But what happens with 23/6 will be an important harbinger of things to come; it was repeatedly pitched to me as where the CollegeHumor audience would go when they outgrow CollegeHumor, but so far it seems that where the CollegeHumor audience goes when they outgrow CollegeHumor is, in fact, CollegeHumor. (Mr. Van Veen says his readers’ average age is now 28.) 23/6 is also not housed in the company’s shiny new headquarters; it has an office in SoHo, down the hall from the Huffington Post, with which it has a partnership, and from where it seems to be getting most of its traffic, thanks to outbound links on the site.
IAC’s other original content site is the e-mail newsletter Very Short List, which sends out one item—a DVD, a book, an online video—per day to a young NPR demographic. Started by Kurt Andersen and IAC’s head of original programming, Michael Jackson, and now overseen by a single manager and an editorial advisory board, VSL is a personal favorite of Mr. Diller’s. “No exaggeration, since VSL started [in September 2006], I’m sure I have ordered more than 30, probably less than 50, items,” Mr. Diller said. “Without VSL I would be much diminished.” But just as 23/6 is kind of an ersatz Onion or Daily Show, so VSL is kind of an ersatz Daily Candy for smarter people and a national audience. And though its earnest general manager, Gary Foodim, assured The Observer that plans are in the works for additional brand extensions (he declined to be more specific, though he hinted that the site might branch out into, say, specific e-mail lists for music lovers, film enthusiasts and the like), it remains to be seen whether VSL will ever be more than a quirky curator.
And so that gets to the question of influence, and whether Mr. Diller and Mr. Jackson will be able to create from scratch the type of online content phenomenon that will make the kind of cultural impact that it seems Mr. Diller still craves. “In terms of your target market, you want to be a part of their conversation,” Mr. Jackson told The Observer. And it’s that kind of measurement, the kind that is related yet also divorced from financial statements, that right now seems most elusive.