I experiment with life and share what I find.

I first dreamed of being in business at the age of six. My parents had a gift store in Ottawa, and while most kids were watching cartoons, I was behind the cash register tapping keys and sneaking candy bars when nobody was looking. My sister, a year younger, was right there with me. The store wasn’t work. It was a playground.

By thirteen, I was managing the store while my parents traveled. I counted the cash, walked to the bank, called suppliers, negotiated pricing at trade fairs. My parents gave me full autonomy and never second-guessed my choices, even the bad ones. The stakes were low enough to let me learn by doing. That feeling, that business is a form of play, has never left me.

In my final year of software engineering at the University of Waterloo, I stopped going to class. I recruited a few classmates, and we started building prototypes of mobile apps, before most people had heard of a mobile app. We showed a prototype of a magazine on a BlackBerry to the editor of Canadian Business. He liked it. His publisher said yes. We were in business. The company was called Polar Mobile. Six weeks after I graduated, Apple launched the App Store, and we launched the iPhone app for TIME magazine. It was the ninth app ever released on the iPhone.

Over the next fifteen years, I built the company into a global advertising technology business operating in over thirty countries. We raised $80 million, hired hundreds of people, pivoted three times, and served nearly every major media brand in the world. In 2023, I transitioned out of the CEO role as part of a three-year succession plan I’d been working on.

From the outside, it looked like the kind of success story you’re supposed to want. From the inside, it was more complicated.

About seven years in, I was sitting alone in my office on a quiet morning. The sun was coming through the windows. Nothing was broken. The product was working. Clients were happy. The team was focused. We had money in the bank. I went through the mental checklist I always went through, and for the first time, every box was checked.

I’d been climbing the mountain of achievement with the assumption that satisfaction would be waiting at the top. I reached the summit, looked around, and the feelings I was expecting were nowhere to be found.

That was when I turned inward. I stumbled into meditation through a yoga retreat and it cracked something open. The same curiosity I’d always brought to building companies, I started bringing to myself. Over the years, I ran a series of experiments on my own life: two years without buying anything, sleeping on strangers’ floors, selling everything I owned, silent retreats alone in my apartment. Each experiment was a question I couldn’t ask any other way. I started bringing meditation into the office. Before investor meetings. With clients. At board meetings. It became part of how I led. I wrote about the experiments in my second book, Unlearning.

Then the pandemic hit. I was living in New York. The world stopped. I went home to my parents in Toronto. And I sat with a question I’d been avoiding: Am I happy?

The answer was no.

Back at my parents’ house in Toronto, I gave myself space. During a birthday meditation, the clarity came. I knew I wanted to leave North America. Within minutes of opening my eyes, I booked a one-way ticket to Lisbon. My flight left in three days.

I didn’t know a single person. I hired a CEO to replace me. I stepped away from the identity I’d spent fifteen years building. For the first time in my adult life, when someone asked what I do, I didn’t have an answer.

What followed wasn’t the reinvention story I expected. It was a relapse. Within a year, I’d hired fifty people in a hundred days, become the most visible person in Lisbon’s tech scene, and convinced myself I’d conquered a new city. Then one evening I sat at a restaurant where I knew every person at every table, and felt nothing. Different city, same pattern.

I packed a carry-on suitcase again. No destination this time.

That was the real blank slate. Not the arrival in Portugal. The departure from the person I kept rebuilding.

I landed in Sydney. Met someone through a friend. An eleven-hour first date that wasn’t a performance. I went back for a second date, then a third, then I stopped counting. We got married on a beach in Sri Lanka in January 2026.

I live in Lisbon with my wife. I write every week, build things with AI, and keep going deeper into the questions that started all of this. I haven’t arrived anywhere. But I’ve stopped pretending I have.