I experiment with life and share what I find.

I started working when I was six. Not a lemonade stand. My dad's electronics store in Scarborough, Ontario. I'd stand on a milk crate to see over the counter and ring up customers. By thirteen, I was running my own business out of the school cafeteria, buying candy in bulk and selling it to my classmates. Something about the loop of making and selling felt like a language I already spoke.

At twenty-one, I dropped out of a software engineering degree at the University of Waterloo to start a company. No money, no connections, no backup plan. Over the next fifteen years, I built it into a global advertising technology business operating in over thirty countries. We raised $80 million. I was named EY Entrepreneur of the Year. From the outside, it looked like exactly the kind of success story you're supposed to want.

From the inside, it was more complicated.

Somewhere around year ten, I started meditating. Not because I was spiritual. Because I was desperate. The company was growing, the team was expanding, the problems were multiplying, and I was running on fumes. A friend suggested meditation. I tried it. It worked. Then I started doing something unusual: I brought it into the boardroom. Meditation before investor meetings. Mindfulness sessions with clients. It sounds eccentric. It was. But it changed how I led, how I decided, and how I listened.

That practice cracked something open. The same curiosity I'd always brought to building companies, I started bringing to myself. I ran fifteen experiments on my own life: silence, solitude, radical honesty, selling everything I owned, sleeping on a stranger's floor. Each experiment was a question disguised as an action. I wrote about them in my second book, Unlearning.

Then the pandemic hit. I was in New York, grinding. The world stopped. I went home to my parents in Toronto. For months I sat in the Canadian wilderness asking myself a question I'd been avoiding: Am I happy?

The answer was no.

In August 2021, I moved to Portugal on three days' notice. I packed a carry-on suitcase and flew to Lisbon knowing no one. I hired a CEO to replace me at my company. I stepped away from the identity I'd spent fifteen years constructing. For the first time in my adult life, when someone asked "What do you do?" I answered: "Not much these days."

What followed wasn't a smooth reinvention. It was a relapse. Within a year, I'd hired fifty people in a hundred days, become the visible face of Lisbon's tech scene, dated my way across Europe, 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 absolutely nothing. Different city, same emptiness.

I packed the carry-on 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. 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. The man standing in that sand was not the man who'd been grinding in New York six years earlier. He'd changed. Not because he'd figured everything out. Because he'd finally stopped pretending he had.

What I'm Building Now

I live in Lisbon with my partner. I spend my days building things with AI, writing about what I'm learning, and giving it all away. That loop—build, reflect, share—has been the rhythm of my life since I was six years old. The medium keeps changing. The practice stays the same.

Spark Studio is an AI-assisted book writing platform I'm building for authors who want a collaborator, not a replacement. It came from wanting the tool I wished I'd had while writing my own books.

Vibin is both a book and a platform about the democratization of building through AI. The core thesis: now anyone can build. That sentence changes everything about work, creativity, and who gets to participate.

ai.pt is Portugal's AI community. I co-founded it because I believe in building for the city you live in. No funnel, no monetization. Just people gathering to learn and build together.

I've published four books across four genres and I'm writing a fifth. I write a weekly essay at this site and an AI dispatch series called Unprompted. I studied AI at Oxford. I invest in public markets, real estate, and longevity. I was on the board of CAMH. I co-created a daily AI newsletter that reached over a million readers.

All of it is in service of one question: what does it mean to live a satisfying life? Not in the self-help sense. In the real sense. How to build with purpose, love honestly, stay curious, and keep experimenting, even when the experiments fail.

At a Glance