Casey Rosengren is a 26-year-old entrepreneur who became a digital nomad by creating retreat programs for other digital nomads. He founded his company back in 2014 and has worked remotely out of ten different countries ever since.

Becoming a digital nomad was not something Casey had planned, so how did it happen?..

It all started with an empty hotel in Costa Rica.

The Digital Nomad Lifestyle Might Find You Where You Least Expect It

During his years as a business school student in Philadelphia, Casey founded a few different startups: a website that sold movie tickets at discounted rates, and an online furniture shop in Tokyo. In both cases, he was in charge of sales, marketing, logistics, and some web development. In order to focus on his startup ideas, Casey decided to put his studies on hold. However, after two years in the highly competitive startup environment, Casey knew he needed a change: “I was just feeling burnt out and decided that before jumping into the next business idea, I wanted to spend some time seeing the world and working on passion projects, before I buckled down to work hard on another 3-5 year project.”

To sustain his travels, he started working as a freelance digital marketer and web developer. On a few occasions, he bartered his marketing skills for free hotel rooms: “Free accommodation in exchange for my services was a good way for me to build my portfolio and keep my travel expenses low. One time I was working with a hotel in Costa Rica to help them fill rooms in the off-season, and I pitched them on bringing a bunch of tech people down to do a ‘retreat’. Since no one was doing anything like this at the time, we moved forward with the idea.”

The same day Casey convinced his friend Alexey to come on board and together they came up with a three month-long retreat package that included accommodation, co-working space, entrepreneurship events, workshops and occasional talks with local techpreneurs – all within the hotel vicinity. For the first round of Hacker Paradise, they managed to find 30 participants by simply spreading the word to their friends and former colleagues in the startup industry.

After seeing how well it was received, the two guys decided to turn it into a proper business. They expanded their target market from purely tech people to designers, entrepreneurs and other creative types outside of the tech industry.

Creating a Great Product Might Be The Best Customer Acquisition Channel For Your Business

Most people are afraid of making mistakes, but Casey attributes a huge part of his success to his early startup failures: “A lot of the mistakes I made in my earlier startups were about me not communicating to customers, or taking too long to get the product into the market. But with that experience, I managed to set up a landing page for Hacker Paradise and start taking applications within a week. It also gave me a network of people to tap into to look for participants, a lot of whom became my very first customers.”

Casey’s company has now grown into a community of more than 400 members from over 30 countries around the world. He has expanded the retreats to dozens of destinations across the globe, such as Vietnam, Indonesia, Estonia, Spain, Japan and many others. 

When it was just him and his co-founder, Casey spent a lot of time doing the small things like creating itineraries, community building, dealing with hotels and getting speakers on board. Fast forward to 4 years later, the company has grown much larger with two more facilitators on the team, which allows Casey to focus on growing the business.

When it comes to acquiring customers for Hacker Paradise, nothing beats word of mouth: “Our main customer engagement and acquisition strategy is all around just having a great product and providing a great experience. We work hard to make sure everyone feels connected and included in the community, and that they learn something or grow professionally in some way that they can take with themselves going forward. If we achieve that, the participants become our best marketing tool by talking about the retreat with all of their friends.”

When I asked Casey how he made sure his retreats provided a great experience to his customers, he said Hacker Paradise stands out because of the strong sense of community participants get to build within the three months they live together. Activities like hackathons, demo nights, skill exchanges, and meet-ups with the members of the local tech scene help his customers enrich their knowledge in a supportive environment.

Separate The Desire For Travel And The Desire to Run a Business

When it comes to work, Casey is a firm believer that things are done better when done together. This is a principle that he instils on both his life and Hacker Paradise. He makes sure that there’s a good balance of work and play in his life as it is essential in the digital nomad lifestyle: “A lot of my best ideas have come from random conversations over lunch with other smart, passionate people. Being surrounded with like-minded people can be super helpful when stuck on a business or tech problem as others might have more experience in that area can help you.

If you’re looking to start your own business and working remotely from anywhere you like, Casey shared some of his most powerful tips:

  • Separate the desire for travel and the desire to run a business. If you just want to travel, save up some money and then go backpack, or get a job teaching English somewhere abroad;
  • Learn a skill like programming where there is high demand and a liquid freelancing market to support your travels;
  • Look for problems in your own life that you’d like to solve – there are opportunities all around if you just pay attention and become mindful of the inefficiencies of daily life.

Interested in Following Casey’s Footsteps?

Check out these online courses to learn more about how to become a location independent entrepreneur, just like Casey:

  1. Entrepreneurship 101;
  2. Leadership, Management & Entrepreneurship;
  3. Growth Hacking in Digital Marketing.

Casey also recommends these 3 books for you to read: Man’s Search for Meaning, Give and Take, and Siddhartha.

To learn more about Casey’s work, join a Hacker Paradise retreat or read his pieces on Medium.