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.Link
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.'"