Last summer, Sir Richard Branson, the entrepreneur behind the Virgin companies, invited a few of his friends–luminaries such as Archbishop Desmond Tutu, Jimmy and Rosalynn Carter, Peter Gabriel, and Google cofounder Larry Page–to be his guests at Necker, his private island in the Caribbean, for a few days. Branson also summoned Jimmy “Jimbo” Wales, the creator of Wikipedia, the free and wildly popular online encyclopedia that’s open to anyone to rewrite and edit. Now, when Wales talks about that heady week, he’s quick to mention how he beat Page in a sailing race around the island. But Sir Richard raised the stakes when he invited the Internet boys to join him in a more thrilling and dangerous pursuit: kite surfing.

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If you Google “kite surfing,” the first search result is a Wikipedia article that describes its kicks–jumping and flying off the water’s surface through the open air, towed by a powerful kite at speeds of up to 50 kilometers per hour–as well as its hazards: “A bad landing may result in hard impact leading to serious injury or death.” While Page, a veteran kite surfer, showed off his impressive jumps, the envious Wales took novice’s lessons from Branson’s staffers. When you first learn to kite-surf, you spend a lot of time “bodydragging”–the kite pulls your dangling torso roughly through the water. It’s humiliating, but Wales persisted. “I can’t actually say I can do it, but it was fun trying,” he says. “It seemed easier once I was trying to do it. It was like, Oh, I kind of see how this works.” But then the weather turned foul, and Wales wasn’t able to go out on the water. He left the island without matching Page’s feats. A few months later, in December, Wales took a shot at Google, telling a London Times reporter that the dominant Web search engine produced too much “spam and useless crap.” His point was that shamelessly self-interested hawkers routinely outsmart Google’s system to get their commercial Web sites posted high up in the search results, outranking ones that might prove more informative and useful. Wales revealed that Wikia, his for-profit Silicon Valley startup, was working on Search Wikia, which he touted as “the search engine that changes everything…. Just as Wikipedia revolutionized how we think about knowledge and the encyclopedia, we have a chance now to revolutionize how we think about search.” Wales envisions large numbers of real live people–the kind of fervent volunteer brigade that edits Wikipedia–intervening to improve on the machine-generated results that we’re used to from Google. “Help me out, spread the word,” Wales posted on Wikia’s Web site, and quickly his new search effort received 4 million mentions online and attracted its first 1,000 volunteers. Although Wales says it will be another year or two before they will have a viable search engine up and running, he’s publicly previewing a crude, preliminary version this spring. Google, in response, has confidently taken the high road. “Google has maintained a substantial lead in search quality for the past five years,” said a spokesperson, “and we are committed and focused on search to ensure Google continues to offer the best search experience available.” But the move has stirred considerable ferment in the rest of Silicon Valley. Is Wales inspired? His stewardship of Wikipedia certainly imbues him with credibility. He has sustained the culture of the largest mass collaboration attempted yet through the Internet. The sheer scale of Wikipedia, founded only six years ago, is astounding: more than 280,000 current volunteers creating and editing more than 5.3 million encyclopedia entries in more than 100 languages. It would be foolish to underestimate the man who founded the sixth-largest Web site in the world.

