Perspective and Environment

When I left my job at Lehman five years ago, I left New York City as well. I grew up in Brooklyn, but had never lived more than a couple hundred miles away. I said goodbye to the people and family that I love, and I bought a ticket across the world with little idea as to what I might do, how I might earn a living, or what value I might create in the world. I traveled the continent of Asia and ultimately I received a scholarship to attend the Hong Kong University of Science and Technology as a graduate student.

In 2008, I would’ve told you I was leaving New York for all sorts of reasons. But looking back, I think it was a simple one - I left to renew a basic connection with humanity; one that wasn’t entirely lost, but gradually worn from decades living on the same streets in Brooklyn and one awful year on Wall Street.

Since I returned to NYC four years ago to build my first startup, I’ve been largely sedentary. My occupation - building and investing in young companies – both requires it and justifies it. Professionally, I feel deeply lucky to be doing what I’m doing. But personally, I think I’ve lost some perspective. This doesn’t mean I’m unhappy, in fact quite the contrary. But I’m sure as hell unbalanced, and I often feel bad about that. In fact, if I may speak more broadly, the entire startup community, documented well in Packer’s recent article in the New Yorker, seems to have lost some perspective.

Last week I traveled to Colombia for some time away. It was my first time out of the country in years. By no means was I slumming it, but I had limited access to the Internet and generally tried to stay off the grid. And holy shit, what an incredible reset of mind and perspective. Below are a few thoughts I’ve returned with:

Will I miss out by saying no to these events more often? Possibly. But I also know the best relationships I’ve built have been through actual work, on investments or companies with people that I respect, building friendships that exist outside the walls of VC dinners, discussing technology and our careers and our lives away from ticketed events.

Will I miss the next great entrepreneur by saying no to these events more often? Possibly, but I don’t think so. Because the best entrepreneurs I know have perspective. They’re out there in the real world, living and building their companies. Of course there will be exceptions, more likely so in Silicon Valley I think, but I couldn’t imagine Perry from Kickstarter, Georg from Paper, Nick from Tobe at some angel pitch event - they would have been too busy building their business and interacting with the industries that will help them get there – the arts, fashion, film, music, publishing, and all the others that make NYC so great. These are the types of people I want to find and invest in, and by the way, they’re a hell of a lot more fun to spend time with.

Last night I had dinner with my closest friend since I was in pre-school. He works in a development office at a school. While we were ordering, literally while the waitress was speaking to us, I had my nose in my iPhone. Alex promptly scolded me, with good cause. And I realized that I’ve been back for less than a week and it’s already gone, that thing called perspective, which often isn’t a far cry from respect. So I’m writing all of this down and sharing it so that I don’t forget it. Really, I’m calling myself out, even if it just amounts to a public record and nothing more.


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