I have read in other interviews you have done that you’ve never liked the question, “where are you from?” But I am curious to see how you might begin to answer that question and I also wonder what brought you to Rome?

I usually give two answers to this question: the short one and the long one. The short one is: I was born in Sri Lanka, raised in Italy, and I'm Canadian. The long one is, you don't want to know. And then I start listing out a whole bunch of different countries, the majority of which I lived in only briefly. I have also moved back and forth several times. For example, when I was younger, I moved to Canada, then we moved back to Italy, then to the UK and then back to Italy. Those kinds of changes are very difficult to understand if you have not had that lifestyle. So those are my two typical answers. As you can tell, I struggle every time someone asks me this question.

What brought me to Rome was my father getting a job offer with the World Food Programme (UN) when I was less than 6 months old.

I think that answer will resonate with many of our students who have had a similar experience of growing up around the world. Could you describe what it was like for you at St. Stephen's and what some of your fondest memories are of your time at the school?

St. Stephen's was a foundational time of my life. It's something that I recall regularly and I think about frequently both for the good and the bad, actually. My experience at St. Stephen's was magical. It was magical because this was one space that I would literally go to by 7:15 AM in the morning. I would meet my friend, Carlos and we would take the Metro together. We’d meet around 6:50 and we'd be at St. Stephen's by about 7:15 then I would stay there till eight or nine at night. I would go on the weekends too. So what you can tell is that I loved not just the physical premises but really the experience, which comprised the people and the classes. My fondest memories include the times when the headmaster at the time, Paul Allen, would scold me and several of my friends because we were always strewn on the floor, either in the Cortile or by the lockers, literally lying on the ground, blocking everybody. And we would do this every single day.  After you had spent hours sitting in a chair or throwing a basketball, you'd want to chill, listen to music, relax with friends, things like that so we would just take over whatever space was available and that space was the floor.

What were you usually doing at school until seven or 8:00 PM? Was that for an extracurricular or just to be in the building?

Hanging out. We were always just hanging out. We were playing sports all the time, basketball, calcetto, listening to music, and chatting with friends.

After St. Stephen’s, what came next?

So, I graduated when I was 17, and I mention this, not because it was impressive, but because I was impressively immature. I got into a program in electronic and electrical engineering at the University of Birmingham, which was apparently a prestigious program at the time. I went to the UK, I set myself up and I missed Rome. That's the first thing that I remember, I missed Rome like crazy, more so than my family that actually ended up moving at the same time to India. I missed Rome just for what Rome was and I missed St. Stephen's. What I ended up doing was something a little bit more mischievous.

I tested out my chops as an entrepreneur. I was not very happy with my program. And so, I spent less and less time in the classroom. Instead, I was thinking, okay, why don't I try to do things that will make me a bit of money. Now, a lot of my friends at St. Stephen's know this about me because I used to be a point of mockery for doing these kinds of things.

I started by doing things that I shouldn't have. My first activity was buying a CD burner which was a pretty novel thing in ‘98, and I would buy CDs, burn copies, and sell them for a profit. Now, I should note that I have since tried to absolve myself from this and other things.

I ended up finding other schemes to make money, many of which were not exactly legal. I think it was really important for me to go through this as another formative experience. I say all this openly, publicly because it was a learning moment for me to be able to understand what it meant to live on my own.

I blew all the cash that I had for half a year within the first day by buying a monster stereo that I stuck in my tiny room. And I was just completely disoriented in terms of being on my own at that time.

What's funny is my parents actually offered for me to do a gap year. And I said, absolutely not, I wanted to stay on par with my friends who were going to graduate on X date. I wanted to make sure I didn't fall behind.

What ended up happening was, with the money that I was making, I would spend it all on coming to Rome. You would still see me at St. Stephen's, you would still see me at the Yellow Bar. That year was a bit tough because I just didn't come to terms with the fact that I had left Rome.

I did this back and forth until my father found out for various negative reasons and that was the end of this game where after I had disappointed my university, my parents, and many of my friends. It was time to turn a new leaf and try things in a different way.

So you mentioned that you started in engineering, but you graduated in finance, is that correct?