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Or is Wales delusional? Wikia is a startup with few employees and $4 million in funding from private investors, competing against the most extraordinary corporate success story so far in the Internet era. Google controls nearly 50% of the U.S. search market. It has already defended itself against multibillion-dollar assaults from Yahoo and Microsoft . It had revenues of almost $10 billion last year and earnings of a cool billion last quarter alone. It can tap the energies of 10,000 employees, including two still-young, still-brilliant cofounders. And it holds more than $10 billion in cash and marketable securities and stock worth about $150 billion. In Silicon Valley these days, it seems that everyone wants to work for Google or to sell it their startup, as YouTube recently did for $1.65 billion worth of stock. Despite its wealth and mystique, though, Google is surprisingly vulnerable, creating an opportunity for a guy like Wales. Google doesn’t have an effective method of locking in its customers the way earlier info-tech leaders did: Once you’re using Microsoft’s operating system or Oracle’s database, switching to a rival’s software means a considerable cost in time and money, as well as untold aggravation. But trying out a different search engine than Google involves no more than typing in a different short word in the address bar of your Web browser. What’s more, studies show that users are disappointed with the current state of search and consider Google hardly any better than its rivals. In a blind study by the French linguistics scholar Jean Véronis and his students, Google and Yahoo tied for user satisfaction with their results, both scoring an embarrassing 2.3 out of a possible 5. About 28% of the time, users thought that all the search results they received from both engines were “totally useless.” They gave fairly low marks of 2.8 and 2.9 even to the very first links listed by Yahoo and Google, respectively. About a quarter of the time, they didn’t find what they considered to be even one good result from either search engine. Just how is Wales going to do it? Even he doesn’t really know–at least not yet. That’s part of the process of mass collaboration. When Wales began his encyclopedia project in 2001, he started by commissioning articles from experts and subjecting them to peer review before he hit on the much faster approach of letting anyone write and edit. And he dealt with the unfolding problems, such as accuracy and vandalism, as he went along. This time around, with Search Wikia, he’s starting out with an intriguing idea and an invitation to the Internet community to take part in shaping it in unexpected ways. The community has responded quite enthusiastically so far, catching even Wales by surprise. “I just thought we’ll put a couple of developers on it and kind of play with it on the side and see what comes up,” he says. “But now there’s a huge developer community that’s really interested.” As Gil Penchina, Wales’s handpicked CEO to lead Wikia, says, “Since the news leaked out, people have been lining up, saying, ‘I’ll clean the toilet bowl, let me in here.'” And the caliber of the toilet cleaners is very strong: They range from Mark Schellhase, age 13, a whiz kid in Gaithersburg, Maryland, to William Surowiec, 64, who loves programming and did it every day through a 42-year career until his position at a big New York publishing company was cut last summer. Surowiec considered retirement, he says, but “bluntly, it sucks. I want to code. I want to be in the action, to be part of a team competing to do something interesting and do it well.” In between, there are PhD students, such as Gérard Dupont in Rouen, France, who’ve been working on search technology. “When they finish their dissertation, they will probably be looking for a job at Google,” Wales says, “but for now they don’t have access to the real cutting-edge research there, so they’re happy to meet up with people and participate in an experimental project. So that’s kind of cool.”

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Wikipedia had 164,675,000 unique visitors in December 2006, ranking sixth on the web and reflecting a 107% growth rate over last year More than 75,000 Wikipedians have edited 5 or more articles in the last month (as of October 2006) (Source: comScore Media Metrix) Wales also has the somewhat radical idea of banding together Google’s rivals to upend the search giant. “The other thing we’re looking to is some of the second-tier search companies,” he admits. “We’ve talked to–I can’t say who–different people, asking, would they be better off participating in a project that helps quality search results to become a commodity?” The idea is that no one on their own can compete with Google’s resources to catch up in terms of the quality of search, but together, they could render that moot and compete on brand and user interface. Early this year, Wikia was rumored to be in discussions with Ask.com. Wikia will need all the help it can get, because building a great search engine is far more daunting than building an encyclopedia. Major players such as Google and Yahoo index tens of billions of Web pages. (Google used to post proud signs proclaiming the actual number it had served–like McDonald’s with hamburgers–until that figure became too impossibly large to keep track of with any kind of reliability.) Searching the Web takes computational brawn, which is why Google runs huge numbers of networked computers in vast warehouses. It takes exceptional brainpower, too, which is why Google has lured an impressive cadre of top computer scientists to write the sophisticated algorithms, that make the difference between really useful results and crap. “Jimbo Wales is completely underestimating how hard it is to do search,” says Danny Sullivan, the editor-in-chief of SearchEngineLand.com. Wales will need to duplicate what Google has already done before he can try to improve on it. He needs machines to generate search results before humans can look them over and tweak them. He’s starting out by relying on the free open-source search projects Nutch and Lucene, which have successfully replicated a lot of the vital under-the-hood mechanics. But he’s going to need more, which is perhaps why Wales takes the long view. “If you’re growing community, a healthy community Web site, it takes time,” he says. As a personality, Jimbo Wales, 40, is full of fascinating contradictions. The biggest mystery may be how a former options trader and self-professed follower of objectivism, the philosophy of Ayn Rand–a combative elitist who glorified the heroic, capitalistic individual and denigrated the envious, ignorant masses–became the guiding force behind a collectivist Web site that’s often criticized for its “mob mentality.” Wales is such an objectivist that his daughter Kira, 6, was named after the heroine of Rand’s first novel, We the Living. Yet he has been criticized for being the Web’s equivalent of a Maoist, and he playfully likes to wear red silk Mao jackets at public appearances. During my time with Wales, he slowly reveals the different layers of his personality: At the base, there’s the gentle geek who uses the word “fun” or “funny” in nearly every paragraph and seems genuinely driven by the pure intellectual challenge and the public-spirited idealism of his projects. He carries a Sidekick , because “I’m kind of a noncorporate-y kind of guy. It just seemed so–I don’t know, I’d have to get a suit if I had a BlackBerry .” Yet he says this while wearing a dark chalk-striped blazer, very Wall Street, having just come from an appearance on MarketWatch. (He did subvert the look with a purple turtleneck.) He checks email and instant-messages obsessively, even in the moments when he’s waiting for the barista to make his coffee. “If I’m stopped at a red light, I’ll look at the news headlines, although I try not to do that too much. My wife doesn’t approve of that kind of thing in the car while driving.” In this way, he’s like his techno-nerd friend Craig Newmark from Craigslist (who gets wide-eyed with awe about Wales, saying “Craigslist is for the moment, but Wikipedia is for the ages”). But unlike Craig, Jimbo is socially comfortable and adept, a quiet charmer and effective communicator.

