A. I was born in Sri Lanka. My mom was a nurse, and my dad worked in the Health Ministry as a civil servant. When I was 6 years old, my dad got a job at the Sri Lankan High Commission in Canada, so we moved there. But after my dad lost his job, he was unemployed for a long time, and there was a lot of drinking and stuff like that. My mom worked nights, and she was a housekeeper and then became a nurse’s aide. We had this 400-square-foot two-bedroom apartment above a laundromat. They had to grind every month to make ends meet.
I worked a lot. My first job was at a Burger King. I then got a job through a government programme to do data entry. They told me there was so much to do that I probably wasn’t going to get it all done in the summer. But I became obsessed with getting it all done. The same thing happened with another job in high school. The manager told me that I probably wouldn’t get it all done, but that if I did, he would take me to McDonald’s and buy me as much as I wanted. I did all the work, we went to McDonald’s, and I ate six Big Macs. He was flabbergasted. I don’t know how I was able to eat six, quite honestly. I think I trained myself from when I worked at Burger King.
I loved gambling, and I loved card games. I would run a little blackjack game at one of the lunch tables. The kids could bet 25 cents to a dollar. I was the house. I was making $40 or $50 each lunch hour, and it was all the money in the world. On the weekends, I would take that money and sneak into the charity casinos with my fake ID. That showed me that I have a passion for risk, and that I really like decision-making under pressure. I still play a lot high-stakes poker.
I’ve found that a lot of successful poker players grew up poor. And I’m convinced that poor people have a risk tolerance that rich people don’t have because poor people fundamentally don’t value money that much because they’re used to not having it. With rich people, when they’re born rich, a lot of their identity is wrapped up in that because of the way society defines your success by the money you have. So they covet money. I’ve never cared about it that much.
In both good and bad ways. The bad part is that I’m argumentative like my father. I find that a lot of really important decisions in business are sometimes made on faulty premises, so I like to challenge people to go back to first principles on their assumptions.The good part is that I am pretty introspective and humble enough to constantly change my mind, like both my father and my mother. Those traits can be really productive together, but if they’re not well balanced, they can be unproductive. So my constant challenge is to surround myself with people who have the nerve to stand up to me and argue.
I was pretty good at managing early on because I learned how to get to know people and how to understand their motivations. I never allowed myself to just take at face value who they are or how they presented themselves. Part of it was also just the general curiosity that I had about people. I didn’t have a lot of friends growing up, and suddenly I had a context to meet interesting people and ask them about their story. You can disarm people just by saying, “Tell me about yourself.”
I got exceptionally lucky, so I have nothing to complain about. But other people would have looked at the money I was leaving on the table, and they would have made a decision to stay. It was an enormous amount, but it just didn’t matter. It’s about going back to first principles. What do I value? I valued my independence, I valued my creativity, and I also valued winning over the long term. I decided to make a big bet on myself.
I look for a couple of threads. One is the combination of ego and humility. Let’s be honest, a lot of C.E.O.s are ego-driven people. But they also have to be humble in some very precise ways around ideas and decisions, and being able to change their mind. That’s an idiosyncratic combination. Another thread is intellectual curiosity. They ask a lot of “why” questions, and they’re comfortable with the ambiguous nature of things that are unknown. The last one is that you want somebody who’s ultra-resilient, because there are just so many trials and tribulations to building a business. One day it can feel like you’re on the top of the world, and the next day it’s all crumbling down. Can you compartmentalize it, put it in context and enjoy it?
You have to put yourself in a position to learn. And when you’re young, you only learn when things aren’t working. The problem is that you’re never told to go to something that’s not working. You’re only ever told to jump on a rocket ship. There’s a point in time for that, but if you want to be really good at your craft, it only comes through knowledge, and knowledge only comes through experience, and experience only comes through failure.
Courtesy New York Times