The Father Of Web 2.0

The Trend Spotter
Tim O'Reilly built an empire on computer_ manuals and conferences that make sense of new technologies. Along the way he became the guru of the participation age.
By Steven Levy

Tim O'Reilly likes to walk in the dark. Sometimes after dinner he'll head down the long dirt pathway outside his rambling farmhouse in Sebastopol, California, a post-hippie enclave between wine country and the Pacific Ocean. No flashlight. And on this particular overcast night, with rain dropping from a mossy sky, it's tough to see a thing. But O'Reilly's pace is brisk and optimistic, his feet crunching the dirt as the wiry 51-year-old hurtles himself forward.

As always, he's relying on his radar for safe passage. O'Reilly's radar is legendary. It works on country roads and on the information sea. It told him there was a market for consumer-friendly computer manuals and that he could build a great business publishing them. It helped him understand the significance of the World Wide Web before there were browsers to surf it. And it led him to identify and proselytize technologies like peer-to-peer, syndication, and Wi-Fi before most people had even heard of them at all. As a result, "Tim O'Reilly's radar" is kind of a catchphrase in the industry.

Yet O'Reilly himself has operated for years under the radar. Most nontechies, if they know him at all, know him by the eponymous name of his publishing company. It has a 15 percent share of the $400 million computer-book market but casts a much bigger shadow. O'Reilly books tend to colonize entire sections at Borders and Barnes & Noble, their distinctive cover design as recognizable as the Tide circle on a box of detergent or the Apple logo on the lid of a PowerBook. In serif type over a glossy white background, there is the title, often naming a computer language or protocol familiar to codeheads and gibberish to everyone else ( JavaServer Faces ;Essential CVS ;Using Samba, 2nd Edition ). The illustrations are realistically rendered pen-and-ink drawings of animals.

Now the man behind the menagerie is emerging as a figure in his own right. The conferences he hosts generate a lot of buzz; they also establish a sort of geek's conventional wisdom and build a community around O'Reilly's own hand-rolled view of what's hot or going to be hot. His conclaves come in varying shapes and sizes, from large gatherings like Emerging Technology (ETech) - for which programmers, entrepreneurs, and VCs pack hotel conference rooms every spring - to the intimate Foo (Friends of O'Reilly) camps, which are like pajama parties for propeller-heads. No matter the event, the highlight is usually O'Reilly's opening talk. Hair a bit mussed, eyes gleaming behind wireframe spectacles, dressed in studiously informal garb - khakis topped with T-shirt or fleece - O'Reilly will insist to his audience that "you are our radar; we're just picking it up."

Most recently, O'Reilly's dead-on inner compass led him to anticipate the current stage of the Internet. Powered by the bottom-up nature of sharing and collective action, it's exemplified by such developments as the barn-raising methodology of Wikipedia; group efforts like tagging; open source systems; Wi-Fi; open API's in ecommerce sites like Amazon, eBay, and Google; RSS; the spontaneous connectivity of Apple's Rendezvous; and dozens of other dots that are being connected to fulfill the original promise of the Net. He calls it the architecture of participation. In O'Reilly's world, sharing increases value - so much so that it becomes unthinkable to close off information or to adopt nonstandard proprietary systems. The result is a virtuous cycle where openness becomes the norm, encouraging even more participation.

I got my first O'Reilly briefing on the paradigm of participation last year, at one of his ETech conferences. "We're really at the stage where the Net is the center of everything," he said. "The rules are different. We have a new shift in power." I pointed out that previous ecstatic views of the Internet had been buried under waves of spam, fraud, regulation, and the dotcom disaster. But O'Reilly remains optimistic. "I like to think that even if we make some really bad choices and go down some bad paths, we'll eventually emerge from it."

Then he took a conversational turn that you seldom hear from your garden-variety tech analyst. "There's a wonderful phrase in a different context from Wallace Stevens, talking about a metaphysical view of reality versus the information." From memory, he translated a passage from Stevens' Esthétique du Mal . The key phrase: "Beneath every no / lays a passion for yes that had never been broken."

