Lessons From a New Frontier: Building Startups in the Jungle

Explore what happens when digital nomads trade comfort for adventure and build new businesses in wild, unpredictable places far from home.

Illustration by Abril Carli

This post is part of an essay collection. You can buy the book version on Kindle or subscribe on Substack for new essays.

I had exchanged a few emails with Casey Rosengren, an American in his mid-20s, to organize my trip to Bali, but I hadn’t met him in person or heard his voice. His communication style was concise and efficient—something that stood out in my inbox full of overzealous PRs, startup companies, and tourism boards all vying for press coverage.

That first day, Casey was bouncing around like a kid who’d had too much coffee, though I’d soon learn he never touched the stuff. Casey grabbed Alexey Komissarouk, his co-founder, and we all sat down on beanbags.

The story of Hacker Paradise begins in the spring of 2014, when graduation was nearing and Casey was hunting for his first post-college job, business degree from the University of Pennsylvania nearly in hand. The problem was, he didn’t really want any of the roles an Ivy League education opened up for him. More than a job in Silicon Valley, where he’d sent in a few applications, he wanted to travel.

So, Casey looked at other options. He considered volunteering with World Wide Opportunities on Organic Farms (WWOOF) or striking a deal through the global barter platform HelpX, which connects travelers with homestays in exchange for language classes, gardening, cooking, farmhand, and animal welfare work.

He liked the concept of mixing work and travel, and especially skill-sharing, but none of the options were quite right. He decided to try organizing his own barter deal instead, and reached out to six hotels in Central America with a proposal: web skills for room and board. It didn’t take long for one to bite.

El Sueno Tropical in Puerto Carrillo, Costa Rica wanted Casey to come and help them set up a yoga retreats business. He would create a website for them and help out with online marketing. The barter deal was agreed, and Casey booked his flight. But when the yoga instructor’s laptop was stolen, the program ended before it had even begun (the details are hazy, but Casey recalls sentiments amounting to, “Fuck Costa Rica, I’m going back to the UK.”)

Suddenly, Casey’s whole plan fell apart. This is often the way on the road, but he hadn’t even gone anywhere yet. The hotel said he could still come for a few days, but they didn’t have enough work to honor the three months they’d previously agreed on.

Casey wanted more than a quick vacation, so he pitched them a different idea: What if they launched a retreat for software developers instead of yogis? The hotel said yes, and Casey started thinking about how to pull off the retreat he’d promised. He built a simple landing page and arranged video interviews with applicants. It quickly became clear he’d need help, so he began searching for a business partner. He posted about his plans on social media and in online communities, inviting anyone who was interested to get in touch.

One of the people who responded was Alexey, an Israeli citizen and UPenn alumnus. The idea of taking off appealed to him too, but for different, more complicated reasons.

Since graduating, Alexey had been working as a software engineer in Silicon Valley. As a non-citizen employee, he was living on an H-1B visa for highly-skilled foreigners. Under this system, workers have to reapply every three years, and visas are allocated by lottery. In practice, a person might meet all the criteria and be great at their job, but still be rejected at random.

This is what happened to Alexey.

He was now obliged to leave the United States for at least a year before he could apply again. He had the option to return to Israel, but figured he’d rather travel, so Casey’s project in Costa Rica seemed like the ideal fit.

The first time Casey and Alexey met in person was when they moved into a two-bedroom apartment together at El Sueno Tropical in September 2014.

Luckily, they got along well.

The first iteration of Hacker Paradise was the group of young coders who flew out to join Casey and Alexey in Costa Rica: 15 people signed up for the full three months, and another 20 or so came and went. The group usually included mentors and speakers, too, who Casey and Alexey invited free of charge in exchange for giving talks and business advice.

It’s easy to understand the appeal for the techies who became Hacker Paradise customers. Rooms and apartments at the Costa Rica hotel cost around $25 per night, or $700 per month. At the time, the price of a San Francisco hotel room averaged $397 per night, equivalent to around $12,000 per month. The median price of an apartment rental in the city was around $3,500 per month—five times higher than the offer in Costa Rica.

