Serial expat and entrepreneur Kunal Kalro at the Wythe Hotel

Name: Kunal Kalro
Founder: OutTrippin
From: Dubai, UAE to Indian expat parents
Has been an expat in: United States, Chile, Argentina, Australia, India
Key Travel Experiences: Chile, New York
Current location: Brooklyn, New York
Recommended reading: Blinkist

Key takeaway: To me, successful entrepreneurship is about impact. To create maximum impact, you need to solve a real problem — but you have to do that in a profitable way so that investors can invest heavily and make a strong ROI, while people benefit from your service.

Full Interview at Williamsburg’s Wythe Hotel

When Kunal and I met at sunset on the rooftop of the Wythe Hotel in Williamsburg this past April, it had been a year and a half since we saw each other last — and even that was a surprise. I was still living in Chicago then, and my Swarm app told me that Kunal had just landed. Kunal is (stick with me now) my Dubai-born Indian friend who I met in Chile through my Kiwi friend Indi who I met in Argentina while I was globetrotting. In an ever-expanding affirmation of what a small, small world it truly is, Kunal had actually lived in Chicago for two years before moving to Chile, so he was in town visiting old friends. What are the odds.

Fast forward through five years, two startups and countless countries between us, and on this night we are meeting at sunset on the rooftop of Wythe Hotel in Williamsburg — Kunal’s temporary neighborhood. He has settled into Brooklyn for six months for the inspiration he needs think through his next startup venture.

With the bright orange ball dipping behind the magnificent Manhattan skyline, it’s not hard to understand why Kunal feels inspired here. We catch up over drinks, and as sunset turns to candlelight, we get to the heart of the matter.

Postnomadic: Kunal, thanks for agreeing to join the Postnomadic club! But more importantly, and very seriously, where did we first meet?

Kunal Kalro: I was going to ask you the same thing! It wasn’t Argentina, right? It was Chile?

PN: Ok right! I met Indi (Indiana June, Kunal’s OutTrippin’ co-founder) in Buenos Aires, when she interviewed me as a travel blogger for OutTrippin. We became friends and when I got to Chile, she had coincidentally just arrived to partner with you.

KK: That’s right, wow. That was five years ago.

PN: I want to talk about Startup Chile, but let’s go back to the beginning. You’re from Dubai, a child of Indian expats. When did you first live abroad?

KK: I moved to the U.S. at 16 to go to Indiana University.

PN: You started college at 16?

KK: We were on the British system in Dubai, and I was already on the younger side there. When I graduated, I was accepted to Indiana University. I was far away from home (and my very traditional Indian parents). I had a blast. Because I was so young, I stayed for an extra year and got a Masters in Information Systems so that by the time I actually moved to Chicago for my first ‘real’ job, I was actually of legal drinking age.

PN: What was the ‘real’ job?

KK: A consultant at Ernst & Young. I hated it. That first morning, I walked into the building like ‘Hell, yeah,” so excited to start my life in Chicago. That afternoon, I left like, “Hell, no,” knowing that I was going to hate my time there. It was 2008, the start of the financial meltdown, and I stayed on for two years while I figured out my next step. I couldn’t just change careers, because my work visa kept me beholden to a specific company. If I wanted career freedom, I would have to leave the country.

PN: How did you end up in South America?

KK: My parents are Indian and I felt I understood South East Asia well. I grew up in Dubai, so I knew the Middle East. When I moved to the U.S., I didn’t hang out with international students — I hung out with all Americans and totally immersed myself, so I felt that I really understood North America, too. South America was totally different and unknown — so I wanted to go there.

Why expats and entrepreneurs love risk

PN: Can I pause here and explore that with you? Why is that? Most people gravitate toward the safe and familiar. Why do you think you were so open to the unknown?

KK: I think it’s a combination of your experiences and your personality type. You know, I could get into the sociological implications of how growing up in an expat household made me feel a sense of comfort in unfamiliar places — that’s a perspective I used to believe. But, I went to a British school in Dubai filled with fellow expats — but they didn’t end up traveling or living abroad. They gravitated toward the familiar, as you say. So what makes me travel and live abroad like I do? To gravitate toward risk? I don’t know.

PN: What is it about nomads and expats — why don’t we want to take the safe route?

KK: I always knew I wanted to move away from Dubai. I always wanted to explore, and to immerse myself in new cultures. I find it hard to believe that my experiences did not have a role to play in this. I was so impressionable at 16. Suddenly, if you move when you’re young, you’re okay with this idea of picking up and moving.

But I think there is also a ‘Fuck it’ attitude here. While others might say, “What are you gonna do, how you gonna make it happen? How you gonna pay your bills?” People like us say, “Fuck it — I’ll figure it out.”

PN: Sounds like an entrepreneur thing, too.

KK: It really does.

PN: Thanks for indulging me. So you moved to Chile at what, 23 years old? Did you move for Startup Chile?

KK: Yes. After I decided on South America, I signed up for a Spanish class in Chicago. A kid in the class with me told me about Startup Chile. I didn’t just want to go to Chile and mess around. I wanted to do something. To learn something. So, I started considering working for a startup — not starting one myself.

