an era of cheap and ubiquitous media. As we watch the birds on the patio of Reverie, Newmark tries out some of the phrases he is hoping to use in the coming months as he unfolds the lessons of craigslist. "My big mission is to help make grassroots democracy as much a part of our government as representative democracy," he says.

Jim Buckmaster was hired as a programmer in 2000. A year later he became CEO.

Platon, grooming by Tamara Brown/Artist Untied Many people who have heard Newmark's public remarks find the ideals admirable but difficult to apply. What would such an approach mean in practice? His cause is not helped by the fact that if the craigslist management style resembles any political system, it is not democracy but rather a low-key popular dictatorship. Its inner workings are obscure, it publishes no account of its income or expenses, it has no obligation to respond to criticism, and all authority rests in the hands of a single man. Ask Newmark about any feature you would like to see on craigslist and you will always get the same response.

"Ask Jim," he says.

"How do you get your feedback? Have you ever done a poll or anything like that?"

"The thought makes me tired. But you can suggest that to Jim if you wish."

"What if Jim says no?"

"If you want to ask him again, you can," he says.

At this point in our conversation I begin to feel the spirit of Charlie Rose upon me. After all, Newmark is the founder, a major shareholder, and the public face of the company.

"What would it take to get you to fire Jim?" I ask.

Newmark matches me mischief for mischief.

"Ask Jim."

It is easy to find hypocrisy in the idealism of a business owner who prescribes democracy for others while relieving himself of the tiresome burden of democratic consultation in the domain where he has the most power. But of course, craigslist is not a polity; it is just an online classified advertising site, one that manages to serve some basic human needs with startling efficiency. It is difficult to overstate the scale of this accomplishment. Craigslist gets more traffic than either eBay or Amazon .com. eBay has more than 16,000 employees. Amazon has more than 20,000. Craigslist has 30. Craigslist may have little to teach us about how to make decisions, but that's not the aspect of democracy that concerns Newmark most. He cares about the details, about executing all the little obvious things we'd like government to do. "I'm not interested in politics, I'm interested in governance," he says. "Customer service is public service."

Last year Newmark got about 195,000 email messages. He estimates that roughly 60 percent were spam. He read all the rest and replied to many. He has a boss now, a customer service manager named Clint Powell, who was hired about six years ago. But he maintains his habits for reasons that have little to do with the normal logic of work. They are part of his identity, an unconventional mode of self-realization through which he took hold of a barrier that always separated him from the world and made it into a kind of performance. Athletes compete. Artists create. Newmark answers email. He knows that this will seem absurd from the outside, but he is blessed not to care. In fact, he likes to treat people to a laugh when he can. It's sometimes impossible to discern his intention exactly, and this is essential to the effect. On our way out of the cafè, I step aside to let Newmark go ahead, and he walks face-first into the plate glass door.

Jim Buckmaster is tall and thin, Newmark is short and round, and when they stand together they look like a binary number. In 2004, I saw them give a talk in which Newmark, who is 5'7", stood on a milk crate and was still barely eye-to-eye with his CEO, who is 6'7". It was a memorable performance, but they don't have much opportunity for the gag these days because their joint appearances are rare. At the craigslist office, the two men work in the same room, but their desks are set up so they sit back-to-back. They are not social friends, and in fact they almost never talk. Newmark does not excel at chitchat, and Buckmaster is a quiet type, too.

Buckmaster dropped out of medical school at the University of Michigan in 1986. He hung around the university for 10 years, studying the classics, doing data entry work, and teaching himself programming. By 1999, he was working as a webmaster in San Francisco for a dotcom called Creditland, where he was not happy. "The marketing side had attained ascendancy," he says. He posted his résumé on craigslist, and Newmark found it.

Craigslist was very unlike Creditland. "It wasn't even really clear who decided to hire me," Buckmaster says. He looked around and began finding things to do. He wrote forum software to give users a chance to interact. When he realized that every post had to be reviewed and published by hand, he created the automated process that allowed craigslist to grow. He coded a search engine. A year after he arrived he was CEO. There was no competition for the job, no ritual transfer of power, and no instructions. "In the entire time I've been here, I don't think Craig has ever said to me, 'This is the way it has to be,'" Buckmaster says. The only topic he can remember their disagreeing about is the peace sign that adorns the craigslist Web address. "Craig thought it was associated with the hippies and that hippies were discredited," Buckmaster says. "Whereas I think peace is among the most desirable things you can have."

The long-running tech-industry war between engineers and marketers has been ended at craigslist by the simple expedient of having no marketers. Only programmers, customer service reps, and accounting staff work at craigslist. There is no business development, no human resources, no sales. As a result, there are no meetings. The staff communicates by email and IM. This is a nice environment for employees of a certain temperament. "Not that we're a Shangri-La or anything," Buckmaster says, "but no technical people have ever left the company of their own accord."

