Perspective and Environment

When I left my job at Lehman five years ago, I left New York too. I grew up in Brooklyn, but had never lived more than a couple hundred miles away. I said goodbye to my best friends and my family, 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 throughout Asia and ultimately 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 lost, but worn from decades living in Brooklyn and one awful year on Wall Street after college.

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 - quite the contrary - But I’ve felt unbalanced recently. In fact, the entire startup community, documented 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, and with limited access to the Internet, I generally tried to stay off the grid. 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 the actual work, 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? Perhaps, 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.

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. He scolded me for it, with good cause. And I realized that I’ve been back for less than a week and that thing I had while traveling and off the grid was already gone.


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