"I can only connect," she says. "I have no idea what to do unless you tell me what's upsetting you."
Rossi has many friends, many of them famous — Nicole Richie, Soleil Moon Frye, Lauren Conrad and Mindy Kaling, to name a few. These famous pals might have benefited her career, but friendship itself has been her muse.
Rossi, 33, has always been fascinated by young womanhood (which helped define her enormously popular website, Hello Giggles). Maybe it's because she never really experienced it, at least not in the traditional sense. Born in Long Beach and raised in the flats of Beverly Hills, Rossi went to college for exactly one day.
Then she went to work, first for music supervisor/nightlife impresario Amanda Demme, then for Jay Z's business partner, Damon Dash, in New York. She moved back to L.A. to produce The Hills, the landmark reality show that followed Conrad, her friends and frenemies as they navigated the choppy waters of L.A. nightlife. Rossi's role was part therapist, part social secretary and part best friend.
When she decided she wanted to start her own website, her idea was to create a Funny or Die for women. Her partner, Gawker blogger Molly McAleer, convinced Rossi that the site should tap into the pool of young female writers who write on platforms such as Tumblr.
At the time, Rossi was taking a dance class in the San Fernando Valley. One of her classmates was Zooey Deschanel. One day after class, a then-unemployed Deschanel walked up to Rossi and said, "This is weird, but would you like to go to lunch?" At Hugo's, Rossi told Deschanel about her new project and the actress responded: "Great, I would love to do that with you."
This was in 2011, when the Internet was full of snark and sass and meanness. Hello Giggles would be different, in part because Deschanel was afraid of the Internet and insisted that their site, an incubator of young talent, be safe and inclusive.
"Zooey set the standard and then Molly set the quality," Rossi says.
But Rossi, who grew up devouring Nancy Drew and Baby-Sitters Club novels, imprinted her own personality on the site, which celebrates women, young adulthood and, above all, friendship. There were few posts on fashion. Instead there were ruminations on body image and modern feminism, essays on growing up and lessons learned.
The site started small, in Rossi's apartment with a couple freelancers. Four years later, Hello Giggles has 26 employees, a chief operating officer, venture capital money and a new, 5,500-square-foot office downtown with windows that you can write on with dry erase markers. Traffic to Hello Giggles is on par with Gawker's women's site, Jezebel (each gets about 12 million unique visitors a month).
And if the site is entering maturity, so is Rossi, who just published her first novel, A Tale of Two Besties — and whose newish responsibilities as a boss no longer allow her to hang out with friends for four hours at a time.
"I actually said the other day, 'Oh my god, I think I'm growing up,'" she says. "I'm losing that friendship bracelet–world mentality."
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