Travelin’ Man

On June 17th, I left my office, got on the A train, and headed to JFK to grab a flight to SFO. Since that day almost two months ago, I have spent six nights in my home in NYC. And it’s not over yet. Between now and labor day, I think I’ll spend another six nights in my home in NYC.

Between June 17th and Labor Day, I will have been to 14 different locations, visited London three times, San Francisco twice, and taken countless flights and trains.

There are some of you out there for whom this is normal. Certainly sales and business development people, investment bankers, consultants, and others live this kind of work life and it’s normal to them. And there are people like Joi and Esther who live on the road and I have no idea how they do it.

Traveling is not normal for me. Back in the late 90s, I never traveled. The joke was that I’d look at a deal if it was between 34th street and Canal street, between 1st Avenue and 10th Avenue.

I don’t like to travel. I don’t like flying, I don’t like staying in hotels, I don’t like jet lag, I don’t like missing my exercise routine, I don’t like waking up and not knowing where I am. I am a creature of habit and feel like I am at my best when I can lock into a routine.

But gradually over the past couple years, I’ve embraced travel and have come to terms with it. It really started with the work I did personally in the aftermath of the bubble to get a handle on things. I learned to deal with stuff I didn’t want to do, starting with air travel. I still don’t like to fly small planes, but I can get on a commercial jet without any apprehension. I don’t like it when the plane bumps around, but I’ve learned how to chill out and deal with it.

The big-time travel that our family has been doing since our youngest was in second grade (2002) has also been a big part of my about face on traveling. We’ve been all over the world and we’ve had a blast. I want to do more of it, not less. I want to see as much of the world I can see, experience different cultures, languages, tastes, and smells.

And then there’s our business. When we started Union Square Ventures, Brad and I were not focused on location. We wanted to invest in the best web applications and services we could find. But we knew the NYC market cold and had a reputation there. We knew we could win deals and make a name for ourselves quickly in NYC. And that’s what we did.

A couple years ago, we started looking outside of NYC and we’ve now made four investments in San Francisco and are looking to make more. We’ve made one investment in London and are open to making more. You can’t invest in companies if you aren’t willing to spend face time with them.  So that means travel and the more companies we invest in outside of NYC, the more I’ll travel.

Honestly, I am torn about it. I still hate to be away from home. This summer has taken a toll on me. I am out of shape. I’ve hurt my shoulder and it’s not getting better. I’ve lost weight. I have bags under my eyes and people tell me I look tired all the time. I am tired a lot of the time.

But I am also energized. In June, I was a bit burnt out on the web. I wanted to be inspired. This summer has inspired me in a bunch of ways. We’ve closed a bunch of new investments while I’ve been away that are taking us in marginally in some new directions. Our firm runs like a well-oiled machine when I am away. I can focus more on other things. I have met literally hundreds of entrepreneurs in Europe who are bucking the odds and doing it the hard way, staying at home and showing that you don’t need to be in silicon valley to change the world. And last but not least, I’ve got a brand new blog and a new domain.

I’ve also been able to have my family with me for much of this travel, particularly in Europe. As my kids get older and start fending for themselves, I hope the Gotham Gal will do more traveling with me. Travel sucks, but it sucks less when you are with your family.

So I’ve become a traveling man. I guess I’ll have to start really using dopplr.

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