Remote Work Interviews

Owl Labs (OL): You're the founder and CEO of Remote Year. What led you to found your company, and why'd you do it?

Greg Caplan (GC): I started my career in Chicago working in venture capital before starting a company that was eventually sold to Groupon. When I worked at Groupon from 9-to-5, I felt stuck. I wanted to live abroad, experience the world, meet new people, and try new food. I lined up a few consulting gigs I could do from anywhere and prepared to start traveling while I worked. Of course, I love forming a community and doing things with groups of people, so at dinner one night, I asked my best friends if they'd like to work remotely with me and travel the world. They all looked at me like I was crazy!

The next day, I put up a simple website that asked, "Who wants to travel together for a year while working remotely?" I sent the link out to some friends, and it blew up from there. On the first day, over 1,000 people signed up. Over the next few months, more people talked about it and shared it, and journalists started writing about it in the U.S. and abroad. Before I knew it, 50,000 people had signed up. This eventually became Remote Year. It was built out of a personal need because I had the flexibility to travel but was yearning for a community to do it with.

OL: If someone is a digital nomad and they're looking at their options for traveling and working remotely, why would they choose Remote Year instead of buying a plane ticket and heading out on their own?

GC: At its core, Remote Year is a work travel program built to help people be successful while working remotely and traveling the world. It's challenging to plan that without a platform that's built to make that possible. We also handle all of the logistics. We only travel on Saturdays and program our events and activities around the normal 9-to-5 workweek.

Remote Year places a big focus on connectivity to make sure you're connected in your apartment and in your co-working space. We even have a SIM card program so your phone can be connected affordably at your destination. Most importantly, we have a professional community. When you're on our program, you're surrounded by people who will encourage your success rather than detract from that.

The foundation, the community, and the setup help people find success working remotely while having a global travel experience. This is what's unique about Remote Year. We've built a way to support people who are working full-time but want to travel the world while they do. It's different than staying at a hotel or Airbnb and having to figure out travel and work details for yourself. When you're scrambling around trying to get connected, it's hard to be productive. We also have our enterprise solutions team. We have a full-time team whose entire job is to help people have conversations with their employers to get permission to do Remote Year.

We've centralized thousands of different conversations and best practices to help people understand the best way to have that conversation with their boss, navigate the HR aspects, and beyond. It's a challenging conversation, so we developed best practices and have built a program to help people get permission to do our programs. That's been helpful for many people who otherwise wouldn't know how to navigate it.

OL: Do the bulk of your participants come from particular countries or industries?

GC: Early on, I would've guessed our participants would've been concentrated among software engineers — because that's an archetype of remote workers — but it's been far more diverse than that. We've had people from over 45 countries and so many different job types participate in our programs. There are lots of software engineers and designers, but the biggest category of our participants are people in the marketing function.

We also see lots of lawyers, journalists, and writers, as well as folks in people operations, finance, accounting, and sales. Since we're a U.S. company, Americans make up a slight majority of our people, but we've had people from all over the world. They all come from small, medium, and large companies. In fact, we've had folks from both Unilever and Microsoft join Remote Year.

It speaks to the fact that remote work is a mega-trend. It's not just happening in the niches and it's not a fringe benefit anymore. There are studies that say 52% of the U.S. working population is working at least part-time remotely. Technology has made it possible for people to do great work from anywhere, and we're seeing that permeate across the knowledge economy.

OL: What's something people are overlooking when they have those conversations with their manager about going full-time remote?

GC: At this point, most companies are about 90% of the way to making remote work possible already. Most communication happens digitally — they just need the framework for mapping out what communication is going to look like while people are full-time remote. That's a big part of having that conversation with your manager: How am I going to get my work done and how are we going to communicate?

Getting your work done is straightforward — a lot of it is happening in the cloud anyway. How will you communicate? Well, more of that is happening digitally, too. We use a framework to explain to their managers how it will work to help people understand that they're almost there already.

Most teams already operate in a distributed way, and they only need to allow the flexibility to take that distributed way of working to the edge. Working from across the world is what's so cool about Remote Year. We've had thousands of people participate and be successful. Many people get promotions, move up, grow and change, and evolve their careers because, not only are they able to be productive and do great work, but they're more inspired than they've ever been. They're in new places, exposed to new ideas and ways of doing things, and they're getting some of the best work done that they've ever done in their lives.

OL: I want to know more about your fully-distributed team. Where are your team members working from? How big is your team? What are some of the benefits you see with the distributed company lifestyle?