I switched. I totally failed my first year as an engineer (sorry Mrs. Dostert!). In fact, after two weeks, I remember I was soldering a chip and I realized that was not what I wanted to do and that was one of the reasons I stopped attending the courses. I was flunking everything. It was a complete failure of a year but I was pretty decent with math and I was interested in business. In fact, what I realized was that I didn't want to be building chips, I wanted to be selling them.

So when I realized that, I had to go and study business. I took several months off, I want to say it was my own choice, but it wasn't, it was because I got pulled by my neck, from my parents, for the various mischiefs over that year. Following this, it was time to go back to university so I applied for a finance program in Canada.

And then at that point, you mentioned, that you'd already started entrepreneurial activities. Did you know when you chose finance that it would be because you wanted to be an entrepreneur or did that come later?

​​Well, my first entrepreneurial experience started when I was in grade seven, I was a loan shark. I went to a private school in Canada and they used to have what was called a "tuck shop." It was kind of like the bar in the school where you can buy chocolate bars and what not and I'd be lurking there offering high-interest loans to anybody who didn't have cash.

I could spot the people when they showed up: they looked at a chocolate bar, they didn't have cash on them, and then I would sort of say, hey, do you need a buck? And it worked; it was a great business. In grade seven I made too much money.

That was actually my first taste of entrepreneurship. And since then I've tried to do all sorts of different things. I think I always had a knack for making something out of nothing or something that doesn't make sense and trying to make sense of it. And so that's how I moved into entrepreneurship but I didn't have the courage to do it as a full-time vocation. I decided that I wanted to, you know, I come from a strict Asian background, which means that you know, you have to have a stable career and a degree from an elite institution--and I didn't have that-- and then you need to build a career, get a mortgage, get married, follow a very traditional pathway. It was very difficult - the idea of giving everything up and then trying to set up something on the side as a business and then build it and grow it. The trajectory took me 10 years before I had the courage to actually become or try to become an entrepreneur.

What was the first startup that you launched?

My first startup was called IDAMA (which means property in Sinhalese). It was a property service company. It was actually a digital platform for ordering plumbers, carpenters, and electricians, and it was launched in Asia - in Sri Lanka. It was a really interesting experience because it was a B2C platform that eventually pivoted to become a B2B, which meant that instead of going to households, I went to businesses and this became really interesting because it became much more viable.

We ended up as a business platform that transitioned to be a construction company because those businesses that wanted to pay us to find plumbers and carpenters were largely construction companies that asked us to find a hundred plumbers and a hundred carpenters. And so we moved more and more into construction as a business.

It was sound and we did really well but as a company, I was not very happy or proud of it because it was not a tech company, which was actually what I wanted to launch. So my girlfriend at the time, wife now, and I decided that we wanted to leave Sri Lanka so I sold off the portfolio and we decided to move back to Europe and that was my first startup.

You recently launched a new start-up, Qlik.me, the first programmatic advertising platform for the Influencer community. What attracted you to the influencer advertising space?

Actually, what attracted me was the technology that I was trying to deploy. The company was born out of my first startup, where I was thinking, if I was in a property and I filmed the room, could I recognize what's in there and render everything shoppable from the chairs to the carpet to the vase? And that shopability concept stayed with me all the way through to when I started working with influencers.

The reason I started with influencers is because this is such a hot topic. The influencer space is a great place to be able to launch a startup, especially something in the advertising world. I have stayed in the influencer space because it's broken in so many ways and a true startup, at least according to the classic definition of startups, is you need to solve a problem.

And so, as we stayed in the influencer community, we realized that there were much larger solvable problems. We had to figure out how to embed shopability as a component of what we wanted to do and that's much larger than just focusing only on shopability, which was still a very challenging task as a business. The advertising industry is something I'm completely new to, but it's so vast and there's so much room for innovation. I think that the things we're building and doing are so new that the challenge of making innovation into a business is the thing that keeps me there.

That's fascinating. I think the influencers are just exploding: digital influencers, real influencers, it's providing endless opportunities and companies are now creating their own virtual influencers and renting other people's virtual influencers, it's just constantly expanding…

I mean it's moving towards this whole discussion of NFTs and cryptocurrencies, et cetera. It is evolving so quickly now, you know, influencers have been around for about fifteen years, maybe even longer because it started with blogs and then vlogs but it wasn’t anything like it is now.