Either way, I applied to Startup Chile with an idea I had, worked up a business plan and got accepted. Suddenly, I had a week to decide whether or not I would go. At first, the decision felt difficult, but it ended up being the easiest decision I’ve ever made.

PN: What made it so easy?

KK: I was giving up this imagined security, friends and a life for this completely unknown entity. But when I called my sister to talk to her about it she made me see that I was 23 — what was the worst that could happen. I had nothing to lose. So, I moved.

Moving abroad from abroad, from Chicago to Chile

PN: You moved to Chile the same way you moved to the United States — with a purpose and a plan. What was it like to be a part of Startup Chile?

KK: I was part of the first real round of Startup Chile. After a pilot round of about 20 people, we were 100 in our cohort. My first startup idea, the one that got in me could officially be called my ‘Worst Idea Ever.’ It was a deals program for sustainable tourism businesses in South America, kind of like Groupon. But it was niche on niche on niche and was never going to work. But I received the $40,000 in funding from Startup Chile and stretched that money out for as long as possible.

PN: What happened to that business?

KK: I traveled around for a couple of months, bootstrapping, running out of money and then I moved to Argentina. I ended up living with Indi (our mutual friend) in an apartment in BA, and we got to ideating on a newer startup idea. I knew I wanted to shut down my first business. I also knew Indi was the best person to start OutTrippin with. She was a blogger, understood bloggers, startups and travel. She was a perfect fit.

PN: What was the elevator pitch for OutTrippin?

KK: The goal of OutTrippin was to give people more authentic travel experiences through blogger-curated trips. Itineraries that they themselves had done or planned, essentially.

PN: That’s how I met Indi. She has contacted me about creating those experiences and we became fast friends. Then you two moved to Chile again, right?

KK: We did. We moved back to Chile, got $40k in funding from a Chilean government entity, and stayed 6 months to make it work. Eventually Indi went back to New Zealand while I stayed and slept on friends’ couches, and we both tried to keep it going even when the original $40,000 ran out.

PN: I remember the day you went to Australia.

KK: You do?

PN: I do — we had lunch plans for that day in Chile. You wrote an email the day before and said that Indi submitted an application to an accelerator in Melbourne, was asked to pitch the next day and your startup was accepted into the program for that very Friday, but only if the whole team was there. From one day to the next, you were in Oz.

KK: That’s pretty much how it happened, yes. I loved Melbourne, and was in and out of Australia for about a year and a half. Our biggest success of what would eventually, technically, become a failure, is that we didn’t need to shut it down at all. We were supporting ourselves. We were in an OK position. But it was a grueling struggle, and one that we were never certain would be able to scale.

Find your Everest

PN: What did you learn from your experience?

KK: So much. I learned how to make deals, how to negotiate with people in incredible positions of power, like the COO of Webjet, a huge Australian online booking company. On a daily basis, what gets you going is about learning. As long as I was learning, that was the destination. If your goal is to arrive somewhere, and it’s not big enough or deep enough, then it’s never enough. And you’re never happy.

That’s why I got my tattoo that says, “The journey is the destination.”

I got my other major lesson tattoos don my body, too. “Find your Everest.”

PN: What does that mean to you?

KK: OutTrippin was not our Everest. We just started climbing. But if you’re going to go to the trouble of climbing, you might as well climb the mountain you really want to climb.

PN: So what’s next? Are you staying in the travel space?

KK: I would never start a travel business again. Experiencing new cultures and traveling the world is something I still feel very passionate about, but it’s not something that I want to monetize.

I’m now focused on working for impact. Even if something is not your passion, you can feel passion around creating real impact on people’s lives. That’s something to build a business around. San Francisco cancerous attitude that is spreading worldwide — photo sharing apps or minor bullshit isn’t changing the world. There is no intent for impact.

We are creating privileged solutions to problems that never existed.

PN: Are you thinking of moving into the non-profit realm then?

KK: I’m not a social entrepreneur. To get the maximum amount of impact, you need investors who can invest a lot of money, so you have to think about profit so they can get their ROI out of this. To create impact, you have to solve a real problem. If you solve a real problem, investors will want to invest.

With travel, even if there is an impact — it’s not measurable. Even if people go abroad and come home and are aware of the problems that other people face — it’s not measurable impact. How is it going to change their next purchase decision and how do you calculate that.

PN: If not travel, then what?

KK: I went to India last year to spend some time, and I learned about problems that are basic and systemic: sugar pills disguised as medicines, unnecessary surgeries prescribed by doctors for money. I’m collecting stories about both of those issues, but I’m not sure I’m going to base myself in India, so I am not going to focus on those problems.

I’m intrigued by genetics and genomics, the idea of nature versus nurture, and understanding your nature so you can nurture yourself better and lead a better life. I’d like to do work that allows people to be equity holders in their own evolution.

I want to follow this idea until I find a place I can make an impact. That’s why I’m here in New York — to do this work.

PN: Well, I’m glad you’re here! Thanks for the chat!