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But that’s just the start of his apparent contradictions. Jimbo is wealthy, having made enough money on Wall Street by his early thirties that he wouldn’t have to work again, yet he’s a confessed cheapskate who lives in a modest single-story house in St. Petersburg, Florida, and he has spent the past half-decade working for nothing for a Web site dedicated to free access to human knowledge. He’s both an outsider and insider. “All of our social world revolves around my daughter,” he says, but “professionally, I know more people in London than in Florida.” And he clearly relishes consorting with celebrities from business, politics, and popular culture, as he did that week on Richard Branson’s private island: He was thrilled when his daughter flew on a helicopter with the Carters, and the ex-president said that he used Wikipedia every day. Wales talks about Wikia and his new search project as if it’s his rich-man’s toy, his version of playing golf. “As long as it’s fun, I don’t care,” he says. “As long as we’re having fun,” he repeats, “and it’s an interesting project and once people are interested, let’s take a shot at it. Search can pay for itself even if you don’t become the market leader. Well, why not?” Go deeper, though, and he betrays hints of the tenacity and ambitiousness of a true mogul. When Wales talks a lot about the public good and just having fun, one can forget that he’s the founder of a startup that runs paid advertisements alongside the content created by its communities. Although Wales still sits on the board of the nonprofit Wikipedia Foundation, he gave up its chair to focus on Wikia, a separate and independent for-profit company, working with Penchina, who used to run eBay’s European businesses. (Penchina is more of the inside-operations guy, while Wales is the public figure.) With Wikia, which launched in 2004, Wales has expanded metaphorically from the encyclopedia to a library full of other books, all created and edited by online collaboration with free tools and Web hosting from the company. Its ad-supported sites get into much greater detail about specific topics: Muppets fans, for instance, have contributed more than 13,000 articles to Wikia’s Muppets site. Ironically, Wikia relies on text ads generated by Google, so Search Wikia is biting the hand that feeds it (Wikipedia, for its part, gets about one-third of its traffic from referrals from Google’s search engine). Google Is More Vulnerable Than You Think… Only 21% of professionals always feel that search engines understand their queries 10% always find exactly what they want on the first attempt …But Without a Viable Alternative, People Bang Their Head Against the Wall 93% of users tend to search again using a new query with similar meaning at the same search engine rather than switch to a new one (Source: Convera, November 2006) Even though Wikipedia gets the media attention, Wikia is growing even more quickly and could become the bigger creation. Already Wikia’s 500,000 articles makes it bigger than the French Wikipedia, and its momentum will soon help it surpass the German Wikipedia and will then put it in contention with the English Wikipedia. “Jimmy is a fiercely competitive guy,” says Don Tapscott, who got to know Wales while researching his best-selling book Wikinomics. “And he’s a staunch defender of his ideas.” After all, Wales has never cooperated with China’s efforts to censor Wikipedia even while Google, Yahoo, and Microsoft have all acquiesced. People’s faith in Wales stems from his often-overlooked leadership abilities. “Jimbo really left his hands off the typical control knobs that a manager would use to control a company [with Wikipedia],” says Henri Poole, a veteran Web entrepreneur who’s on the board of the Free Software Foundation and knows Wales personally. “He’s a cyberspace diplomat and a master at it.” As evidence, Poole says that one reason for Wales’s success at Wikipedia was how he let the Wikipedians create different types of governance structures to fit with the local cultures of the different countries around the world. “He has the confidence to let something go,” adds Tapscott. Wales’s success or failure will come from how well he encourages his community’s inventiveness. Wales is a champion of the open-source movement’s public-spirited idealism, and he emphasizes that Search Wikia’s inner workings will be “transparent” to everyone–rather than secretive, like Google’s. He views it philosophically, and much like Wikipedia, saying, “This is fundamental, basic information about the world. It needs to be neutral, and there needs to be an accountable, transparent, public dialogue about how it’s created.” If the processes were open to inspection and debate, Wales feels that people would put more trust in the results. “I trust Google reasonably well,” he says, “but that’s like saying you have a favorite politician. I trust this politician, but I still want the city council to meet publicly. I still want a certain transparency in how government is run, even if you trust the person who’s in charge now.”

