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"Starting a company was the farthest thing from my mind when I came to New York," says O'Shea 2.0 over coffee at a nearby Starbucks (which serves as the company conference room). RedFilter was, in the parlance of RedFilter, where O'Shea didn't know he wanted to go. But now, he says, "There is no other place I think I'd rather be."
O'Shea sidles up to Stephen Weiss, RedFilter's "editorial director" ever since he handed out all of his first business cards, which said "managing editor." Weiss is a great employee in that he's constantly stoked to be working. He schemes business partnerships, works on the map of the site, writes press releases. "I eat three meals a day at my desk," he says. "It's awesome."
"Okay. Do we want to start this meeting now?" O'Shea asks.
This is the inquisitive management style in action. As a style of authority, it works quite well for him and for the scores of other Internet execs who use it as their dominant mode. This really hasn't changed since 1995: Management rules are as remote as day care to a 23-year-old Net CEO. And, since nobody really knows what they're doing, it's best to listen first, and let consensus rule. The hierarchy is so flat at RedFilter it looks concave.
O'Shea announces that he has called a staff meeting because, he says, "I feel like we're spending huge amounts of time here and its becoming too much like home." O'Shea has been working 10 a.m. to midnight. "I want to find out if you guys feel that way or are you all pretty content?" Only in an Internet start-up would you encounter a boss asking his employees if they want to work less.
"Are you saying we should cut back the hours?" asks Debbie Zambetti, the managing editor and, at 27, the eldest employee.
O'Shea pauses. "Well . . . yes. I think if we're working fewer hours, we'd get a lot more done." This will later be called his "Get-A-Life Dictate."
Michael Keating pipes up. An ex-intern, NOLS alum, and the spunky "director of business development," Keating is that rare being at RedFilter in that he somehow manages to have a girlfriend. "I feel like a lot of our time is symbolic time," he says. "I think we need to get over the cliché that the more hours that you're here, the more you're doing for the company."
The problem is that to restrict symbolic time is to exile members from a belief system, the mythology of how a Net start-up is. In the minds of those knee-deep in milk crates and makeshift workstations, working anywhere elseor at least in any traditional careerisn't attractive because it's not devotional. This is why the atmosphere at places like RedFilter is almost cultish, where three meals a day can be eaten at the same desk and that can be considered "awesome." Where proselytizing is part of your job description. Where Weiss can actually feel "uncomfortable" that his boss is asking him to work less. "I can't tell you how nice it's been for me to have my own schedule," Weiss says. "At my old job, if you came in at 9:40 instead of 9:30, everybody was a dick to you. That was your punishment."
O'Shea closes the meeting by asking that every employee take lunch and dinner out of the office, and that they regularize their schedules to 10 a.m. to 9 p.m.
The following day, at 10 p.m., O'Shea, Keating, Weiss, and Zambetti are still at the office. Why get a life when your future is right there in front of you?
Spy Bar is crowded. It's an open-bar party for UBO.net, the yet-to-launch Urban Box Office Network. Though O'Shea would rather spend his Friday night "lying in bed in a dark room listening to Enya," he and the RedFilter office have dropped bytheir first party of the evening.
Because RedFilter doesn't plan on spending any money on advertising, networking is an essential part of the business. Weiss loves it. "I think for the first time in my life I'm learning how to be friendly and meet people," he says. "Suddenly, I'm passionate."
O'Shea encounters a woman at the bar, who refuses to talk about her own company. It's not clear whether it's top secret or whether she doesn't quite understand what the company does. O'Shea takes his drink back to the dance floor, where the other RedFilter folks are waiting. They dance in a tight circle in the crush; they stick close to each other.
The first generation of start-ups had the luxury of choosing strange names back when there were only a handful you had to remember. The second generation effectively registered the dictionary. The third gen realize they're screwed when it comes to a name. So you make one up, like flooz or Abuzz. Or you start compounding.
"Instead of going out for lunch, I would be at Register.com," says O'Shea. He and 24-year-old Nitin Kumar, RedFilter's VP of business strategy, came up with a list: bigtarget.com, petocto-pus.com, ideogram.com. Filter was a good word, they decided, but already taken. They tried fruits and vegetables, then colors. The word Rhino seemed promisingwhiterhino, electricrhino, petrhino, redrhino, robotrhinobut then Keating came up with "RedFilter." "Eventually you give up," says O'Shea. "You just say, 'Pick something and get on with it.' "