Cruise Ships

In July of 2010, I made the decision to leave YouTube. The first thoughts I had were “How am I going to explain this to anyone? How will I tell mom?” To my family, I had the greatest job in the world and the amount of money I was making was unfathomable. They were certainly not wrong in thinking this. Google is absolutely the best place in the world to work and they do pay very well. It certainly was not an easy decision on my part.

About 4 months before, I was backpacking through Europe, stopping off in major cities to present our latest HTML5 work at the local Google offices. It was my first time really exploring a different part of the world. I met fascinating people and experienced many random adventures. I was trapped in Stockholm for 9 days due to the Icelandic ash cloud. I was a successful stowaway on a train from Copenhagen to Hamburg. I had a girlfriend break up with me during a rendezvous in Bruges. Strangely, throughout both the good and the bad, I just kept thinking about how fun it would be tell these stories to my grandkids one day.

The decision to leave Google hit me while on a train through the Swiss Alps headed towards Milan. I had just been mugged the night before in Zurich and lost about $600 USD. It certainly was not a fun experience, but it added yet another crazy story to my list. I sat in the dining car thinking back on everything that had happened. To cheer up, I remember saying to myself “Well, I would never have had these stories if I had played it safe and gone on a cruise.” And that is when a thought occurred to me: Google is a cruise ship.

Large companies are cruise ships. They work very hard to make you comfortable, provide you safety, and satisfy every need you have. There is plenty of free food, great entertainment, massages, yoga, gyms, opportunities to travel, excellent childcare, and plenty of people to connect with, ranging from young to old. You are all moving in the same direction and seeing the same sights along the way. For many people, at different stages of their lives, this is an ideal way to travel.

Google happens to be the best cruise ship in the world, but it is still a cruise ship. What you sacrifice by traveling on a cruise ship is the opportunity to experience the world on your terms. That was the part of backpacking that really appealed to me, even despite some of my misadventures. To me, the negatives were ultimately just part of the risk inherent in defining my own path. Not everyone can tolerate those kinds of risks, for all sorts of reasons. Given my plans for my life, I realized there was only a small window where I could reasonably afford to take big risks. By staying at Google, I became very worried that this window might pass me by. So I left.

I departed with no plan. As I spent months weaving my way through contract work and side projects, I kept looking for paths that spawned random adventures like those that I experienced while backpacking in Europe. A friend suggested I should submit one of my longterm projects to YCombinator. When I did and got accepted, I realized that it was the start of a crazy new adventure with no clear finish line. So I jumped into the unknown and moved to Mountain View where I slept on my friend’s floor for three months. In my mind, the worst thing that could possibly happen was that I would eventually turn up on a beach. The only question was whether it would be with a yacht… or a shopping cart.

Along the way, I discovered that startups are just like backpacking. There is not a lot you can carry with you, you have no real protection, and there are no guarantees your journey will be fruitful. However, by committing to the path you get the opportunity to travel on your own terms. One of the most rewarding parts to me is collecting tons of crazy stories, both good and bad. It is the stories that keep us going when everything goes to hell.

For the right type of person, at the right time in their lives, working on a startup is the best possible way to experience a unique journey that few others have had the chance to or have dared. When I explained to my family and friends that I was starting a company and explained it to them in these terms, it finally made sense to them. I had stepped off a cruise ship and picked up a backpack.

Now, whenever I interview someone who is working at a large company, I begin by asking them “Have you ever been backpacking before?”


Now read this

Eat. Sleep. Exercise. Work.

“Eat. Sleep. Exercise. Work.” I remember Jessica Livingston telling our YCombinator batch this in our first week of the Summer 2011 session. As a first time founder, I was terrified that I was expected to never see my friends or family... Continue →