Oh, The Places You Will Go With Hackers

Wanderlust in San Francisco used to mean going anywhere west of Mount Sutro to exotic locales like the Outer Sunset. But a new generation of creative worker, backed by the cloud and increasingly ubiquitous worldwide internet connectivity, is seeking to travel outside of the 7×7 to the wider world of the seven continents.

Two startups, RemoteYear and Hacker Paradise, are taking engineers, designers, and other professionals on a worldwide journey across multiple continents, all the while helping them remain productive on their own work and side projects.

If Silicon Valley is a bubble, these are the startups trying to pop it.

There are certainly many eager to pop it. RemoteYear, which will start its tour this June in Prague, opened its application in December and was quickly inundated with over 25,000 applications for the 100 slots available on the trip. Hacker Paradise, which is currently running a contest for a free year of global co-working for three hackers, has already received 4,000 applications in just the first two days since the raffle launched.

Gross Personal Productivity

One thing that surprised me was how both startups are not targeting a leisure crowd. “This is not a vacation, this is for people who want to travel but want to work on something interesting,” Casey Rosengren, a co-founder of Hacker Paradise, explained. They could travel on their own, but “with us, they get this professional stimulation and are immersed in the tech community.” Greg Caplan, the founder of RemoteYear, echoed that sentiment. “We want people to have a good time and be productive and progress in their career.”

That productive global vision comes from the genesis of these startups. Caplan had always wanted to head abroad, but the “loneliness of traveling around the world is what prevented me from doing it.” He asked a group of friends to join him working from abroad, but many responded that it “doesn’t make sense for me right now.” Rosengren of Hacker Paradise was inspired while traveling Central America to find a new way to travel. “I wanted to be working on my projects,” he explained, “and I wanted to travel but not lose the tech community.”

Two Startups, Two Implementations

The two companies may share a common vision, but their actual implementations differ. RemoteYear is exactly as its name implies: a full-year overseas with a group of 100 people, spread across twelve locations, one per month. This year, the group will travel through Europe, Asia, and South America, with four one-month stops on each continent.

Each person is expected to bring their own remote work to the RemoteYear trip, and a program of fee of $27,000 ($3,000 upfront and $2000 per month) covers all costs and expenses including lodging. That pricing structure was “meant to reflect people’s paychecks,” Caplan explained.

Hacker Paradise, on the other hand, is noticeably leaner in its approach. It has a core group of 10–15 people, and there is no commitment to spend an entire year abroad. That said, while people may only intend to come for a month at a time, “People keep extending their stay with us,” Alexey Komissarouk, the other co-founder of Hacker Paradise, said.

That smaller group may provide a more intimate dynamic, but it has made scaling a challenge. Komissarouk continues, “I really miss SAAS businesses, since you can just throw more servers at the process. A lot of what makes this community special is that the group is so small.”

Both RemoteYear and Hacker Paradise have spent significant time curating their participants. Both startups used Skype to interview every finalist for their programs.

A Diverse Workforce

While these trips may sound like the perfect gap year between college and the workforce, the reality is that the workers attracted to these opportunities are often more experienced. For RemoteYear, the average age of a participant is 30.4 years old. Caplan explained that “people who work at companies in really important roles can convert their roles” to these sorts of remote work options, and said that companies such as Google, Microsoft, and HP have shown a willingness to allow their top talent to become digital nomads.

Caplan argues that the increasing competition for high-quality workers is driving this flexibility. “We have found that companies want to support the employees they value,” he explained. “There is a talent war going on for the top talent. Companies that are ahead of the curve are going to win out in this talent war.”

At Hacker Paradise, Komissarouk said that the organization hosts demo days every week to allow its participants to show off their latest work. “We had an architect who showed us at Thursday Demos his museum in Dubai he was designing.” He notes that “Paradoxically, you can get more stuff done while traveling than when you stay at home.”

Global Logistics

There are some minor logistical problems, such as getting internet connectivity to work in countries like Thailand, where the infrastructure is less developed than in the United States. Komissarouk notes that “DIY networking engineer is one of my most useful but least proud skillsets.”

More seriously, these trips do have some difficult logistics to handle, particularly with visas, which Komissarouk calls the “third-rail” of these programs, and Caplan at RemoteYear describes as a “really delicate issue.” Both programs take advantage of typical short-term tourist visas, since the primary activity of the trips is to tour the countries they visit. Given how experimental these programs are though, they are sailing a bit into uncharted legal waters. Ultimately, program participants are expected to learn and follow the immigration rules of their host countries, and so far there have been no problems.

While the professional goals may remain central to the premise, it is ultimately the experience and friendships that will define the success of these programs. Caplan argues that the rise of the cloud and the sharing economy was critical for the launch of these programs. “15 years ago this would have been impossible,” he said. “This new generation doesn’t want to own things, they want to share things and experience things.”

Komissarouk says that the results so far have been fantastic. “I’m really happy with the people I am surrounded by. People become lifelong friends, hire one another, date one another. We are not facilitating any of this, but this is what happens when you are surrounded by great people.”

With the world becoming increasingly global, RemoteYear and Hacker Paradise are piercing the tech bubble by splitting off part of it and carrying it with them on an around-the-world journey. Given the huge volume of applications, it is clear that digital nomads are going to be an increasingly important component of the global workforce, and perhaps, may even change the way we think of vacations.