Why We Work Remotely


Fred Perrotta

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

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 self-funded 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. When we did, the supplier was in Long Beach.

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 in the same city, in the same neighborhood 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 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 5 years working remotely with each other and with 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 as shown by companies that outsource the work to India or to the Philippines.

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 and fans for hiring.

Committing to Working Remotely

Lauren joined the team and was incredible. We already knew that we could work remotely. When Lauren joined, we learned the value of hiring people who care as much as we do about our mission.

We learned three lessons at this time.

  1. The previous five years of remote work combined with Lauren joining the team taught us that finding the right cultural fit is more important than finding someone local.
  2. More distributed teams were forming and talking about the practice. From Basecamp to Buffer, we had role models that reinforced our belief that we weren’t completely insane.
  3. Sean Keener, the founder of Bootsnall, turned me on to the Rockefeller Habits which led me to Jim Collins’ work on defining a company’s values. We added "living and working on our own terms" 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 would be harder to do remotely.

We make physical products, not software. Patrick’s work as an industrial designer would be easier if we had an office with a studio where we could prototype ideas and review samples together in person. We don’t, so we have to create a process that works for us and that doesn’t bankrupt us with FedEx shipments between the US and China. We are still figuring this one out.

Hiring Remote Teammates

By making remote work a public, core value, we use it to attract the right people and to filter out the wrong people. As a travel company, remote work is a great perk perfectly in line 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 attracts people who are likely to be a good cultural fit at our company. In reviewing applications and interviewing, we look for signals that someone can be productive outside of an office. I take note of 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. I asked them why, and what makes it work for them.

Why Do You Work Remotely?

Lauren, Concierge

The possibility of working remotely gave me the opportunity to actually have a career. Living with an autoimmune disease, there are days where I have trouble walking, days where I need to take a few hours in the middle of my day to rest from extreme physical fatigue- things that would have been difficult to manage with an office job. Tortuga is not a job for me. It’s a piece of my life — one that I want to build and nurture, and I am so lucky to be able to do that in the environments that make me comfortable. I’ve worked from home, from coffee shops, from a bar beneath my hotel in Iceland, from hospitals.

I like to be alone, but I also love my team. The only real “con” for me is having to wait several months to see everyone together. My list of “pros” could go on forever: flexible schedule, working from where I can, the ability to travel while working — not to mention awesome things like the love and support from team members as we experience changes in our lives. I get to work with some of the best people I know (from a distance).

Angela, Concierge

I work remotely so that I can optimize my time. Taking out the 2.5 hour RT commute every day means I can spend more time working towards my personal goals. It also enables me to work from anywhere. I have a habit of leaving the country for a few months at a time and it’s easier if I don’t have to quit my job every time I do that or worry about money while I’m traveling. It enables me to do this for longer periods of time and more often. I am also a professional freelance dancer. So, wherever that takes me, I don’t have to give up my supporting job.

Patrick, Industrial Designer

I vehemently believe that there are drastic problems with office culture in America. From the assumption that it’s a good idea to be in the office 50–60 hours a week (it’s not for anyone involved) to the idea that work needs should always come before family and personal needs (it shouldn’t). American work life is really screwed up. This doesn’t even take into account the disastrous effects of a long commute which can have detrimental effects on your health and your relationships.

Even the idea that everyone in a company should work the same hours is archaic and flawed at best, discriminatory at worst. The degree to which American office culture revolves around so many concepts that we know to be bad for us as individuals, our companies, and our families is ridiculous.

As a creative, this set up isn’t without its downfalls. I love the serendipity that can come from other members of the team looking at a problem or a design concept with fresh eyes. We all think differently and, often, our best thoughts don’t come in meetings or when we’re “called on.” They come when we’re comfortable, relaxed and thinking about a problem tangentially. It’s hard to replicate that in a remote team, but we’re working on it.

Trust is very important. Remote work does not work unless every member of the team trusts each of their teammates to work in a way that helps achieve the team’s common goals. Working remotely with a small, flexible team like Tortuga allows us to learn what works for the company, the team, and as individuals, while eliminating all of the stupid things that are so common in American work culture.

Jeremy, Co-Founder

I work remotely because I have too much to accomplish to waste time trying to seem busy in an office. I also like to eliminate all the meetings and interactions that I don’t want to have.

I’m a very social person, so sometimes I miss being around people in an office. However, it’s easy enough for me to plan to see people when I want. The benefit of added productivity is well worth it for me.

Taylor, Marketing Manager

I work remotely because I believe in the philosophy behind the movement. I disagree that feeling free and having a career are mutually exclusive. I disagree that work should feel like a daily grind in order to be meaningful. I disagree with using busy and stressed as badges of honor.
I agree that career and work are a part of life, whatever that looks like for an individual, not the beacon around which we schedule everything else. I agree that technology changes everything, and so we should embrace that change.
I work remotely because I want to support the massive change in the way the world approaches the concept of career. And, of course, because it suits me.

Giulia, Production Assistant

Starting to work remotely was a challenging decision for me. Going to the office everyday and desperately trying to clock in at 9.00 am sharp was ridiculous, but I had to do it to avoid the disappointed glance of my previous employer when I was ten minutes late. I feel that now I have become more efficient as I have deadlines and tasks to accomplish in time; before, I was just going to the office and doing the “homework/assignment” of the day.
I enjoy the awareness that even if I live far away from my teammates, we have a common purpose to achieve: building a successful company and in Tortuga’s case, a distinctive brand.

Jenn, Editor

As an early adopter of the remote working lifestyle, I’ve watched the genre emerge along with the industries dipping their toes into the pool. Having spent 8 years traveling full time with my family, the ability to work from anywhere is key to our lifestyle design. In terms of choosing companies to work with, the first and most important questions center around core values and culture. Pulling together with a team of bright, motivated people who “get it” on the same level and have a vision for changing the world is a delight. Fighting the logistics of a remote team with folks who don’t is… well, not. I wouldn’t even consider partnering with a company on a remote team if there was not core value alignment.
My favorite part of diversified teams is the cultural diversity, daily conversations with participants on several continents, and the adventure of creating products and content that crosses borders at every stage, from development to service. That’s my kind of magic.