"I just love that," O'Reilly said, his ever-present sheepish grin taking on a late-afternoon wistfulness. "'Beneath every no lays a yes that had never been broken.' To me, there's this wonderful spirit .… You know, I believe people are fundamentally good and want to find things that make life better for themselves. There are social dynamics for people that work, and there are ones that are pathological. But beneath every no lays a yes that had never been broken. I put my life-faith in that."

And to think we were just talking about Internet protocols. O'Reilly's theories about the next Internet seem on the mark. But the impromptu poetry recital diverted my attention to O'Reilly himself. As it turns out, the levers and pulleys of this new Net neatly reflect the operating principles of the man who helped define it: a philosophy of participation and sharing and a sense that collective action will inevitably accrue to the greater good.

The crucial technologies that make this happen - the digital infrastructure that makes the online world a perpetual swap meet of goods and ideas - are the culmination of all the stuff he's been tracking, supporting, and popularizing for the past 20 years. After O'Reilly hosted his Web 2.0 Conference last autumn (an even bigger confab is planned for this October), digi-pundits began using the term Web 2.0 to describe the growing swarm of applications and Web sites that exploit collective intelligence and participation. But they may as well call it Tim O'Reilly's Internet.

O'Reilly's ability to describe trends in terms of human comity springs from an even deeper source. To find it, I take the road to laid-back Sebastopol, 50 miles north of San Francisco and 35 years back into the cultural past. (Signs at the town line proudly proclaim Sebastopol a nuclear-free zone.) This is the end point of a journey that began long ago for O'Reilly: an epic walk in the dark, if you will, that led to a clearing along the road.

I tour two of the three chalet-style buildings that house his company and have dinner with O'Reilly and his wife, Christina, a vivacious theater person (she is starting her own company, called Light Touch Theater). Then I follow him down some rural roads to his home, set on six acres of farmland. Before I retire to the guest quarters, on the second floor of a garagelike building across a dirt path, he shows me his vast book collection, which stretches across several rooms of his rambling house. I pick up one of the strangest volumes I've ever seen: a dense edition of the journals of George Simon, a little-known teacher of consciousness studies. I borrow the book because it has been painstakingly compiled by Simon's most faithful acolyte - Tim O'Reilly. He tells me that Simon has influenced everything in his life.

Sitting in O'Reilly's kitchen the next morning, I'm eager to discuss it. But no conversation with O'Reilly travels in a straight line. First we talk about music - one of his daughters is in an indie band in Vermont - and we wind up streaming tunes from my PowerBook to his AirPort Express-enabled stereo. Then we sit down at his computer and O'Reilly shows me a custom software visualization he uses to track sales of books and inform his radar on what topics are gaining steam in the infosphere. After that, O'Reilly raises another subject close to his heart: scones. With a little remixing, he mastered a family recipe. He pulls some from the oven. Fantastic.

As I take stock of the cluttered living area with the flooring pulled up (awaiting a renovation that looks like it's not happening in much of a hurry), the music thrumming, and the computer fractalizing complex visualizations of books sales, I get a good sense of who this guy is. But you can't get the whole picture of the guru of participation until you hear about his guru.

George Simon, born in Germany in the mid-1920s, was raised in New York City and wound up in California, where, as O'Reilly says matter-of-factly, "he sold toilet paper." After studying Zen, semantics, and yoga, Simon came up with the idea of building a language for consciousness. He was also a scoutmaster, and in the mid-1960s the boys in his Explorer troop became his students as well. Among them was O'Reilly's older brother Sean, and he brought in Tim.

O'Reilly was drawn to Simon's eclectic philosophy. Bright and curious, Tim grew up in a big family in San Francisco - three brothers and three sisters - and he learned to speak up over a din. But he often found himself at odds with his strict Catholic father. (When young O'Reilly checked out Frank Herbert's Dune from the library, his father said it was sinful for such a large book to be written about science fiction.) Although he didn't buy into Catholicism, O'Reilly absorbed its morality. In high school, an aptitude test even earmarked him for the priesthood. But Tim found himself answering a different calling. Even after the family moved to Virginia, the boys would go back to Simon on their school breaks. Instead of making s'mores around a campfire, they would ponder the weirdly mathematical consciousness theories of their leader. A typical passage from O'Reilly's 1976 notes on Simon's journals:

In the end of Notebook 22, George found that the UZ led on to a C quadrant for HS4. He eventually came to feel that the Z16 covered HS1-3, with a normal HS1 having C and some D, and HS2 having C,D,B and an HS3 having ABCD plus a sense of God.

