When you were 17, what did you want to be?
I wanted to be a professional soccer player. I was one of those kids who played every sport. I didn't grow until maybe the beginning of high school, so I was really small but really fast. So I played every single sport up through middle school, and in high school it switched and the focus was all on soccer.
I was also really, really obsessed with computers. Growing up, I was always tinkering with things, putting mod shifts in my Xbox and PlayStation, opening up my Christmas presents to solder wires to the motherboard. I built all the computers in our house. I don't remember exactly how I got into it, but I just knew I liked electronics. I remember we had a really old Mac, and I would just tinker with it. I probably got it from movies too, watching sci-fi nerdy movies as a kid.
How did you decide to attend UC Santa Barbara?
First I went to UC Irvine, and then I transferred to UC Santa Barbara. I was recruited by a lot of schools [for soccer]. I remember getting a letter from Harvard, and I wasn't interested at all. I don't think I even replied. Their soccer team is Division 2, and I thought, "No, I'm better than that." Thinking back now, I could have used soccer to get a degree from Harvard! But at the time, soccer was my focus. I wanted to go to the best school to play soccer, and that was it. And Irvine is a great school.
I decided on Irvine pretty early on, maybe even beginning of junior year. I was young. I was also a little bit afraid, because what if I pass up on something and then nothing's available, and then I’m screwed? Looking back, I think I should have waited, but at the time they were very, very interested. My parents said, "When you commit, you commit." So I did, and I went there.
I decided to transfer during my sophomore year because I didn't want to play at Irvine anymore. The coach, politics, all of that type of stuff, blah, blah, blah. Things were changing there, and I wasn't happy anymore. I had friends in Santa Barbara, and I was visiting a lot, and they have a great soccer team. I didn't actually end up playing there though. I was talking with the coach and the team, and then the idea came up to study abroad. So I decided to study in Barcelona for six months.
Studying abroad meant that I would have had to sit out for a year to play soccer for Santa Barbara, and it would have put me into a fifth year of college. The club team there was really, really good, and they were all ex-D1 players, but it was much more relaxed. We even won a national championship with the club team. It was a perfect mix. I finally found a great balance of being able to enjoy myself but also have a serious soccer thing, and I got to study abroad too so it was perfect.
How did you choose your major?
I started out undeclared until I went to Santa Barbara, and then I majored in communication because I wanted to be a talent agent at that time. If I had to guess where it came from, it's probably from Entourage. I never got that far down that path to know exactly what kind of agent - some kind of TV-movie talent agent probably.
I had an internship at a talent agency in Beverly Hills right when I came back from Barcelona. It was exactly what I expected. I liked the fact that you could make something from nothing there, just wheeling and dealing. And I liked that there wasn't a defined role. I mean, it was a lot of photocopies, a lot of printing resumes, a lot of script reading, a lot of going to pick up FIJI water and delivering it to whomever, dropping off dry cleaning for people, picking out specific jelly beans from a whole king-sized bag because the client's kid only liked the red ones. But all my roommates and friends, they were accounting and finance majors and they had internships at Deloitte, and that seemed too cookie-cutter for me.
So there's communications and communication; communications is more like specific tracks for public relations and marketing and advertising, and it's very applicable to specific jobs, which honestly might have been better for me. Whereas communication is really the study of different theories of communication. It was more learning how to put together a research project, which was really hard and interesting. I took one class in TV broadcasting where we applied these different theories to TV production. And I was a research assistant for a graduate student who was doing a two-year study on NAFTA and different unions in Hollywood, and the different strikes like the writers’ strike. That was cool.
How did you get from college to where you are now?
When I graduated, I had some job offers with big talent agencies in LA, and I was going to go to one of those. But I had fallen in love with Spain when I studied there, and I had always told myself I should figure out how I could get back there. All of a sudden, I was researching jobs there to see if it was possible. I stumbled across the whole teaching English thing, and I thought maybe that was a way I could get back there and then find something more permanent that I was really interested in. I thought if I could move there and make a living and make connections, something good would happen. So I went home for a week, and then I was on a plane to Madrid.
I got there in January, it was snowing, it was freezing cold, I hated it. I didn't know anyone, and all my friends were starting their jobs, and I remember thinking, "Should I just start working?" But I thought, “I may never get this opportunity again, and I'm 21, and I'm just going to do it; if I hate it, I'll come back.” I ended up living there for three years.
I taught English for the first year or so, but I didn't really like it. I liked the little kids, but I didn't like the lesson planning part. Having to plan lessons and live with strange people and be in this foreign country…it was a lot at once. I ended up doing what I’d hoped I would do and met new people. I ended up working for an apartment rental agency that specialized in vacation rentals (this was just before Airbnb came out).
