Why I Took My 43 Person Startup To Thailand

I rehearsed the upcoming conversation with my VCs a hundred times. In every single one, I imagined them telling me I was insane.

But they didn’t. When I told them I wanted to bring my entire 43 person company on a retreat to Thailand, they didn’t bat an eye. They were fully supportive.

Back in 2015, we went on a retreat and it was amazing. Bringing people together in a new context helps everyone relax and create new connections. Those connections make everything work better, faster, and more cohesively. This time around, I wanted to go bigger.

The idea started like every other… by asking “what if”?

What if we could have a team bonding experience that was more than after dinner drinks? More than a weekend retreat an hour away from NYC?

What would happen if we brought our team together in a context that’s completely different from what the team is used to?

What if we could be somewhere where people could relax, explore, and see a new way to live?

All of these questions led to a natural conclusion.

What if we went to Thailand?

From NYC To Thailand

We chose Thailand for a few reasons.

First, there’s plenty to do. We could spend some time in enjoying the bustle of the city and some time enjoying the natural beauty of the country in a rural resort.

Second, it was easier for some of our remote team members to get a visa.

And third, Roomi is all about living flexibly and freedom. Thailand is the #1 global destination for digital nomads who worship at the altars of these two ideas.

With just a few weeks notice, our team members around the globe packed their bags and took off for Bangkok.

What’s there to do in Thailand?

Between Chiang Mai and the Sabai Sabai retreat our team: ate questionable street food, hiked mountains, threw back a few local cocktails, and got some serious work done.

In fact, we held our first ever company-wide hackathon. Every team, from engineering, to customer experience, to marketing got involved. They built new campaigns, new features, uncovered new insights, and even designed completely new business ideas. The physical results of the hackathon were huge, but the side effects were even bigger. Almost instantly, our teams developed new levels of empathy, understanding, and connection.

In the day-to-day, it’s easy to get caught up in your own little world and it’s unique challenges. It’s easy to lose sight of what other team members are doing and the challenges they face on a daily basis. When you need something from another team, it’s easy to think “Their job is so easy.” Sometimes we may even see other teams as a roadblock.

During the hackathon, our team members got to see exactly how other teams work. They got up close and personal with the difficulties they face on a daily basis. And they saw how other people create magic in their own corner of the company.

The real benefit of a long distance retreat

Living and working together, going on hikes, spending nights relaxing turned our company into a family. The barriers between teams and between managers and employees dissolved.

As one of our product designers said, “It was really amazing learning about my coworkers in different environments. I felt like I learned more about them over a few days abroad than from sitting next to them for months.”

When your team integrates this way, it makes everything in the company run more smoothly. Collaboration happens at light speed. Team members are no longer profiles within slack. They are people you have a personal relationship with

My favorite part of the trip was Hiking Mt. Wat Thum Muang On, which was way tougher than any of us expected. I also loved seeing how the different cultures within our company emerged. Nothing was more striking than when our team from India began dancing to Bollywood, and teaching their US teammates how to do the same.

Building a startup is not for the faint of heart. Late nights are the norm, not the exception. Self-sacrifice is part of getting a fledgling company off the ground. Sometimes it’s easy to get so lost in the weeds, you forget the reason you’re doing it all for.

At Roomi, we believe everyone should be able to live and work anywhere. By bringing the whole team to Thailand, we got a glimpse of what that vision looks like, if just for 10 days.

This retreat will change the trajectory of Roomi. When you bring people together this way, it’s like adding rocket fuel to your business. I’m excited to see where it takes us.

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