"When I look back on what Simon wrote, it's such total cultish, wacky stuff," O'Reilly admits. "But the essence of what he had to teach was so right on - the core of how I relate to life came from him." It's hard to extract what that essence is, but reading the notebook the previous night, I saw that George Simon had written: "To know where the path leads means to be able to go there." Underneath which young O'Reilly had scrawled, "Absolutely revolutionary."

"The stuff I did with George," he says, "relates to how I think and operate, the big patterns I see." That includes the pattern O'Reilly talks most about today: the collective nature of the Internet. He believes Simon's vision of a global consciousness is fulfilled by today's Web.

Simon's legacy in O'Reilly's life has a more personal component as well. In 1972, when O'Reilly was 18, his mentor none-too-subtly connected him with another follower, an elementary-school teacher seven years older. This was Christina.

Simon's sudden death in 1973 was a terrible blow to O'Reilly, then a freshman at Harvard. Christina was teaching on the West Coast, and his existence in Cambridge was solitary, dominated by reading. After graduating in three years, he married Christina - causing a serious rift with his father, who didn't approve of a marriage outside the faith. Though O'Reilly was heir apparent to the small but devoted community of Simonites, "I realized I didn't want to make my living being a spiritual teacher," he says.

O'Reilly got a National Endowment for the Arts grant to translate Zen-like fables of the Greek philosophers. Later he wrote a well-received but not lucrative biography of Frank Herbert. By then, he and Christina were living in the Boston area. She wanted a family. He had the knowledge imparted from his guru, his Harvard degree, and lots of stories about Spartans, but none of that would buy a ride on the MTA. Somehow he had to make a living. How could he do that in a way that had meaning? What would be the yes beneath the crushing no?

In 1977, O'Reilly met Peter Brajer, a Hungarian engineer who was taking a class from Christina on nonverbal communication. Brajer, seeking computer-consulting jobs, asked O'Reilly to assist him with his résumé, and the makeover helped Brajer land an offer from Digital Equipment Corporation to write an equipment manual. He proposed that O'Reilly help him, and though O'Reilly had never even seen a computer, they completed the project and then went into business. "I actually feel like I did some of my best work as a technical writer in those early years, because I didn't know anything," he says. "I would just have to read stuff until I saw the patterns."

By 1983, O'Reilly had learned enough about computers to start his own business. He set up shop in a converted barn in Newton, Massachusetts, with about a dozen people, all working in a chaotic open room. "The company then was a loose confederation of people who knew Tim," says Dale Dougherty, who fell into the circle in 1984 and is now O'Reilly's most trusted associate and a 15 percent partner in the business.

What happened in that room was a small revolution in technical writing. The O'Reilly approach was to figure out what a system did and plainly describe how you could work around problems you encountered. "The house style was colloquial - simple and straightforward," Dougherty says. "And the other thing was to tell the whole story, not just what's easy to say."

In 1988, O'Reilly and Associates was producing a two-volume guide to the programming libraries of the X-Windows system; in the process of showing it to vendors for licensing, people kept asking if they could buy single copies. MIT was about to host a conference on the system, and O'Reilly figured he'd give it a shot. "We went to a local copy shop that night and produced around 300 manuals," he recalls. "Without any authorization, we set up a table in the lobby, with a sign saying copies of an Xlib manual would be available at 4:30. By 4 pm, there was this line of 150 people. They were literally throwing money at us, or sailing their credit cards over other people's heads. That was when we went, 'Publishing could be a really big business.'"

As O'Reilly shifted from contract work to the book business, he realized that his guides would have to look appealing in a bookstore. The first designer he hired offered a cover with bright colors and geometric patterns - too slick. One of his writers asked her next-door neighbor, a graphic designer named Edie Freedman, to help out. Freedman thought the baffling names of programming tools - awk and sed and Perl - sounded like weird animals. She created covers that incorporated woodcut drawings of creatures from the Dover copyright-free archive.