The purity of this culture is its most tenaciously guarded asset. A few years ago, Phillip Knowlton, a Bay Area psychologist who was on the craigslist staff in the site's early years, sold his 28 percent stake in the company to eBay. Buckmaster and Newmark approved eBay founder Pierre Omidyar, himself a programmer, as the representative of eBay on the craigslist board. But at that point, Omidyar no longer ran eBay, and he was replaced by an eBay vice president who had overseen the acquisition of a craigslist competitor in Europe. When eBay launched a competing service in the US, Buckmaster responded by reorganizing craigslist and weakening eBay's influence. The companies have since sued each other. While the dueling complaints hinge on questions of stock dilution and conflict of interest, it is hard to imagine any conventional business executive being satisfied with the way craigslist operates. What kind of company declares itself uninterested in maximizing profit? "Companies looking to maximize revenue need to throw as many revenue-generating opportunities at users as they will tolerate," Buckmaster says. "We have absolutely no interest in doing that, which I think has been instrumental to the success of craigslist."

Buckmaster and I talk in the San Francisco penthouse condo of Susan MacTavish Best, who owns a small PR company. Best and Buckmaster lived together as a couple for five years. Though they are now separated, they remain friends, and she continues to serve as a kind of translation mechanism by which the hints and silences of craigslist management are converted into responses suitable for the press. Queries, in recent months, have concerned mostly sex and violence. That the world would expect craigslist to take responsibility for the rare violent criminal who lures victims through an ad strikes Buckmaster as absurd. He points to the thousands of people who die every year in auto accidents. "Does anybody call up the head of GM and say, 'Somebody just got killed using your product? How can you sleep at night? Don't you realize that a person is dead?'"

Buckmaster's dispassionate protest reflects his cast of mind. Emotional appeals are more likely to provoke his skepticism than his sympathy, and when the complaints come from aspiring Internet entrepreneurs he is especially prone to sarcasm. He hears many such complaints, because one of the most curious things about craigslist is that a company designed and run entirely by programmers is so hostile to outsiders who want to pull neat technical tricks to improve the site. A few years ago, independent programmer Jeff Atwood created a service that would allow people to search multiple cities at once or even search craigslist globally. Buckmaster arranged some technical interference to kill it off. Another programmer named Ryan Sit created a service called Listpic, which scraped images from craigslist and dumped them into an interface for browsing: You could scan through all the photos from the apartment listings or see pictures of all the dogs up for adoption. Buckmaster banished Listpic, too.

He had specific objections to both. Listpic ran ads, it put a high burden on craigslist servers, and when he looked at traffic records he noticed that Listpic was being used mainly to enhance enjoyment of the sexy images people posted in their erotic-services ads. Universal search subverts craigslist's mission to enable local, face-to-face transactions; it increases the risk of scams and can be exploited to snatch up bargains, giving technically sophisticated users an advantage over casual browsers. But the very surfeit of these practical objections—many of which probably have technical solutions—hints that the real explanation lies elsewhere, and with a minimum of pressure Buckmaster will state it plainly. It is the same reason that craigslist has never done any of the things that would win approval among Web entrepreneurs, the same reason he has never updated its 1999-era Web design. The reason is that craigslist's users are not asking for such changes.

"I hear this all the time," Buckmaster says. "You guys are so primitive, you are like cavemen. Don't you have any sense of aesthetic? But the people I hear it from are invariably working for firms that want the job of redoing the site. In all the complaints and requests we get from users, this is never one of them. Time spent on the site, the number of people who post—we're the leader. It could be we're doing one or two things right."

This ends the debate for him, but his tone is oddly non-triumphal; in fact, Buckmaster's statement of fealty to users has a weary sound that I don't understand until weeks later. Only after I have spent every spare hour on craigslist—browsing the ads, tracking the spam, reading the help forums, contacting users—do I finally begin to grasp something of his situation. The truth is that a lot of people complain about craigslist. Buckmaster is correct that few of them complain about the design. They complain about spam, they complain about fraud, they complain about the posting rules, they complain about the search, they complain about uploading images. They complain about every way a classified transaction can go wrong. They seldom complain about amazing new features they imagine they might possibly want to use, because they are too busy complaining about the simple features they depend on that don't work as well as they'd like. By eliminating marketing, sales, and business development, craigslist's programmers have cut out all the cushioning layers that separate them from the users they serve, and any right they have to teach lessons in public service comes from the odd situation of running a company that is directly subservient only to the public. Here's the lesson: The public is a motherfucker.

Craig Newmark says that craigslist works because people are good, and he has stuck to this point of view without wavering. Whether you accept it as true will depend on your standard of goodness.

