Why I’m traveling while building my startup

I’m writing this post from Gate A1 at San Francisco International Airport. In slightly less than one hour, I’m going to board a China Airlines flight to Shanghai en route to Bangkok, Thailand. It’s a one way ticket. Over the next four months I plan to work out of a suitcase (the one pictured above). Now, I’ve been working on a new startup for a little less than a year, and we’re at a big inflection point in our company. We just hired our first employee, signed up our first customers, and plan to raise our first round of funding in Q1 of next year. So why do I think this is a good time to pack up my bags and become a digital nomad?

Traveling spurs creative thinking

In my experience, the biggest difference between doing a startup and working at a large company is how big of a factor creativity plays into the success of the business. Often, a big company actively discourages creativity because the organizational tolerance for risk is usually quite low. This is one of the reasons startups can disrupt big companies, because they are willing to wade into territory that big companies will not dare to venture.

A small example of this is with my first startup, Fantasy Monster. About a year in, I hit a bit of a mental block. My app had been pretty successful, becoming the #1 paid sports app on the iTunes App Store. But I wasn’t really sure what to do next. To figure it out, I needed a change of scenery, so I booked a one way ticket to Australia. Over the next seven months, I visited 12 countries in 3 continents while working on my startup. I was a digital nomad before it became a thing. The app I built during those seven months eventually became the catalyst for the Yahoo acquisition a few years later. When I got to Yahoo, I found out that they were just planning to build the very technology I had developed two years earlier while traveling. What was considered risky and unconventional had become obvious.

I’ve found there is something about long term travel that sparks the correct neural pathways to encourage risk taking. Studies have shown that changing one’s environment is a great way to boost creative thinking. Simple things such as taking walks, or even working someplace with high ceilings, can boost your brain’s creative thinking. The very fact of packing all of your belongings in a suitcase and booking a one way ticket is risky. Everything you experience while traveling this way is new: the people, places and culture. At this stage in our company, creativity and risk management is extremely important. It could literally mean the difference between life and death for our startup.

Constraints can stimulate creativity

Startups naturally operate under significantly more constraints than big companies. However, studies have shown that constraints are actually very helpful when it comes to creative thinking. There is a blessing and a curse that comes with being a second time founder. I have access to a lot more resources than someone who is doing it for the first time, both financially as well as people. However, it’s easy to be a bit too comfortable and not take as many risks as I should.

Another reason I want to live as a digital nomad for a while is that it puts a lot of constraints on my lifestyle. I only brought as much as I could fit into a suitcase. I don’t have to worry about mowing the lawn or cleaning the house (thanks

!). From past experience, these artificial constraints have given me a lot more focus and creativity.

Building a remote-only culture

The workplace is changing. More and more people are working remotely, and companies have been slow to adapt. In the tech industry, it’s becoming increasingly difficult to hire good talent. To compete effectively, I believe startups should consider adopting a remote-only culture. This will greatly expand the pool of accessible talent and give these startups a competitive lifestyle advantage. A lot of great engineers I know only work remotely, and would not even consider a company that required them to come into the office.

Our first engineering hire is from the Bay Area, my cofounders are in Denver, and I’m working from around the world. As a result, we are forced to adopt processes that are conducive to remote work. For example, our startups are asynchronous and done on Discord. Code reviews, design feedback, etc are all done asynchronously. By building this into our culture at the beginning, we won’t have any jarring changes as we grow.

Welp, gotta go. Flight is taking off and for some reason they still make you switch to airplane mode before takeoff. So apologize if this post feels rushed, because it is 😎.