The tarsier, with its huge eyes, long bony digits, and head that can swivel 180 degrees, became O'Reilly's unofficial mascot. Freedman chose it for Learning the vi Editor because O'Reilly thought the tarsier "looked like somebody who had been a text editor for too long." Some choices would become legendary, like the hideous Surinam toad on Windows Annoyances .

The books took off, and soon O'Reilly's firm had dozens of guides and a cult following. In 1989, he added a certain mystique to the company by moving it to Sebastopol - not exactly a publishing nexus. The business thrived, partly because of O'Reilly's naïveté. Rivals were selling books to stores at the textbook discount of 20 percent off list price. Not knowing any better, O'Reilly sold his at a "trade discount" of more than 40 percent, a deal that bookstores couldn't pass up. As a result, they were willing to take a chance on more technical tomes they had previously passed on.

But O'Reilly's radar was responsible for his biggest coup. He sensed that the Internet, then still a province of the government and universities, was the platform of the future. Yet there was no documentation for those willing to venture into cyberspace. O'Reilly found his author in Ed Krol, an unknown gearhead who had written an online document titled "A Hitchhiker's Guide to the Internet." Krol took more than a year to expand his short report into a book. Because it had started as a free digital pamphlet, O'Reilly arranged for the second, lengthier part of the book - a catalog of what's on the Net - to be available free online.

The Whole Internet User's Guide and Catalog (1992) became a category-busting best-seller, establishing itself as "a 250,000-copies-a-year thing," O'Reilly says, at least until it became outdated in the mid-'90s. He saw the book not just as a tent pole for his business but as a chance to awaken the world to the Internet. He went on a press tour. He sent a copy to every member of Congress, and was invited to meet with House aides. Before addressing a huge group of them, he was taken aside by the House IT department. "I go into this little room, and it's like Three Days of the Condor ," O'Reilly recalls. "This old guy in a three-piece suit and a cane says, 'We don't want you to get the aides too excited about the Internet, because we're not going to give it to them.' So I went out and got them excited anyway."

O'Reilly was learning how to become a successful businessman without suppressing his open nature. Borders exec Carla Bayha recalls meeting him for the first time at a computer-book-publisher's conference. Seated next to her at lunch, O'Reilly excitedly began telling her all the great ideas he had for next year's list. "I had to shush him up," she says. "All his competitors were sitting at the table!"

At first, propelled by what he calls "daddy-juice," O'Reilly had been trying to make a living for his wife and two young daughters, Arwen and Meara. But as he got deeper into it, he realized that even the jargonesque domain of computer books could be a pathway to something more - that unbroken yes he first learned from George Simon. "People don't care about books," O'Reilly says. "They care about ideas." And no one would have more ideas than O'Reilly about the Internet age that was rapidly approaching.

In the early '90s, O'Reilly and Associates found itself on top of a priceless claim in the emerging Internet gold rush - as not only a guide to cyberspace but an innovator in creating Net destinations. To O'Reilly, the effort was as much about pushing the idea of the Internet - and the changes it could bring to society - as it was about turning a buck. That was perhaps why, despite being among the first to realize there would be Internet commerce, O'Reilly never rose to the top of its food chain.

But he did claim some serious firsts. When someone suggested he start a magazine about the Internet, O'Reilly asked why not start a magazine on the Net? The company's catalog morphed into what was arguably the first portal, the Global Network Navigator. "We were the first people to do advertising on the Web," he says. "I actually saw in 1993 that the ad could be the content, the destination." In a related venture, O'Reilly offered a pioneering off-the-shelf kit called Internet in a Box to help novices make the jump into cyberspace.

GNN also collaborated on a directory of the Web created by two Stanford students, Jerry Yang and David Filo. At one point, they asked if GNN was interested in buying the venture - Yahoo! - outright. "I think they wanted a million dollars, and we didn't have a million dollars," O'Reilly says. (Yahoo! doesn't deny the discussion but says it didn't set a price.)

Nor did he have the resources to grow GNN once the media giants jumped in, so in 1995 he sold it to America Online for $11 million, mostly stock and options. "If we'd held on until the peak, that stock would have been worth a billion dollars," he says.