GC: We have about 110 folks on our team globally, and they work all over the world. We have teams on the ground in all 12 of the core cities that we operate in. They're located in Africa, Asia, Europe, and Latin America, and our central team can work from anywhere they want. We have folks all over the world, and we try our best to make that work well.

The key difference between being distributed and being co-located is communication. We're focused on making our communication touchpoints as effective as possible. We use Slack because it's great for asynchronous communication. We use Google Docs as well, which is super collaborative and it allows people to work together in teams.

If you need to be together, it can be challenging to schedule across time zones, but we have a lot of people working at different times. For synchronous communication, we love to use video conferencing — Zoom is a huge part of that. Video is more personal than voice or text, so we try to encourage video when we can. It helps build relationships and trust. We also have a budget for everyone in the company to gather once a year with their respective teams. It's less for working and more for getting to know each other and building trust.

There's a preconceived notion that when you're co-located in an office, you're building that trust. But the reality is, if you're more than two desks away from somebody, it's rare that you interact and engage. Even co-located folks should invest in bringing people out of the office and into more intimate, authentic environments to build deeper connections. That way, when they're working together day-to-day, they have that trust and a connection they can leverage.

OL: What are some ways distributed teams can build bonds and trust, apart from video conferencing, when they can't all be together?

GC: There are all kinds of ways to build culture, even virtually. We have a lot of folks sharing what's going on in their personal and professional lives via Slack and on Zoom. We try to be more intentional about culture exercises, too. Once a month, we have all-hands video meetings where we all come together and celebrate each other and talk about what's happening across the organization.

Once a week, I send out an email newsletter to the entire organization. It's collaborative and I work on it in Google Docs so the whole team can share what's going on. People add pictures of what our remotes are doing every day and what's happening across the world. It's fun to read what's happening every week with our remotes (which is our word for customers) and with our team.

OL: Remote Year recently secured new funding. How are you going to use this investment to expand and grow?

GC: We're going to continue building our four, six, and 12-month programs. We spent the last five years building the foundation to help people be successful working remotely while having a global travel experience, and we're going to continue to invest in building that amazing platform and help people do just that. The other thing we're going to do is launch one or two brand new experiences that we're excited about.

We're in the process of testing out our newest concept called "Destinations," which is a one-month experience. We think it's going to be an incredible option for a somewhat new audience who otherwise couldn't join our programs if they have other commitments or don't want to have as long of an experience. We're excited to make living abroad with an amazing group of people available to a wider audience.

OL: Is there one program that's usually more popular with your remotes? Do people start with the 4-month and then extend if they're having a good time?

GC: It's evenly split between the four and 12-month programs — the 6-month program is newer than the other two. When someone finishes a program, they become alumni and our word for alumni is "citizen." Then you're a citizen in our remote nation, and we have many different experiences and opportunities for citizens to stay engaged.

When someone finishes a Remote Year program, they generally stay engaged. We have a Slack community for people who are extremely active, and anywhere these folks travel across the world, there are people to connect with – from Portland to NYC. I talked to someone who was recently in Ghana and wanted to know if any other citizens were there. It turns out there were four or five others — they all met up and had dinner together!

Another thing we do every month is a "citizens' house" event. We set up in a new location for one month at a time, and it's only available to people who have finished a program. That's an unbelievable opportunity for those folks to come in and hang out with the community in a new location that they haven't been to yet for a shorter period of time.

OL: What's your favorite place you've traveled with Remote Year so far?

GC: I don't think I could answer where the best place is! There are so many great places I've been with Remote Year, and we've operated in about 35 cities across the world. Now, we focus on our 12 core cities — they're the places we've gotten the best feedback about. We have four in Europe and Africa, including Split, Croatia and Valencia, Spain which just has an amazing culture.

Lisbon, Portugal is another hot spot: unbelievable culture, incredible food, great people. Finally, in that region, we have Cape Town, South Africa. Across Asia, we're in Vietnam, Japan, Malaysia, and Thailand — all unbelievable places to be.

Latin America is so close to the U.S. and it's wild to me that more people aren't going there. I've been spending a lot of my time in Mexico City, which is a great place to be. You can't beat Lima — it has some of the best food and ceviche in the world! There are so many places to check out all over the world. I don't know if I could pick a favorite.

OL: What are some of the misconceptions that people have about building remote teams that might be holding them back?