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It’s that sense of grandiose mission and deep-rooted belief that may make Wales the most dangerous of the many challengers in the search business. Between 2002 and the third quarter of 2006, more than 170 search startups received more than $1 billion from venture capitalists (they’re so pervasive these days that Wikia’s headquarters in San Mateo, California, happens to be located downstairs from Oodle, another search startup). Many of those newcomers are simply hoping to get a tasty crumb of the $20.7 billion search advertising pie. The most promising strategy seems to be focusing on a niche that Google overlooks–Zillow, for example, specializes in searches for house-sale listings. Wales, for his part, is trying something much bigger and more ambitious. He has already amassed an army of volunteers who are contributing to Wikia and who can now be leveraged for the search project as well. But it’s not the first time that a “people-powered” search engine like this has been attempted, and the others have mostly faded or languished in obscurity–Infrasearch (backed by Netscape cofounder Marc Andreessen), Magellan, the Open Directory Project. Yahoo, of course, had hundreds of employees who categorized Web sites in the ’90s, but the Web quickly became so enormous that Yahoo’s people could review only a sliver of it, a problem that will surely be faced by Wales’s Search Wikia–and one reason Google’s approach won out. Google’s genius has been that its machine-muscled method reflected a lot of good information about how real people were reacting to its search results. Google’s brightest innovation, hatched by cofounders Larry Page and Sergey Brin while they were still graduate students at Stanford, was for search engines to rank Web pages based partly on the number of other pages that linked to them, using that as an indicator of relevance, usefulness, and importance. But that has been an easy game for hucksters to play, since it costs very little to create countless dummy Web pages solely intended to generate links to the commercial sites you want to promote. This is why search results can so often disappoint users. Silicon Valley insiders whisper rumors that the “link farm” problem recently forced Google to move away from relying so much on links as a major influence on search rankings. Instead, it’s reportedly focusing on analyzing what people click on and the content of Web pages. The latter is exactly what Wales believes people can do better than machines. If Wikia can find a better way, there’s a good chance that it can gain real popularity. But that’s a big “if,” says Peter Wayner, the author of Free for All, a history of the open-source software movement. “The fascinating question is, How are you going to do it better than Google? If you put humans in the loop, maybe that will stop the gaming. But what if the humans are corrupt? Humans are as likely to be biased.” Wales, for his part, has tended to downplay the spam problem he might face, without offering a concrete plan beyond relying on the community to figure it out. His Wikipedia experience might be enough. “The way Wikipedia deals with saboteurs is to change them, not to crush them,” says Tapscott. “They find something good about them and embrace it. This attitude is what you need to make this work.” No matter how much anyone believes that Wales may be engaged in a quixotic enterprise, they’re rooting for him. They want an alternative. “Someone should try to make the next big leap in search,” says Dave Winer, who pioneered the popular RSS feeds for media distribution over the Internet. “Even if there are reasons to believe that Wales’s effort will fail, I’m glad he’s trying. We need more people who don’t accept the hype and are willing to try to get to the next level.” Great business leaders do fall. Remember when IBM reaped 70% of all the money spent on computers? When GM controlled 60% of the U.S. auto market? When Sony , not Apple , dominated portable music? In the grand scheme of things, it wasn’t that long ago that the war for online dominance was between CompuServe and Prodigy. And it was thought to be a winner-take-all market. “The Internet just blew that wide open,” says Wales. “Actually, I suspect that we probably dodged a bullet there in the sense that the Internet just existed and some of the players realized, if it’s winner take all, we’re better off letting our customers talk to each other over the Internet. There’s a certain compelling logic to it.”

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Rome fell, the British Empire fell, and it’s possible that even Google will fall too. This time, when Jimbo Wales tries to compete with Larry Page, he may get body-dragged relentlessly, or worse, slammed fatally against the rocks. Or he might jump and fly gloriously through the open air. Either way, it’s going to be a wild ride.