Still, he has pocketed some nice change over the years by investing in companies that show up on his radar. (As an early funder of Blogger, which Google bought, he wound up with a chunk of pre-IPO stock in the search giant; more recently he's invested in the bookmark-sharing service del.icio.us .) But he's nowhere near as loaded as some others who did well during the boom. "We never had a megascore," he admits. "We could have gone public if we wanted to, but why cash out and get all those headaches?"

O'Reilly's company was hit hard by the crash. In the late '90s, its expanding publishing schedule required a move from cramped quarters in the center of Sebastopol to a brand-new complex down the road. It took six years to complete the project, thanks to a lawsuit filed against the city by locals who saw O'Reilly as more of a modern-day robber baron than as a scone-baking publisher. By the time the new campus opened in 2001, the bubble had popped and book sales tanked. O'Reilly had to fire some 70 people, about a quarter of his staff. "It was the worst I've ever seen him," Christina says. "Service is a big part of who he is - a big goal is to give people jobs." O'Reilly admits that if he'd gone public, "I could have given them comfortable retirements."

The buildings still have almost 30 vacant rooms, as if there's another tenant that hasn't moved in yet, and annual sales are still $15 million lower than they were during the boom. But the titles continue to pour onto the shelves, revealing which languages and apps are au courant in nerdville.

They serve a range of readers, from the gronks who gobble up the code books to the vanilla users consulting the Missing Manual series or general readers who want to know about privacy issues or the history of the Macintosh. O'Reilly also has an online service called SafariU that lets schools and businesses remix their own texts from O'Reilly publications.

The most successful recent venture is a wonderfully retro idea: Make , a quarterly print magazine in the spirit of Boy Scout DIY projects. The first issue, published in February, had articles on doing aerial photography with kites, making your own videocam stabilizer, and building a machine to read the magnetic stripes on credit cards. O'Reilly believes that the urge to hack stuff is "more common than we thought." And it dovetails perfectly with the participation-based Internet he extols. The magazine has already exceeded his goal of 30,000 subscribers.

It's one more confirmation that this is O'Reilly's time, and not just in his professional life. He has always been rooted in his family relationships, and the years that his father refused to allow O'Reilly into his home because of his marriage and departure from the church pained him immeasurably. Ultimately, they reconciled, and at his father's deathbed, O'Reilly tried to explain to the old man that his maverick life - and especially his business - was really about the concepts of goodness he'd learned at home.

His father, who at that point could not speak and had to write his comments on a slate, scrawled what O'Reilly saw as the apology he had waited decades to hear: "I only wanted you to be with us in paradise." Now O'Reilly and his siblings jointly own a castle in Killarney, Ireland, where their father is buried. The seven O'Reilly kids of Tim's generation, and their 39 children, all work on it together. "The idea of a project that brings people together was really what was interesting about it," O'Reilly says. Like castle, like Internet.

Satisfaction also comes from O'Reilly's continuing connection to his other late father, the toilet paper salesman-cum-guru who opened up mental vistas that only recently have reached full fruition in his student - now that the idea of collective consciousness is becoming manifest in the Internet. "The work with George was about the future and the potential of what it is to be human," O'Reilly says. "But here we are. The Internet today is so much an echo of what we were talking about at [New Age HQ] Esalen in the '70s - except we didn't know it would be technology-mediated."

Could it be that the Internet - or what O'Reilly calls Web 2.0 - is really the successor to the human potential movement? If so, the new Esalen is his increasingly fabled Foo Camp, where 200 or so people - a gamut ranging from Amazon.com's Jeff Bezos to BitTorrent's Bram Cohen and random wizards doing VoIP hacks - are invited each year to the underpopulated Sebastopol campus to crash in empty offices or pitch tents in the backyard.

At the Foo Camp in August, O'Reilly opened by asking participants to identify their passions with only three words. After the introductions came a mad rush to a giant poster board to fill up the empty squares with an instant, self-organized agenda. Sessions ranged from "Beyond Python" to "Tele-operated Humanoid Robotics."

Tim O'Reilly's three words? Harnessing collective intelligence.