He Wants to Shake Your Hand: First Round Capital’s Man in Manhattan

Charlie O’Donnell has the figure of a Ninja Turtle, a shiny head and long, dark lashes. At 31 years old,

Charlie O’Donnell has the figure of a Ninja Turtle, a shiny head and long, dark lashes. At 31 years old, he is the finest networker in the city’s tech scene and the “entrepreneur-in-residence” at the New York office of First Round Capital, a Philadelphia-based venture firm that takes pride in placing its bets on embryonic, “pre-revenue” start-ups.

Last week, it was reported that First Round Capital had raised a $126 million fund, part of which will end up in the pockets of entrepreneurs in New York. Just which ones receive the funding depends on decisions to be made by Mr. O’Donnell and the rest of First Round’s New York squad.

Two facts that Mr. O’Donnell told The Observer about himself in an interview Tuesday that are very misleading: He has a barbed-wire tattoo high up on his forearm, and when he’s working out he listens to Rammstein, Rob Zombie and Marilyn Manson. Wearing relaxed-fit blue jeans, gym shoes, his Fordham class ring on one hand and his grandfather’s 50th wedding-anniversary ring on the other, Mr. O’Donnell reported these surprising facts somewhat sheepishly. Of his workout music, he explained, “I don’t really get angry–nothing really bothers me–so I need something pretty extreme to get the juices going.”

Mr. O’Donnell is very polite and very positive. He went to the Jesuit-run Regis High School on the Upper East Side; he is a kayaking enthusiast; and he likes playing team sports. He doesn’t drink. Lately he has been biking to work from his home in Bay Ridge while listening to the Inception soundtrack. Growing up in Bensonhurst, he took pride in being the rare breed of Brooklyn kid who hung out on stoops listening to Pink Floyd and playing chess.

He has written on his blog that New York is home to lots of people who do more talking than working–people who are always “tagging themselves on the 8,000 pictures they took of themselves during social media drinkups and tweetups.” Mr. O’Donnell’s advice to his readers: Avoid those people at all costs. Instead, “strike to seek out those who are actually changing the world.”

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Sitting in a conference room in First Round’s fifth floor office at 200 Park Avenue South, Mr. O’Donnell said he thinks that most people in the New York tech world are not good enough at networking. Young people today are taught to fear strangers, he said, and it’s crippling them in their careers. “In entrepreneurship and venture, my whole world is strangers,” he said. “My calendar is full of people I haven’t met yet. It’s not natural to a lot of people.”

Like many of the “thought leaders” in the New York tech community, Mr. O’Donnell projects an earnest bearing in a way that may bristle New Yorkers unaccustomed to the conventions of his industry. This earnestness is most plainly evident on his well-trafficked blog, “This Is Going to Be BIG!,” which he has updated continuously since 2004, back when he was a recent Fordham grad working in private equity. At the time, he was planning to apply to graduate school and trying unsuccessfully to find a publisher for a book he’d written for college freshmen called Start Strong, Graduate Great, on how to have a career going by graduation.

When Fred Wilson of Union Square Ventures came to the General Motors Pension Fund, where Mr. O’Donnell had started as a high-school intern, and asked them to invest in their first fund, GM passed. Mr. O’Donnell, however, was intrigued, retaining a relationship with Union Square and pretty soon was invited to work there.

That was the winter of 2005; at the time, there was not much of a New York tech community to speak of. To rectify this, Mr. O’Donnell in early 2006 cofounded NextNY, a listserv and event series geared toward jump-starting a social scene populated by local entrepreneurs, developers and all kinds of other “up and comers” in digital media and technology.

After less than two years at Union Square, Mr. O’Donnell left to found a Web start-up–in keeping with Mr. O’Donnell’s lifelong passion, it was a career-guidance service. Even as the company ran out of money, its CEO rose in prominence as a super-connected organizer of industry events and a prolific blogger.

He maintains such an active social schedule that when you ask him to coffee, he directs you to a Web page where you can look through his calendar yourself and see where he has open slots in his schedule. There is a disclaimer: “Please don’t be offended if I a) decline because I respect your time and don’t see First Round getting to a ‘yes’ on your business or b) opt for a call instead of in person.”

For a tech investor in New York today, Mr. O’Donnell said, the pace is just part of the job.

“There was a time in New York when you could sit back a little more,” he said. “If you were a tech investor, there was just a limited number of sources. You could hang out at Bell Labs and spin out some technology or stay in touch with the MIT folks and see everything coming out of there. Now start-ups just fall out of the sky here.”

In other words, you need to really hustle to see the good stuff. “You have to turn over every rock.” Mr. O’Donnell said. “Be there first. Which is hard– I mean, it’s very competitive.”

When The Observer said goodbye and started for the front door, Mr. O’Donnell poked his head into the lobby. Waiting there was a mild-mannered young man with very uncomfortable-looking brown shoes. Mr. O’Donnell welcomed him in.


He Wants to Shake Your Hand: First Round Capital’s Man in Manhattan