I did a lot of different things for them. I helped with some of the marketing stuff, but mostly I was the check-in guy. I drove around on my scooter all day, checking people into their apartments. It was one of the hardest jobs I've ever had. It was just nonstop. I had an emergency phone that I had to keep on me, and it would ring all night. I would have anxiety if I turned it off. It was a lot of running around town, navigating Madrid on a scooter. Traffic was insane. I'm still really close with the people I worked with. My manager is actually one of my best friends. That job lasted about 12 months.
Then, through one of the connections I had, I got a job working on this marketing project at an investment bank. It was an M&A firm that wanted to build this private portal that could connect M&A advisors from around the world to share their merger mandates or acquisition mandates. It was me and one other girl and a team of four guys who were web developers, all Spanish. We had to create this platform and get people on it and design it. It was an investment bank, so I had to wear a suit every single day. I transitioned from being in shorts and flip-flops driving around on a scooter all day, to wearing a suit and tie. I felt so cool doing that.
So that felt great, being in Europe, this is my life. My Spanish got really, really good. But I hit a point where I realized I really needed to start a career. In Spain, that was the peak of their [economic] crisis, and all these people were leaving Spain to get jobs elsewhere with better pay and better opportunities. I used every year as a marker, like, "Okay, where am I at?" I almost stayed another year, but I just hit a point where I was ready to be back with my family and my friends and start a career. I always felt like I could come back to Spain at a later point, but I didn't want to just keep bouncing around. So I decided to go back.
I went back to California, and started applying for jobs. I almost took a job at Airbnb. It was so young at the time. Then I ended up taking a job at Yelp, selling advertising packages to businesses. I focused a lot on dentists and doctors, and I did really well. I ended up working there for four years. I started in San Francisco, and I was in three different offices through our growth in San Francisco. And then I ended in our New York office. Yelp had a great culture, great people, cool offices, great perks, and a great product. Yelp is amazing. I still use it.
It's weird, no one ever says, "I want a career in sales," but I think no matter what you want to do, sales is so good for everyone. It's really hard, but the fact that I can pick up a phone right now and call anyone and I don't care if I get hung up on. Your face turns red and you're flustered, but then life is all good again. It's hard to learn that, but I think it's applicable to a lot of businesses. What you're doing is learning how to read people and figuring out through a conversation how to get what you want and also provide them with what they want. That's really applicable to everything.
I worked for Yelp in New York for seven months, and then I started We Roam.
I had a friend in town and we met up for drinks. He was traveling a ton, working remotely, and he was telling me about it. I traveled a lot whenever I could take advantage of vacation time. Obviously, after living abroad, I always wanted to be moving. But 15 days vacation is pretty limited. So he was telling me all about this idea of digital nomads.
I remember I woke up early the next morning, probably a little hungover, and it was the first thing in my head. I knew there were a couple programs that were providing travel arrangements and accommodations , so I started doing research. I emailed my parents and said, "Hey, I have this idea. What do you guys think of this?"
Even though I had moved up through the different sales teams at Yelp, I knew I wanted to do something different, and I would have loved to do something on my own rather than just go to another company. But I’d never had an idea that I thought was worth doing. Then I had this idea, and it stuck with me, and it was sticking with me for a reason. I had a trip to Australia planned for two and a half weeks, and I came back in mid-January, and I just thought, "I need a partner.”
I had met Nathan [Yates] when I first moved to New York, and he was an attorney, and we were always talking about different ideas. When I brought it up to him, it kind of stuck with him, as well, and we just did it. I just saw it as an opportunity. After researching it, I thought, "Wow, this is a big deal. This is the way of the future." I didn't want to do something temporary. I wanted to do something that could last. And I saw that this was the way things were progressing. And it was exciting. I've always loved to travel, and this checked off all the boxes I was looking for, for creating something. And it got to a point where I knew if I didn’t try it, I would always regret it. It's funny, if you think about it. People like you, our clients, their ability to work remotely gives me the ability to work remotely.
And maybe it goes back to me being into technology as a kid, building computers from scratch. Once you have it up and running, you're like, "Oh, that was cool. I put that together." So even if it all ends tomorrow, I still think I'm better off now than I was a year and a half ago.
Looking back, what seems clear to you now?
Every single great thing that was started was a risk. So don’t worry so much about the future. Risks never just turn out awfully. Maybe it ends, but it doesn't totally end there. There's always the next thing. That doesn't mean you can make dumb decisions. But it means have reasons for the decisions that you make, and then don't worry about it, just go with it. I feel like this is very common advice, but trust your instincts and go with your gut, because no matter what you do you'll gain valuable experience and it will lead you to your next thing. And life is very, very long. I'm only at the end of my 20s, and it's still very early. There's still a lot to go.