Why We Work Remotely

I would love to tell you that we had a grand scheme to build a distributed company back in 2009. Before remote work was trendy. Before anyone other than Basecamp was talking about it.

The truth is that our remote company was an accident.

Jeremy and I had the idea for Tortuga in 2009 while on a backpacking trip to Eastern Europe. When we returned to the States and started working on the project, we lived in separate cities. Jeremy was in film school in Los Angeles, and I worked at Google in San Francisco. We were already working remotely even though we didn’t know the terminology yet.

When we needed outside help, like an industrial designer or a web developer, we found freelancers on eLance (now Upwork). As a bootstrapped startup without any sales, price trumped location.

Not knowing much about manufacturing, we searched for a factory willing to give us a chance and to make our crazy idea. We found one in Long Beach, California.

When our first batch of 100 (!) backpacks went into production, I quit my job, moved to LA, and started working as a freelancer to pay the bills. Jeremy and I were then living just three blocks apart, but we still mostly worked remotely. We didn’t have an office to go to. Both of us work well in isolation where we can grind away at a given task.

After my one year lease was up, I moved back to the Bay Area, and we continued working (more) remotely.

Growing a Remote Team

Years later, Tortuga found its footing, and we began to grow the business and the team. By 2014, Jeremy and I had spent five years working remotely with each other and contractors. When the time came to hire Lauren as our first teammate, location was never a factor. We were already comfortable working remotely. Her customer support work could be done from anywhere. All she needed was a laptop and access to email.

Our comfort with working remotely meant that we could focus our search on finding the right person, not a person in the right location. Rather than searching locally in San Francisco, I turned to our past customers for hiring.

Committing to Working Remotely

Jeremy and I already knew that we could work together remotely. Hiring Lauren proved that we could add people to the team and continue to work remotely successfully.

When Lauren joined, we learned that finding the right cultural fit is more important than finding someone local. We began to value teammates who are aligned with our mission, not just ones who live nearby.

Around this time, other remote companies began writing about their experiences. Basecamp and Buffer showed us that remote work was possible and profitable. Seeing other remote companies succeeding gave us "permission" to pursue the same path.

Sean Keener, the founder of a remote company called Airtreks, turned me on to the Rockefeller Habits, which led me to Jim Collins’ work on defining a company’s values. We added "Working Remotely" to our core values, not to be violated even if it became a detriment.

Our commitment to remote work made the choice much easier when we began to hire for roles that are harder to do remotely.

We make physical products, not software. Our industrial designer's would have been easier if we had an office with a studio where we could prototype ideas and review samples together in person. We didn't, so we had to create a process that worked for us and didn’t bankrupt us with FedEx shipments from Vietnam. Developing physical products remotely remains a permanent work in progress.

Hiring Remote Teammates

By making remote work a public, core value, we use it to attract the right people and filter out the wrong people. As a travel company, remote work is a great perk that perfectly aligns with our mission and values.

If you aren’t excited about working remotely, you probably aren’t a good fit at Tortuga. Remote work is great but does have shortcomings. You won’t tolerate the downsides of remote work if you don’t love the upsides.

Every company says they want to hire self-starters, but we have no choice.

The opportunity to work remotely attracts people who are likely to be good cultural fits at our company. In reviewing applications and interviewing, we look for signals that someone can be productive outside of an office. I note previous remote or freelance work or a history of entrepreneurship or intrapreneurship (within a larger company).

Our journey to becoming a distributed team was accidental. Aside from Jeremy and me, everyone else signed up knowing they were joining a distributed team.

Remote Work Post-Pandemic

The pandemic drove more people and companies into remote work. Temporarily and out of necessity.

Unfortunately, those people experienced a terrible version of remote work. They were forced to work from home without any time to prepare a home office or to coordinate schedules with their family or roommates. They were experiencing working from home, often for the first time, under stressful conditions.

Companies sent everyone home and started working remotely over Zoom without any plan or future commitment to remote work. They kept all of the worst parts of the office, like constant meetings and rigid schedules, both of which are made worse by being done remotely.

Rather than teaching people how to swim (work remotely) in the shallow end, the newly remote companies threw them into the deep end without training or a life jacket.

As a remote work advocate and co-founder of a remote company, I worry that experiencing a bad version of remote work will turn people off to the idea. I expect that we'll have to rebuild trust in remote work and to show people how a truly remote company operates. A company that is committed to remote work and that has designed all of its systems and processes around the idea. Otherwise, remote work doesn't work.