GC: There are two parts. Number one is, "How does remote work, work?" I was recently talking to somebody from Amazon who said for most meetings, everyone just joins via video conference because the campus is so big. It's interesting to think about people commuting across a campus 10 or 15 minutes to go and meet with somebody. You get so much less done. Even in a co-located environment, you're increasingly seeing people operate in a distributed way.

Then, the second question is about trust and accountability. How do you know people are working when they're remote? Managers are trying to understand how it works. How do you measure productivity? How do you make sure people are getting work done? And my big question is: How do you know if people are working hard in a co-located environment?

The challenge of 9-to-5 is that it's built on a relationship mistrust. If I can't see you, I can't see that you're working, and so I don't believe you're working. That encourages the employee to come into the office for as many hours as they can and actively waste as much of that time as possible.

People in co-located office environments are wasting most of the day. They might be productive 20% of the time. People in a remote environment are only able to be judged on their outputs. Over and over again, in study after study, we see that they're more productive, they work more hours, they get more done, and they're more engaged.

It's a misconception that remote workers are lazy or not as productive or don't get as much done. Trust is so important. If you have relationship mistrust and you require your team to be in front of you so you can stare over their shoulders and look at their computer screens, they're also not going to operate with a level of trust. In a remote environment, you have that trust and people are generally getting more work done. They're more productive and are able to succeed.

OL: What do you think is the biggest gap when it comes to making remote work more common across companies?

GC: That's a great question, and we're seeing that remote work is becoming more common, even with the older generation. The tools are in place and people are using them. They're working from home, they're doing work from their cars, they're doing work from bed, but there are some preconceived notions about working from home during the workweek or during working hours that's a little bit more challenging. It's a cultural thing. Some managers are particularly uncomfortable with having their people work remote because, again, they don't have that trust. They don't have an understanding of how that would work.

The way you get over that hurdle and roadblock is for the best people to start demanding remote work. This forces the managers to get comfortable with it and understand it, paving the way for other folks on the team to have that kind of opportunity and flexibility. The technology is there and people are using it. Piece by piece, the roadblocks are getting broken down because the best people are blazing that path.

OL: It's not the fault of managers because so much traditional management training is created assuming the traditional face-to-face, synchronous environment.

GC: If you talk to a sales leader and say, "Hey, have you ever considered your sales team going remote?" they'd look at you like you were crazy and say, "How could you ever do that? No sales team I've ever seen has been successful remotely." Well, of course, they haven't, because the tools haven't been there. They're going off of their historical understanding and there haven't been examples that they're aware of. They're not going to be the pioneer and therefore, they won't make it happen. But, they start to see more and more organizations get comfortable with remote work. The starting point is not to go fully remote but to try it with some top performers who demand it. Once you've seen success with that, then you can let it percolate across the rest of the organization.

OL: What does the future of work look like to you 10 years from now?

GC: The pieces are already in place for work to become more digital. You're seeing productivity move to the cloud and communication is increasingly digital with video, voice, and text. The questions are:

• What happens culturally?
• How do organizations and teams form remote groups?
• How do people come together in a more flexible, interesting, and distributed way?

We're going to see the way people come together and get work done start to evolve. People are still traditionally hired with in-person interviews and most people are full-time employees, co-located in the same city. It's going to be cool to see tools evolve and merge to help people organize in a much more flexible, distributed, real-time way to get projects done.

As teams begin to change, organizations will look a lot different and the way work gets done is going to continue evolving into the future. That's not a clear vision of what that looks like, but the way people come together to work is going to be innovated in new ways.

OL: What makes you most excited about the future of remote work?

GC: We've been talking a lot about remote work and the question is: Now that people have this flexibility, what do they want to do with it? Lots of people want to spend more time with family or live in cool, interesting locations, but increasingly, we're seeing more people want to leverage that flexibility to have life-changing global travel experiences.

When people have these experiences, they grow so much personally and professionally. They build leadership skills, they get comfortable with change and making decisions on the fly, but more importantly, they build and understand innovation and entrepreneurship by seeing how different cultures and perspectives come together in unique and interesting ways.

Finally, they build a global perspective. As companies become international at earlier and earlier stages, having a global understanding and global perspective is increasingly valuable. Almost every company I know of now is doing business across the world. It's difficult to do that if you've never been outside of your own country. Remote Year enables folks to do that in a sustainable way because we help them do it while they're continuing to work and earn money. That's something that has not been attainable for people historically and that I'm incredibly excited about.