Charlie Hit On Me! One Silicon Alley VC’s Quest for Love and Other Startups

Venture man Charlie O'Donnell wants to take you on a meeting.

Navigating such relationships is simply part of the territory, she said. “Initially, I remember it being a barrier for me. But I also found that once you prove yourself and you prove that you know what you’re talking about, it works to your advantage, because the industry is so male-dominated that when a woman comes into the room, everyone pays attention.”

On a recent Friday, Mr. O’Donnell hosted a luncheon at Vapiano’s, the chic Italian eatery near Union Square where he frequently holds court. The lunch had a special purpose: Mr. O’Donnell wanted to meet more women founders as well as introduce them to other women. “I’m interested in creating more opportunities for entrepreneurs, especially women, to connect to investors early to build relationships—less name-dropping pitches, more casual lunches,” he wrote in an email invitation.

Seated against the window in the middle of the gaggle, Mr. O’Donnell thanked everyone for coming and gave a brief speech about how First Round had just invested in two female-led companies, neither of which had been referred by other women. “Stop being competitive!” he said, and asked the attendees to introduce themselves one-by-one. The group ate, drank and chatted for about an hour and a half. One attendee praised First Round Capital to Betabeat for its hospitality toward women, unlike Spark Capital and IA Ventures, which she referred to as “frat houses.”

After lunch, Betabeat asked Mr. O’Donnell privately about the stories we’d been hearing. He vehemently denied he’d ever blurred the lines. (“I take meetings in my office!” he cried immediately, his voice cracking, when we broached the subject of date-meetings.) Over the weekend, he sent out a mass email claiming a spiteful adversary was slandering him to tech journalists—to our knowledge, this individual is his invention—and asking women to speak on his behalf.

Over the next three days, Betabeat received about 30 emails from women (including Ms. Slotnick and Ms. Wulfeck) defending Mr. O’Donnell as a great supporter of women.

“If you’re planning on writing a story about someone in the venture community who has been unresponsive to women, you’re honestly looking at the wrong guy,” wrote Jen McFadden, VP of strategic initiatives at Xconomy. “When I first moved to New York as an entrepreneur, looking to build a network, Charlie was the first one to reach out,” wrote Carmen Magar, a consultant for McKinsey’s Business Technology Office.

Other women shared stories of how Mr. O’Donnell gotten them jobs, encouraged them to start a company or made a crucial introduction. Betabeat reached out to as many of the emailers as we could, although Mr. O’Donnell had instructed them to “ignore any follow up.”

Some told us flatly that Mr. O’Donnell had never made an advance. But upon clarification that the story was not planted by a vengeful enemy of Mr. O’Donnell’s, and that the scuttlebutt wasn’t about his unresponsiveness to women, but rather his overresponsiveness, two of the emailers acknowledged that Mr. O’Donnell “has a problem,” as one put it.

One well-regarded female member of the New York tech scene rushed to defend Mr. O’Donnell, who she considers a friend. “Charlie does have a reputation for asking a lot of women in tech out,” she said in an email. “But he also has a reputation of supporting a lot of women in tech. It’s really important you highlight this. He’s helped me and my female tech friends in a number of ways that have had a profound impact.” Mr. O’Donnell recommended her to an employer a few years ago, introduced her to a crucial female friend and mentor, and advised a friend of hers to fight for a better title.

“And back to him and dates,” she said. “He’s not sleazy about it. If anything, it’s a bit comical because that’s what Charlie does. And that’s important. I’ve known Charlie for years and he’s a good guy who means well.”

It’s increasingly difficult for a single VC to keep dating and dealflow separate, as tech bleeds into every industry and more and more enterprising New Yorkers are seduced by the startup siren song.

“I met someone who was working outside tech, we started dating, and three or four weeks into it she mentions she has a startup on the side,” Mr. O’Donnell told Betabeat. “To be honest, I was hurt, like, ‘I could help you, you know, this is what I do for a living.’ She didn’t want me to think the reason she was interested in me was because of her startup.

“My thing has always been, I’m a person first and a professional second,” Mr. O’Donnell explained. “And these days, tech is so pervasive. I mean, where do you draw the line? Someone with a startup from Conde Nast? People coming from PR and marketing? A company with a website? If you kept your dating life relegated to Luddites, you would get pretty lonely.”