Rachelle Hruska planned on becoming a child psychiatrist. But in 2005, she decided to come to New York and became a nanny, then an assistant at a capital management company. And now she's a successful Internet entrepreneur. Hruska's founder and editor of GuestofaGuest.com , an eclectic site that The New York Times once described as a "an online New York social diary and calendar for 20-somethings." The site went live April 2008, broke even in June of 2009, and has been growing ever since, recently expanding its coverage to Los Angeles.
The title is a cheeky reference to its summer-in-the-Hamptons origins, where "everyone's a guest of a guest," explains Hruska -- that is, invited to share a room in some house that was rented to begin with. As the site expanded to cover the Manhattan socialite scene, the title took on a second meaning. As Hruska and her staff flitted from one soiree to another, the site's readers became digital plus-ones getting a glimpse behind the red-velvet ropes. They cover about eight to ten events nightly. "I don't go to every single event," Hruska says. "I'd probably be dead by now."
GuestofaGuest was co-founded with Cameron Winklevoss, recently immortalized in The Social Network. Winklevoss, whom Hruska dated when she first moved to New York, financed and developed the site's first incarnation. He remains the site's publisher, consulting with Hruska daily. ("The Facebook thing obviously is something Cameron's trying to move on from," she says, referring to the movie. "We don't bring it up in conversation ever.")
As for the site's future, Hruska is sure she wants to grow it -- even if she isn't sure in which direction. Depending on how the L.A. site fares, she might follow a Thrillist or Curbed model of a national network of local coverage. Or maybe a Gawker Media approach, with different sites focusing on different topics (fashion, for instance), might better suit. "One thing Cameron and I are both good at is acknowledging we don't really know what we're doing." Hruska says she uses other media entrepreneurs like Nick Denton and Lockhart Steele as guides. —David Zax