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.

To hear the city’s female entrepreneurs tell it, an ambiguous date-meeting with Mr. O’Donnell is almost a rite of passage—like living on ramen while you launch your first app. One female founder recalled a recent girls’ night out with a mix of tech and non-tech friends, during which Mr. O’Donnell came up in conversation. “We were talking about how he was trying to hit on [one female entrepreneur who was present],” she said, when one of the women who did not work in the tech scene recalled a similar situation she’d encountered in college years ago. “She said, ‘I was the president of my investment club and this guy came to speak. He was bald and he worked at GM and he came up to me afterward and asked me out to dinner, and made it seem like it kind of was a mentoring thing, but it was a date, and it was really weird and really uncomfortable.’” The guy turned out to be Mr. O’Donnell, too. Of the seven women at dinner, the source said, five had stories about fielding Mr. O’Donnell’s attentions.

Not that attention from a young, long-lashed VC is always a bad thing. “My friends and I sometimes joke, we don’t always mind the ratio,” admitted Sarah Wulfeck, a director from a digital agency, referring to the gender disparity. “I think lots of women in tech feel that way sometimes, too, if they’re honest. What do you do at an event with a lot of smart young professionals who are drinking and schmoozing and talking about money and dreams? Human social behavior is what it is.”

We turned to Nancy Slotnick, who works as a dating coach and is the founder of Facebook application MatchMaker Cafe, for perspective on how personal the professional should get. “I’m kind of all for flirting,” she said. “I think women don’t do it enough!”

If you’re not sure whether you’re on a date, just ask, she said. “There’s so many situations where you could be trying to figure out, is this a date or not a date,” she said. “These days, people work so much, especially entrepreneurs, and if you’re trying to meet someone for dating, you have to do a fair amount of switch-hitting.”

Many New Yorkers complain about the murkiness of modern dating rules, but the issue is particularly dicey in the tech scene, which feels morally tormented by its gender imbalance. Between panels everywhere from South By Southwest (“Has The Glass Ceiling Ever Smacked You In The Butt?”) to the White House (with Valerie Jarrett), countless stories in the tech press (“Not Enough Women In Tech? Stop Blaming the Men,” “Tech Really Is A Man’s Man’s Man’s World”), and awareness campaigns like Change the Ratio, handwringing is endemic. “Nothing seems to irritate nerds more than the idea that they’re oppressing people,” one techie mused recently on a forum discussion about women in tech. “It probably has something to do with the fact that so many of them were picked on growing up.”

Most women in tech try too hard to separate work and romance, in Ms. Slotnick’s opinion. But she acknowledged that things can get complicated when the players are a founder and a VC.

“That’s not a switch-hitter situation,” she said firmly. “That’s a situation where you have to choose: date the guy and put the situation on hold, or if you want to get his money, focus on that and put the dating stuff on hold.

“But that doesn’t mean you can’t flirt,” she added.

But in light of his influential position, Mr. O’Donnell’s flirtatiousness has come close to getting him in trouble. One woman complained to Josh Kopelman, the managing director at First Round. When Mr. O’Donnell was confronted, he tried to guess who had complained—and guessed wrong. Another well-connected woman in the New York tech scene said she has spoken to Mr. O’Donnell about toning it down. “A few women who have offered their guidance and feedback to him only to be met with defensiveness and a refusal to hear it,” she said.

What seemed to grate on many of Mr. O’Donnell’s targets was the sense that they’d been subjected to a romantic version of the bait-and-switch: expecting a meeting, they’d found themselves on a date. We heard other complaints, similarly mild—flirting over Facebook, flirting over latenight Gchat, flirting over email. A male founder-turned-VC was particularly irked because Mr. O’Donnell had hit on his wife. One female founder told Betabeat she had never had a bad experience with Mr. O’Donnell, because she had studiously avoided him. “I heard that there were stories,” she said. “Which is why I never took a meeting with him. But I don’t know what the stories actually were. Just heard about heebie jeebies. Ughhh. I like, won’t walk near him.”

The vagueness of the accusations is perhaps why Mr. O’Donnell, having established his reputation as a notorious asker-outer, has been unable to detect what’s rubbing some female founders the wrong way. No one accused him of molestation, or harassment, or even talking dirty (with one very nerdy exception).

The greatest offense Mr. O’Donnell actually stands accused of seems to be that of casting a very wide net—which raises the question of whether his detractors aren’t perhaps overreacting. “It’s a joke. No one takes it seriously,” one female founder said, of Mr. O’Donnell.