How a failed yoga retreat sparked a revolution in borderless work
Two college grads hacked their way into the jungle and accidentally created the blueprint for digital nomadism.
Hej! I’m . I’m republishing my book, Global Natives, here on Substack—one chapter each week, for free. I originally wrote the book in 2020 and 2021 during lockdown, and it explores the past, present, and potential of borderless work and the digital nomad movement.
This week, we pick up where last week’s post left off: Bali, 2015, where I travelled to report for The Guardian on one of the early nomad scene’s most influential startups: Hacker Paradise.1 Hope you enjoy reading 😊
Sunlight spilled through the slats, a mix of laptops, flip-flops, and smoothie bowls scattered across low tables in the bamboo coworking space.
—mid-twenties, barefoot, moving at twice the speed of everyone else—waved me over. I’d only traded a few short emails with him before flying to Bali, but I liked him. 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. In person, he radiated a kind of caffeinated, curious intensity that seemed to immediately explain how Hacker Paradise existed at all.Within minutes we were sunk into beanbags alongside his co-founder,
, and they began to tell me the story behind the strange little community I’d just stepped into.A different kind of post-college plan
Back in the spring of 2014, Casey was finishing his business degree at the University of Pennsylvania and half-heartedly applying for jobs he didn’t really want.
The problem wasn’t opportunity—it was fit. The corporate ladders open to an Ivy League grad felt like the wrong game entirely. More than a job in Silicon Valley, he wanted movement, discovery, escape. He wasn’t looking to reinvent anything. If he could find a way to work from somewhere new, that would be enough.
He considered volunteering on organic farms or trading language classes, gardening, cooking, or petsitting for homestays. He liked the idea of mixing work, learning, and travel, but none of the options were quite right. So he decided to invent his own version—a barter deal where he’d trade web skills for room and board—and sent the same short email to six hotels in Central America.
The yoga retreat that wasn’t
It didn’t take long for one to bite: El Sueno Tropical in Costa Rica’s Puerto Carrillo wanted Casey to help them set up a yoga retreats business.
The barter deal was made and Casey booked his flight. Then, the yoga instructor’s laptop was stolen, the retreat was scrapped, and within days the hotel emailed to say there wasn’t enough work to justify his three-month stay.
Suddenly, the whole plan fell apart. This is often the way on the road, but Casey hadn’t even gone anywhere yet. He wanted more than a quick vacation, so he pitched them a different idea: What if they launched a retreat for coders instead of yogis?
The hotel said yes, and Casey started thinking about how to pull off the retreat he’d promised. He built a landing page and arranged video calls with potential attendees. He also began searching for a business partner, posting about his plans on social media and in online communities.
One of the people who responded was Alexey, an Israeli citizen and fellow University of Pennsylvania alumnus. The idea of taking off to travel appealed to him too, but for different, more complicated reasons.
Since graduating, Alexey had been working as a software engineer in Silicon Valley under an H-1B work visa for highly-skilled migrants. Because of the annual cap on H-1B visas, a lottery is used for selection, which means even qualified applicants may not be chosen. In his case, the lottery rejection meant his US employment had to end, and he faced a forced hiatus from the US job market—it would be at least a year before he could apply again. Casey’s project in Costa Rica seemed like the ideal fit to fill in that time.
Casey and Alexey moved into an apartment together at the Costa Rica hotel in September 2014, having never met in person before. Luckily, they got along well.
Hackers in the jungle
The first iteration of Hacker Paradise was the group of young coders who flew out to join Casey and Alexey in Costa Rica. Fifteen people signed up for the full three months, and another twenty or so came and went. There were speakers and mentors, too, whom Casey and Alexey invited free of charge in exchange for talks and business advice.
It’s easy to see the appeal. Rooms at the Costa Rican hotel cost around $25 a night, or $700 a month. At the time, a hotel room in San Francisco averaged $397 per night2—nearly $12,000 a month—and an apartment rental cost about $3,500.3 In other words, jungle life came at a fraction of the price, with a fraction of the commitment.
By the end of the trip in November 2014, Casey and Alexey had learned how to build a remote work community. Their experiment worked: people were productive, happy, and asking where to go next. If one small group could make it work, why not many more?
That realisation turned an experiment into a playbook. Once people discovered they could work from a laptop in the jungle, they didn’t want to stop. Some stayed on; others returned for future trips. Friends, colleagues, and strangers joined after seeing the photos and blog posts. The idea spread organically, one recommendation at a time.