Sometimes entire categories of craigslist are rendered nearly unusable by spam. Con artists prowl the listings, paying sellers with fake cashier's checks and luring buyers to share their credit card numbers. Other evils are more subtle. Business owners whose judgment is distorted by self-interest fail to understand the rules and put the same item in multiple categories or repost it many times a day to insure it stays prominent, crowding out other sellers. A woman listing a car forgets to tell buyers about problems with the title until they've made a long trip out to see it. In all transactions there is a possibility of misunderstanding as well as abuse, and at 99.99 percent perfection there would still be thousands of angry people every month.

Newmark says that craigslist works because people are good. The battle flows back and forth. Captchas—distorted words that can be interpreted by humans more easily than by machines—tamed spam on craigslist for a while. Then it came back full force, not because the spammers had solved the difficult problem in artificial intelligence but because they had hacked an easier problem in global economics. I recently established a friendly email dialog with a young man in Dhaka, Bangladesh, who works on a 13-person team that creates craigslist spam. He fills in Captchas, creates new accounts with masked IP addresses, and posts ads all day long using text from a database provided by his employer, an anonymous spam king. The going price for a spam post on craigslist is about 50 cents, with large discounts for volume. When I told Buckmaster about my new friend, he took the news calmly. "These are technically sophisticated people who take pride in their work, and when we knock them down they don't just decide to go find something else to do. You could say we are breeding the perfect spammer."

Without a computer science research department to work on evil-fighting algorithms, or a call center to take complaints, Buckmaster has settled on a different approach, one that involves haiku. The little poems he has written appear on the screen at times when users might expect a helpful message from the staff. They function as a gnomic clue that what you are seeing is intentional, while discouraging further conversation or inquiry. For instance, start too many conversations in the forums and your new threads may fail to show up. Instead, you will see this:

frogs croak and gulls cry

silently a river floods

a red leaf floats by

Attempt to post a message that is similar to one you've already entered, and this may appear:

a wafer thin mint

that's been sent before it seems

one is enough, thanks

The slight delays in cognitive processing that these haiku cause are valuable. They open a space for reflection, during which you can rethink your need for service. But haiku can't solve everything. Supporting the poems are tens of thousands of users who are willing to devote two or three seconds of time to flag inappropriate ads or forum posts. Too many flags on an advertisement and it will vanish. The staff can lower the number of flags required to vaporize an ad if they want to clean out an especially polluted category, and they can raise the threshold if people grow flag-happy. Users whose listings are flagged off the site get no hint as to what they may have done to attract ire. Instead, they are directed to the "flag help" forum, where pseudonymous volunteers will offer an educated guess while having some fun at their expense. Last spring a baffled user posted a query about why her ferrets-for-sale ad disappeared. Within 60 seconds there was this reply: "Train the ferrets to read the terms of use. Maybe they can help you out next time. Pet sales are prohibited on this site."

An ad can be flagged off the site for any reason. Reject too many people for a job opening and they may flag your ad in spite every time they see it—and every new ad you post, too. Describe yourself as incredibly handsome and cynical date-seekers may flag you as a favor to the innocent. The claim that craigslist, used by millions of strangers, is somehow a democracy begins to be believable exactly here, in the crotchets, irritations, prejudices, and minor forms of harassment that characterize life in a small town where any proposal you make is subject to the judgment of everybody.

Flag something as inappropriate in the discussion forums, where craigslist employees have the final word about what goes, and these lines appear.

thanks for flagging this

staff will look at it shortly

hey, a dragonfly!

Buckmaster's sly haiku evokes an entire scene. Somewhere, at this moment, an innocent party is staring at a computer screen, furious at an offensive remark. Somebody else is fruitlessly trading insults with volunteers on the help desk. A third person is checking the site again and again, looking for a listing that was submitted but never appeared. All craigslist can offer at these moments is a shrug and a joke, in the style of a Dilbert cartoon.

This is old-fashioned. But craigslist is old-fashioned in any number of ways. It relies on email and the telephone in an era of SMS and social networks. It sticks to traceless transactions in an industry that makes its living collecting data from every touch. And just as people who run technical companies are reaching an apex of confidence in their ability to invent new forms of community based on sharing everything, craigslist still treats social life as dangerously complex, deserving the most jaded caution. Corporate isolation, user anonymity, refusal of excessive profit, glacial adoption of new features: These all signal Newmark and Buckmaster's wariness about what humans, including themselves, might do if given the chance. There may be a peace sign on every page, but the implicit political philosophy of craigslist has a deeply conservative, even a tragic cast. Every day the choristers of the social web chirp their advice about openness and trust; craigslist follows none of it, and every day it grows.

Contributing editor Gary Wolf (gary@aether.com) wrote about tracking personal data in issue 17.07

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