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.


Now read this

Native Money

Native advertising is all the rage these days as an emerging form of startup monetization. If you can marry advertising with content, the thought goes, then the user experience won’t suffer much and the ad is just as (or more) effective.... Continue →