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Featured on Dec 30, 2010

Charlie O'Donnell

"We wear caps and sleeves in this league, son."


I grew up in Bensonhurst and have never lived outside the 5 boroughs--born in Brooklyn, high school in Manhattan, college in the Bronx, baseball in Queens and grandmother in Staten Island. I used to invest in VC funds for General Motors, until Union Square Ventures pitched me for money. The pitch was so good, I joined them. Entrepreneurs pitched me, and the pitches were so good, I joined one. After going out on my own and starting a company, I'm back on the VC side. I'm fascinated by data, systems, and movie quotes. When I'm not taking pitches from startups or running innovation community events, I'm kayaking out of Brooklyn Bridge Park, biking to work, or playing softball.

You and David Lee Roth both kayak in the Hudson river, are you afraid of getting that river water in your mouth?

Well, I try not to drink mass quantities of it, but the river is the cleanest it has been in 100 years.  There's less commercial traffic and there have been a lot of cleanup efforts up river, which is where a lot of the pollution came from.  Also, I'm invincible.

What’s the deal with Jingle Networks, Yapta, FREEjit, myYearbook, Continuity Control, Save Wave, ZoomIn, Gnip, Smartling, KidZui, Iovation, and TechForward?!  Why didn’t they wear bath-related attire for the holiday card?

Most of those entrepreneurs have physiques that are simply too intimidating--so we used the latest CGI techniques to draw clothing on them.

What’s it like working at First Round Capital compared to your time at Union Square Ventures?  You can read all about the different investment strategies, portfolios, and blogs on the internet, however, it’s obviously much different spending 40+ hours a week with the same people.

When I started at USV, I was 25 and just out working on the buy side.  Nearly six years later, I've got a lot of lessons learned from launching my own startup and 3 years of working in venture.  So, number one is that I'm very different in terms of the value that I feel I can add and how much I understand what it's like to launch a successful company--and yet I still have a ton to learn.  In terms of the two VC firms, their strategies are pretty different.  First Round does 25 new deals a year, while USV does about a quarter of that.  FRC tends to play much earlier--so the day to day of the job means my interactions with other team members are different.  The atmospheres are very different--one offices versus three.  At First Round we have a whole backoffice staff, an in-house General Counsel, three other non-partner investment professionals.  When I was at USV, we were just a handful of people in one office and we could all see each other from our desks.  Despite the environmental differences, I feel exceptionally lucky to have worked at the two best venture capital firms in NYC with some of the most successful professionals.  They're very much alike in terms of their entrepreneur-friendly approaches and dedication to adding a lot of value as investors.  The other thing is that both firms are always on--investment related e-mails seem to come at all hours of the day across our teams.  Neither firm thinks of it as a 9-5 job.

Oftentimes the success of an Internet-based company is not a result of its technological innovation.  In your opinion, are there any companies with hugely successful exits that were built on superficial technology?

Well, I don't think technology is ever superficial--even the simplest app can require a lot of work to keep running fast at scale.  However, there are a number of businesses that don't necessarily rely on technical innovation to make money, sure.  GroupOn was nearly a huge exit just recently and that's nothing that hasn't been built before.

Early Stage Investor