Casey and Alexey soon broadened their definition of “hacker” from coders to anyone—entrepreneurs, freelancers, creatives—who wanted to “hack” their location while working remotely. There was only one rule: everyone had to have a project. It kept out the tourists and party crowd, and set a tone of focus, collaboration, and shared purpose.
Three border hops later, they were telling me this story in Bali.
Building the remote work playbook
In the months after Costa Rica, Hacker Paradise evolved from an experiment into a fledgling travel company—part coworking hub, part group adventure. Each trip offered the essentials of remote life: a place to live and work, a built-in community, and small practicalities like shared dinners and local SIM cards for mobile data.
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 travellers zig-zagged their way to meeting points independently, organising side trips to see monuments, visit friends, squeeze in business meetings, even schedule dentist appointments in cheaper countries along the way.
It sounds familiar now, but in 2014 this was uncharted territory. Coworking spaces existed only in a handful of major cities, and there was no template for bringing that infrastructure on the road. Hacker Paradise was the first to stitch together work, travel, and community in a single experience.
The “work from anywhere” concept was proving especially popular among the alumni of startup accelerator programs like Y Combinator and Techstars. Venture-backed teams like Buffer and Babelverse were already operating as remote, globally-distributed companies, proving that work no longer needed a fixed headquarters. Others followed their lead, leaving San Francisco or London for places where their money, and energy, stretched further.
Before planning their next trips, Casey and Alexey did reconnaissance. They visited each potential destination in person, checking accommodation, food, and coworking spaces, and timing each stop around the local climate. They thought about everything that could derail a remote worker—patchy WiFi, erratic power, bad air quality—and ruled out anywhere that didn’t pass the test. When they couldn’t find the right setup, they built it themselves, hauling routers, extension cords, and WiFi boosters across borders.
It’s easy to forget how different things were in the mid-2010s. Uber had barely reached most cities. Airbnb was still controversial. Google Maps crashed the moment you lost signal, and Google Translate’s live camera feature didn’t exist yet. Buying a SIM card meant hunting down a kiosk and handing over your passport. It really was the wild west of working abroad.
For people like me already trying to do exactly that—those early Hacker Paradise trips solved real pain points. Reliable internet, a decent chair, and a community that understood why you were opening your laptop in paradise: these were luxuries.
From idea to identity
Listening to Casey and Alexey, I felt a strange recognition.
The hum of fans, the tap of keyboards, the smell of coffee and coconuts—it all felt improbably familiar. I’d been living this way for years without knowing it had a shape or a name.
Here were others doing the same: travelling light, chasing ideas across time zones, building careers from laptops. For the first time, I didn’t have to explain myself. I realised that whatever they were, I was one of them.
“Is there a name for people like you?” I asked.
“Yeah,” Casey said with a shrug. “People call us digital nomads.”
It didn’t sound like much—just a label for a handful of laptop travellers in the tropics. But words have a way of sticking. Within a few years, that offhand answer would define a new, borderless generation’s relationship with work, place, and freedom.
Next week: Will there be a billion nomads by 2035?
Pieter Levels—perhaps the world’s best-known digital nomad—made this prediction back in 2015, around the same time I first met Hacker Paradise in Bali.
In next week’s post, we’ll unpack why the more nomadism succeeds, the harder it becomes to define or count, and assess whether the numbers really could reach a billion within the next 10 years.
Thanks for reading. If you’d like to support the project, consider becoming a paid subscriber or share this post with a friend or community that might enjoy it too.
Until next week,
—LRAZ ✌️
MORE FROM GLOBAL NATIVES:
A decade later, Hacker Paradise lives on as part of Noma Collective, organising group trips all year round and visiting over 43 destinations worldwide. They’ve kindly made a special discount available for my readers: Use the code GLOBALNATIVES for $150 off any of their upcoming trips!
San Francisco hotel room prices in 2015 (San Francisco Business Times)
San Francisco rent prices in 2015 (Curbed)
I travelled with Hacker Paradise back in those days as well :), but I don't think I was on that particular Bali trip. Fond memories of finding others out there doing the same thing and indeed getting that term, digital nomad, to finally describe what I was doing. Hubud was also an amazing pioneer, too bad they closed down (although it must be stated that the new nomads request a lot more than they ever offered, for better and for worse...).
What a lovely story - thanks for sharing!