You mentioned virtual influencers and that’s true, there are people capturing hundreds of thousands of dollars literally with drawings and these same people have followings of fifty million people. But influencers are only one way of looking at advertising. When you're in the advertising space, what is new and what is innovative is what works. I'll give you an example: the first banner ad that was put into existence had a click-through rate over 40% which means that at least 40% of people would see the ad and click on it. Now the banner ad has like a 0.2% click-through rate, if that, which is an insane difference. That’s just because people hate banner ads but we still use them. What's new and exciting right now are these virtual influencers and NFTs and cryptocurrencies. And we're all following it.

Yes, these are definitely topics my students are interested in and they will only become more relevant, it seems. So I wanted to ask you about your Ted talk. You spoke at TEDx Colombo in 2017 and you talked about the diversity of life experience and how it can provide all these benefits, including enhancing our neuroplasticity. During the talk, you mentioned this one quote, which I hadn't heard before, which was, "if you do, what's easy, your life will be hard." And so I was wondering, for you, how have you found that doing what is hard has made a difference?

My wife is going to hate me for answering this question because I only do what is hard and then I add things to make it harder and add more things to make it distracting and harder.

It's actually more of a way of dealing with things and I connect it to a very, very high risk appetite. Realistically speaking, there's a joy in being able to do something incredibly hard and making it through the impossible.

Even with my startup, in the very beginning, it died many times, but the whole purpose of a startup is that it only dies when you give up. Nothing stops you from working on an idea.

And I think that the quote you mentioned was really helpful for me to be able to verbalize my approach to life. And the reason for it is, simplicity and ease is elegant in many ways but I've also found that I gain a completely different perspective from choosing what's hard. Life is in the nuances.

On the one hand, I also try to do it by observing others and being able to talk to and connect with others and understand their perspectives in life. Going through extremely unique experiences shapes you in a way that is unique in itself. The pathway that you carve out for yourself, as opposed to the pathway that is carved out for you, is always something that has added value to my life, even for its cost to me.

I'm probably the only person you know that has been to jail, been deported and broken several laws (and also gotten away with many things). But it doesn't matter. None of it was about breaking the law. It was more about testing the boundaries that my parents, school, and society imposed on me. The only way to see if those boundaries were real is to go beyond them.

Once you navigate to this new space that few people go to, you get a wonderful understanding of the world around you and yourself. You understand your risk appetite;  your perspective vs. others; a whole new way of doing things; there is a significant safety margin between what is allowed, what is frowned upon, what breaks the law and what simply gets you killed.

After that experience, draw your own boundaries.

What are some of your other passions?

Learning. I voraciously capture information. The funny thing is, I actually ingest a lot of information. Many times people look at me and think that I haven't learned and that's actually because I make a lot of mistakes. I got really into neuroscience about ten or fifteen years ago and I applied a lot of that thinking to improve on my sales skills, for example, something that I hate doing, but it's very useful. I really enjoy connecting with people that do things that I'm either not interested in or don't know anything about. And I mentioned those two things specifically because it's a skill to learn things that you're not interested in.

It's really interesting to hear other people's passions and see how you can connect with them through that passion and take it down that tunnel or that black hole in which you follow their passions. I get excited about other people's passions, beyond my own. I probably won't do woodworking and certain things that other people are super passionate about, but I enjoy seeing and hearing about it. And that's part of my learning as well.

Absolutely. what would you consider to be your greatest achievement thus far?

I don't know, this could be a very psychological question because I always feel as though I haven't accomplished anything yet. I would say, it's going to be my next achievement. I think that my greatest achievement is what's coming.

I've never had that response to this question; that's a unique answer. So what do you enjoy the most about what you're doing now or what you plan to do?

 I think it's the dynamic nature of being an entrepreneur. There are many times in life where you are confronted with a problem and there are resources that can support you and then there are problems that you're presented with in which there are no resources to support you.

And I think the reason that I enjoy it so much is because the right answer doesn't exist and the only way for you to be able to move to the next step is to be able to look backward and see if you've survived if you've thrived if you've pivoted if you've done any of these things.

