"This is a lifestyle business that got out of control," O'Reilly said when we first met. O'Reilly is 55 and has a craggy, weatherworn face, and he speaks with the warm self-confidence of someone who knows a lot more than you do but is happy to share. "My original business model -- I actually wrote this down -- was 'interesting work for interesting people.' "
When he is not running the sort of business that allows him to work on interesting things, O'Reilly lives a simple but generally splendid life. He owns a pair of white Icelandic horses that he enjoys taking care of; he bakes scones and serves them with a strawberry jam that he makes himself; and he has been happily married for 35 years. His company's headquarters, in Sebastopol, California -- a former hippie enclave that has become a popular destination for wine tours -- sits on a 14-acre apple orchard. He moved the company here from Boston in 1989.
And yet amid all this healthy living, O'Reilly Media has had the kind of impact normally associated with much larger enterprises -- and greater than that of even the most successful hedge fund manager. O'Reilly's work has inspired an entire generation of entrepreneurs -- and his blog posts and essays can push big companies to drastically change course. "Tim really can make a whole industry happen," says Google CEO Eric Schmidt, who credits O'Reilly with helping to popularize the Web and says he expects O'Reilly to pull off the same trick with Gov 2.0. Evan Williams, CEO of Twitter, the hot start-up of the moment, says he owes much of his success to O'Reilly's work. "There's a quick-money unoriginality that is often pervasive in Silicon Valley," Williams says. "Tim has the ability to push people like myself to think bigger and more creatively."
Tech entrepreneurs who have yet to make it big generally regard O'Reilly with something approaching reverence. Darrius Thompson, the founder of OpenCandy, a software company in which O'Reilly has invested, vividly remembers his first meeting with Silicon Valley's unofficial prophet. He was waiting in a conference room in Sebastopol for a meeting with O'Reilly, and he found himself gazing out the window at the apple trees. As if out of nowhere, he saw a middle-aged man with a white beard, who seemed to be floating toward him.
Thompson was hit with a wave of the giggles as he realized that the floating figure was O'Reilly, walking down from a crest beyond the trees. O'Reilly made his way toward the building and disappeared from Thompson's field of vision for a few moments before entering the conference room and proclaiming, "I have no idea why I'm meeting with you, but I feel like I just have to." Thompson, who had always imagined O'Reilly as a sort of mystic, was positively giddy. "Whenever people ask, I always describe him as the Oracle in the Matrix movies," he says. The Oracle is a humble but wise old lady who bakes cookies and has a mysterious ability to predict the future. "That's Tim," Thompson says.
Tim O'Reilly grew up in the Bay Area, one of seven children, to parents who emigrated from Ireland when he was a baby. His father was a neurologist -- O'Reilly fondly recalls getting radioactive copper isotopes injected into his arm as a 14-year-old research subject -- and a deeply religious man. Tim was a voracious reader, of historical novels, of Aristotelian philosophy, and, to his father's horror, of science fiction. At age 20, while majoring in classics at Harvard and studying ancient Greek, O'Reilly rebelled further, marrying a non-Catholic woman seven years his senior. The marriage caused a rift: He did not return home for years, and his parents refused to meet Christina O'Reilly until 1982, when Tim's father was dying of heart disease.
O'Reilly coped by seeking out father figures: first George Simon, a practitioner of a New Age philosophy called general semantics, which stresses a kind of introspective observation. He also became close with his father-in-law, John Feldmann, the founder of a media-buying firm in Los Angeles and the first person O'Reilly encountered who seemed to find business itself to be a worthy pursuit. "We had very different values, but we became close," says O'Reilly. As the young couple struggled to pay their bills by teaching Human Potential workshops, O'Reilly began to see starting a company as an interesting way to live life on his own terms. "I wanted more control of my life," he explained in a company newsletter in 2002. "I wanted work to fit in, not to dominate; to support, not to lead the pattern of my life."
O'Reilly was no more a techie by nature than he was a businessman. In fact, before starting his company, he had never seen a computer. He landed in the field as a favor to a friend, Peter Brajer, who had won a contract to do some technical writing but needed help with the writing part. The job turned into a consulting practice. It was unlikely work for a guy who fancied himself a Human Potential scholar, but it paid well, and he liked the challenge. "Learning has always been something of a drug for me," O'Reilly says. By 1983, he had learned enough about computers to strike out on his own.
For much of the 1980s, O'Reilly & Associates, as it was called, was not so much a company as a collective. O'Reilly hired people like himself: smart, young generalists who seemed as if they might enjoy the challenge of learning something new. There were no full-time employees besides the founder -- just contractors, who would show up at his home when there were consulting jobs. "It was a mix of kindergarten and grownups," says Dale Dougherty, an aspiring writer whom O'Reilly brought into his tribe in 1980 and who would eventually become a 15 percent partner in the business. (O'Reilly owns the remaining 85 percent.) "We had an aversion to the business world, and Tim had this alternative perspective that was very attractive," Dougherty says.
This is not to say that O'Reilly was undisciplined. Christina O'Reilly recalls that her husband was constantly on the phone with her father, going over the latest numbers, and that he would often work late into the night. "It was hard for me," she says. "It was so different from my image of where I thought we were going. But Tim was following his inner talents." O'Reilly never raised outside capital; he funded his projects through profits. "There is a wonderful rigor in free-market economics," he wrote in an early company manual. "When you have to prove the value of your ideas by persuading other people to pay for them, it clears out an awful lot of woolly thinking." Just in case anyone was worried the boss had lost his touchy-feely touch, he went on to compare free-market economics with the poetry of Alexander Pope.
