Rachel Sklar Tries to Become a Social Media Entrepreneur

It was happy hour at the Thompson hotel on the Lower East Side, and Rachel Sklar — entrepreneur, networker, relentless promoter of women — was hoisting herself onto the bar. In one hand, she held a silver ice bucket; in the other, a glass of Champagne and an iPhone.

About 40 women had gathered on a cool April evening to celebrate TheLi.st, an e-mail listserv and Web community that Ms. Sklar founded three years ago to help women in tech help one another. Thanks to an infusion of cash from the Knight Foundation and some angel investors, TheLi.st was about to become an actual for-profit business, a would-be cross between LinkedIn and Facebook for women who will pay for the chance to connect with others like them. Think binders not just full of women, but assembled and read by them.

Throughout the evening, Ms. Sklar, 40, had asked the women to submit written notes on how TheLi.st had helped their careers, for a chance to win prizes (like bags full of cosmetics or T-shirts).

“TheLi.st helped me realize the significance of my company’s progress at an important time,” Ms. Sklar read from a torn bit of paper. “Claire! Oh, Claire went for dinner. But she won a beauty bag.”

In the world of Ms. Sklar, all women working in tech (or media, or politics) are winners, even if they have a problem with her. As long as they are succeeding, she can use them as evidence — data points, she might say — that women deserve to be more frequently hired, funded and featured on the supposedly meritocratic tech scene.

“All I need is for you to be awesome,” she said in a telephone interview. “Then I can wave you around as an example of women who are amazing, who get stuff done when I come up against the people who say, ‘Oh, we tried really hard but we couldn’t find any qualified women.’ ”

Fast-talking, witty and irrepressibly enthusiastic, Ms. Sklar inspires a strident loyalty among many in her orbit. At the party, nearly every woman had a story about Ms. Sklar brokering introductions that proved crucial to her career.

“I first met Rachel at a happy hour drinks, and it ended up leading me into this group of women that has literally changed my career and my life,” said Callie Schweitzer, director of marketing and communications at Vox Media and a recurring presence on “30 Under 30” lists.

“I had nothing to offer her,” said Jocelyn Leavitt, a founder of Hopscotch, an iPad app that helps teach children to write code, “and she was just like, ‘Come with me, let me introduce you to these people.’ I didn’t know anything about anything about tech.”

Stacy London, a host of TLC’s “What Not to Wear” and a founder of StyleforHire.com, said she had started “stalking” Ms. Sklar because she found her Twitter feed (39,000 followers, nearly 50,000 tweets) so informative.

“When I launched my tech company and was looking for like-minded women,” Ms. London said, “she hooked me up with everyone.”

And on and on and on.

But how did Ms. Sklar, who has spent far more time writing musical theater lyrics than source code, become the unofficial yenta for New York women in technology?

It is a long, zigzagging tale, full of ambition, happenstance, heartbreak and summer camp.

Born and raised in Toronto, Ms. Sklar dreamed of a life in the theater. (In 1994, as a drama instructor at her childhood summer camp, she became, as far as she knows, the first person to stage a theatrical version of “Grease 2.”) After college, she applied to the New York University Tisch School of the Arts musical theater writing program, but abandoned her application when the University of Toronto law school accepted her. “I didn’t actually want to be a lawyer,” she said, but “this was something my parents thought would be a prudent move for me.”

Still, the experience would prove formative. “Law school and summer camp are the two experiences that inform pretty much all I do,” she said.

A corporate-lawyer gig eventually brought her to New York, where she decided to indulge a lingering interest in journalism. Through a combination of Mediabistro classes and persistence, not to mention a tireless capacity for socializing, Ms. Sklar rose from FishbowlNY blogger to a founding editor at The Huffington Post and Mediaite.

Her crowded calendar and outsize personality made her a microcelebrity in certain circles, featured frequently (if not always flatteringly) in Gawker and The New York Observer.

She is, by her own admission, a relentless starter of projects. In 2006, HarperCollins contracted her to write a book tentatively titled “Jew-Ish: Who We Are, How We Got Here, and All the Ish in Between.” On her 36th birthday, she formed Charitini.com, which encouraged people to donate money to charity in lieu of buying birthday drinks for friends.