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.

Illustration by Paul Kisselev.

Charlie O’Donnell has long eyelashes, an athletic build and a shiny shaved head: a 32-year-old in his prime working at one of the most highly-respected startup investment firms in New York, First Round Capital. The kayaking enthusiast and devotee of the fitness Bible The 4-Hour Body is known to broadcast his nine-mile cycling commute on Twitter, where he goes by @ceonyc, a reference to his initials.

A power networker, Mr. O’Donnell has made himself a fixture at tech parties in search of the next Mark Zuckerberg, or as it were, the next Margaret. Trouble is, he’s also looking for the next Mrs. O’Donnell.

“For men, if we are single, any single female that we are hanging out with has the potential, at least at first, to be a potential date,” Mr. O’Donnell wrote in 2004 on his popular blog, This Is Going To Be Big. “But for girls, you never really know. You can be doing all of the dating type stuff… showing interest, asking them out, etc… and they’ll seemingly go along with the whole thing, until the point that you’re sitting across from them and you realize, ‘Hey… wait a second… this isn’t a date at all!’”

Business and pleasure often mix in the Silicon Alley startup scene, where investors are known to karaoke with their portfolio companies. By now, everyone knows a pitch and a drink can be one and the same—but what about a pitch and a date? With more women on the tech scene, uncertainty is increasingly common.

“I once scheduled a meeting with someone and it turned out to be a date,” one well-connected female techie told Betabeat. That someone was Mr. O’Donnell. One female founder was “asked out to dinner on the pretense of it being a meeting, but it turned out to be a date” with a local venture capitalist, who followed up with an extended series of flirtatious text messages. That man also turned out to be Mr. O’Donnell. In fact, Mr. O’Donnell’s name came up repeatedly in the course of reporting a more general story about women in tech.

Even so, there are far more nefarious scoundrels on the scene. Betabeat heard some stories of other investors that sounded like fodder for Mad Men. “I’ve even heard of VCs trying to sleep with their potential female investees,” said one female founder who used to live in New York and now lives in the Bay Area. “Pretty sketchy stuff.” One woman who organizes tech events said she was stalked for years by a consultant who stopped only after her brother intervened; one female founder met with a Silicon Valley investor who followed up with an invitation to his hotel room via a midnight text message—“and he was married!”

By contrast, Mr. O’Donnell’s dalliances aren’t perverse—just pervasive. And by most any standard, the energetic VC would seem to be a catch. A Brooklyn boy at heart, he still lives in Bay Ridge near his family. “To my mother’s chagrin, I’m her last hope for local grandchildren,” he told Betabeat in an interview. A product of the Jesuit-run Regis High School on the Upper East Side, he started at the General Motors Pension Fund as an intern in high school and eventually landed a job there. He works hard, plays hard (in addition to kayaking, he runs a pick-up softball game and a dodgeball team), has good taste in restaurants and seems earnest about matters of the heart. “I want to find someone who not only loves me, but lets themselves experience love and doesn’t worry about the chances of things actually working out,” he blogged in 2008.

[Disclosure: While Betabeat was reporting this story, we discovered that an Observer Media employee had briefly dated Mr. O’Donnell. She had no involvement in this article.]

Mr. O’Donnell is exceptionally well-connected in the scene and yet still puts his calendar online so anyone can request some face time. He’s something of an industry gatekeeper—or as he puts it, “more like a concierge.” Mr. O’Donnell, though he says he doesn’t drink, attends a vast number of events; socializing is practically a job requirement. “The reason I get the results that I do is because I’m a part of the scene,” he told Betabeat. “I have a big social network, and that leads to a lot of inbound. I get an early look at a lot of good deals because I am out at the parties.”

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