Sophomoric? That's The Idea

Ricky Van Veen has an important question for his lawyer, and that's why he is diving for the phone. He and his staff have just dreamed up an advertiser-supported contest. The prize: free plastic surgery. "Is that legal?" he asks General Counsel Josh Sussman excitedly.

After a pause, Van Veen blurts: "Oh, Sussman, lighten up!" And then, amid laughter: "O.K., I'll take that as a yes!"

Van Veen is editor-in-chief of CollegeHumor.com, a media play single-mindedly devoted to the (sophomoric) collegiate mind, and he's co-founder of its parent company, Connected Ventures. He and his pal, company President Josh Abramson, launched CollegeHumor when Van Veen was 18. Today, at 26, he is the oldest of the partners. They are all well-scrubbed and ridiculously good-looking. Last summer, Barry Diller's IAC bought the lion's share of Connected in a deal that valued the company substantially north of $20 million. Says Diller: "[CollegeHumor] is not our tap dance." (That is, something IAC might have "naturally" hatched.) "But it's something we can participate in and learn from." All of this good fortune, obviously, makes Van Veen and his partners despicable. That they're also remarkably unaffected, smart, plainly enthused, and generally hilarious only makes it worse.COLLEGEHUMOR IS SO FOCUSED that, aside from the snapshots of bikini-clad coeds, it may be wholly incomprehensible to the over-40 set. But it's also a bona fide business. Van Veen rang Sussman during one of his frequent meetings with editorial- and ad-side employees in which they brainstorm video spots resembling the site's own short-form programming—what Van Veen calls "custom integrations," which can cost over $100,000. High-minded media outlets get hives at such promiscuous commingling of advertising and editorial. But it's hard to get ticked off about church-and-state issues at a site that runs videos along the lines of "Robot Chicken/Star Wars Preview." Despite CollegeHumor's frank raciness, it has helped make ads for its site with some of the biggest brands out there, including Ford (F

) and Procter & Gamble (PG

). (I'm betting those guys won't sponsor the contest idea that prompted Van Veen's phone call, in which one lucky reader will win breast implants for Mom. For Father's Day.) "They're a source for funny pictures of your friend passed out drunk," admits James Kiernan, a Starcom Mediavest vice-president. "But they do a good job of generating unique [ad] ideas." P&G'S Tag Body Spray, a Mediavest client, sponsored a complex "America's Hottest College Girl" competition in which viewers predicted the outcome via March Madness-style brackets.

The first ad CollegeHumor made, Van Veen says, was for a site selling kits enabling consumers to beat drug tests, back around 2001, so the outfit has come a long way. Before its sale, Connected, which also owns clothing company Busted Tees and video-sharing site Vimeo, projected it would gross $10 million in '06. (Diller, Abramson, and Van Veen would not discuss revenue specifics.)

I have no idea whether an advertiser will actually buy any of the ideas I heard concocted by a roomful of CollegeHumor employees—all keenly aware of a reporter's presence. (One suggestion: "We could just make someone smell really, really bad and send them to classy places.") But who knows? In a company like this, the limits are in strange places. One ad exec suggested approaching MoveOn.org with ad-integration ideas. But Van Veen was cool to the notion: "Anytime we do [political content], we get a flood of letters saying 'I come to the site to get away from that.'" The ad guy backed down. "We'll just sell them banners," he conceded. "We don't really want to take a stand on anything." Van Veen nodded. "We can't," he said.For Jon Fine's blog on media and advertising, go to www.businessweek.com/innovate/FineOnMedia By Jon Fine