I experiment with life and share what I find.

The year was 1992. I was six years old, standing on a step stool behind the cash register of my parents’ gift store in Ottawa. My sister, a year younger, was beside me. Most kids our age were watching cartoons. We were tapping register keys and sneaking candy bars when nobody was looking.

The store was a playground. By thirteen, I was managing it alone while my parents traveled. I counted the cash, walked it to the bank, called suppliers, negotiated pricing at trade fairs. The stakes were low enough to 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. 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 after a three-year succession plan.

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. Sun coming through the windows. Nothing was broken. Product? Working. Clients? Happy. Team? Focused. Money in the bank. For the first time, every box on my mental checklist was checked.

“I made it,” I said to myself. I waited to feel something. I didn’t.

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. Two years without buying anything. Sleeping on strangers’ floors. Silent retreats alone in my apartment. Selling everything I owned. 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. The inner work and the outer work ran in parallel, never in sequence. 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.

Then 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. And for the first time in my adult life, when someone asked what I do, I didn’t have an answer.

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.