For me, I enjoy it because you're literally at the cutting edge when you're in the startup world, you're at the cutting edge of whatever you're trying to do because nobody will take your approach.

I enjoy entrepreneurship because it's so difficult. I've called myself "the worst entrepreneur in the world" and I say it because I constantly look back and I think, I should have done that differently. And that's part of the learning process but I enjoy it because there's still more improvement, there's still more learning, and there's still more that you need to do. It's an addiction.

So on the same path of continuous learning, we talked about this question before, I have to ask, do you feel like for you so far, it has been a relatively straight path in achieving the goals you've set out for yourself? Or would you say you've been tested along the way and if so, could you talk about what some of those challenges have been and how you have dealt with them?

The clear and straight answer is no, it has not been a straight path. In life I've taken myself to different corners of the earth, I've touched different industries, been in different places, and that is just from a professional perspective. From a personal perspective, I've also taken myself through, I don't want to say true and extreme poverty, but I took myself to a place where I shouldn't have been because I was testing life and testing the different parameters that I should have perhaps not have been testing at the time.

All of this to say, the path has not been straight, but at the same time, I actually am glad that the path was not straight because I think that life shouldn't be lived that way, not just for myself, for everybody, I think that, as I said in the TEDx talk, diversity of experience is a philosophy. The richness of life that comes from a diversity of experiences does not usually come from a straight path.

This same mindset is what gets me through challenges. Life is going to throw you challenges and the attitude you bring to them is just as important as what the outcome is going to be because you can't always predict the outcome regardless of how much effort, resources, etc you put into it.

So to end our conversation, one question that I ask everyone I talk to is, do you have a piece of advice or an important from your professional experience that you would like to share with this year's graduating class if you could speak to them directly, what would you say?

A few things.

Number one, be a good person and surround yourself with good people. You will encounter thousands in your lifetime, if not more, and who you surround yourself with, who you remain in touch with, all of those friendships and relationships that you develop over time, they can age like a fine wine or like vinegar so learn to choose which ones are good for you and which ones are not.

The second one is also about people which is: network. Meet as many people as you can and be memorable to them such that you are able to pick up the phone. It's not just for myself but I say this because all the people that I've seen be successful are those people that are able to very quickly reach those that they need to reach and, if not, it's not within five degrees of separation, but one, and that only happens because you have a very large network. And so I sincerely advocate networking—especially for those that are extremely ambitious—I think that is incredibly important.

The final thing is that it's very easy to stress a great deal and no matter what I say, the graduating class or anybody will stress, regardless. There are exams, there's getting into university, there's doing well in university, there's finding the first job, all these things are not just milestones, but they're also a pathway in life. I think that people, very often, stress too much, for too long, and perhaps because of a misunderstanding of what needs stress and how much.

And so what I would say is to learn to understand that there is a pathway, whether it's straight or not, understand what your pathway is, understand your risk tolerance, and challenge yourself enough times with enough complexity enough richness, but at the same time, don't take yourself to the point where you really are constantly stressing and that applies to school, to family, to life, to work, whatever it is. Stress is something that you can manage. But I've actually seen many people that don't know how to manage it or put themselves in undue levels of stress.

Other than that, smile, enjoy life. In business school, they used to tell us some people are just on the dance floor and they're just sort of living in that moment, you know, and in that moment, they just live without observing themselves. And then there are other people that are able to step back from the dance floor and observe themselves - not living in the moment. And I think it's important to be able to find that calibration, being able to do both things, reflect in life and enjoy it. You know, it's not just about reflection and it's not just about enjoyment.

Absolutely. That reflection piece is so important especially for high school students because it can be easy to get caught up in the IB, college, in the next deadline to meet, and really all of us can find ourselves so easily in situations where we struggle to find the space and time to reflect and think, what does it all mean? What is it all teaching me? What am I getting from this and where do I wanna go? Reflection is key.

Yeah, I did the IB as well and for no particularly good reason, I did the hardest subjects at the time, in higher-level for no good reason and when I was going through that, it was really challenging for me to just do it without a particular goal. And when I look back, I realize the most important thing was the time I spent with my friends. Those friendships are the relationships I still have today and that measures much more in weight than anything I stressed about academically.