In November 2014, as their trip came to an end, Casey and Alexey had taught themselves how to build a remote work community on the road. They figured if one group of people could sustain themselves and work productively for a month or two in the jungle, there must be a lot of others who could afford and benefit from the same experience. That initial commitment—to give it a try for a few weeks—is all Hacker Paradise needed to win repeat customers. Once people tasted the lifestyle, many chose to stay, or returned to the community as it spread to different locations around the world.

Word got around; people referred friends, family and coworkers, and others saw social media posts praising the startup’s trips.

Casey and Alexey broadened their definition of “hacker” from coders to any entrepreneur, freelancer, or remote worker who sought to “hack” their location while working remotely. Three border hops later, they were talking to me in Bali.

In the months since Costa Rica, Hacker Paradise had become a fledgling travel company, balancing the heads-down productivity of a startup office with the novelty of global adventure. The only stringent requirement was that trip participants had a project to work on during their stay. It could be a professional project, side project, or something personal. The rule served to deter tourists and party animals, and encouraged shared values of focus, collaboration, and purpose.

The Hacker Paradise remote work package consisted of accommodation, coworking, and community, plus added extras like group dinners and local SIM cards (useful for WiFi on the go). Flights and ground transport weren’t included, since the target audience didn’t board a plane in one country of origin and arrive in a cluster like tourists. Instead, these travelers zig-zagged their way to meeting points independently, organizing side trips to see monuments, visit friends, have business meetings, and get medical or dental work done in a preferred country.

The “work from anywhere” concept was proving especially popular among the alumni of startup accelerator programs like Y Combinator and Techstars. Venture capital-backed companies like the social media management tool Buffer and the live translation service Babelverse had already been founded by nomads, and operated as remote, globally-distributed companies. While many folks stuck around in San Francisco or London after raising investment, some were heading elsewhere to build their companies—places where their money would stretch further.

Before organizing their next trips, Casey and Alexey made sure to visit each potential destination, scouting out accommodation, food, and coworking spaces across Southeast Asia. They also researched and optimized the timing of visits, adjusting for local climate and air quality at different times of the year. They thought about anything that could inconvenience a remote work traveler, rejected places that didn’t meet the threshold, and went the extra mile by, for example, providing their own routers, portable outlets, and WiFi boosters where necessary. As a remote worker often caught out by these aspects of travel, I could understand the appeal.

As Casey and Alexey shared their story, something clicked for me. I’d stumbled across a group of people I had a lot in common with. We looked at the world through the same lens, and brushed up against the same problems.

“Is there a name for people like you?” I asked.

“Yeah,” Casey said. “People call us digital nomads.”

At that moment, I realized I was one too.

Over the following years, I continued traveling as a digital nomad and wrote extensively about the future of work and global affairs.

I also kept in touch with the Hacker Paradise community and joined their trips to explore other parts of Southeast Asia. Casey Rosengren and I became (and still are) good friends, and he introduced me to many other nomads around the world, many of whom appear in or made contributions to this book. None of us realized it back then, but we were witnessing the birth of a new global subculture of digital nomads.

I started writing Global Natives in the spring of 2020, about five years after first learning about digital nomads on my trip to Bali. It was only when the pandemic hit that I stopped traveling long enough to sit down and think about what I’d learned from my adventures, and consider what I wanted to take forward into the new era of work and travel. I ended up busier than anticipated while I was writing the book: I’ve spoken about digital nomad policy at the UN, I’ve been an expert advisor for governments, and I’ve become known as an activist in the wider digital nomad community. I’ve also joined the Y Combinator alumni company SafetyWing to work on making these ideas a reality through a moonshot project called Plumia, an internet country for digital nomads. Those more recent stories don’t appear in this book, but they’ll certainly appear in the next one.

For now, I just want to give you a sense of where these stories have taken me. Too many books analyze problems without offering solutions, and Global Natives aims to unabashedly buck that trend. These pages set out to reveal possible futures and propose pragmatic ways to get there from where we are today.

In this next part of the book, we’ll go through the basics of who digital nomads are and how they live and work. After that, we’ll examine the technology, culture, and mindset driving the lifestyle. Then, we’ll explore the places, policies, and ideas guiding more people to choose this path, and look at the tools and global infrastructure necessary to realize the potential of remote work and borderless living.

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