For some Canadian entrepreneurs, moving to Silicon Valley is a one-way ticket. What made you decide to come back?
At the time, I was dating someone in Toronto – it was a long-distance relationship for many years. When my partners and I sold the company we had started, I asked myself, “Is this relationship going to work, or am going to stay in California?” Today, we’re married and we have a wonderful daughter, so that worked out well. But I had also been observing from a distance what was happening in the Canadian tech sector. I was really feeling inspired because it felt like we were at a moment. There was a cohort of companies that were getting to a size and scale that we hadn’t seen in years, and it wasn’t just one company.
I wanted to be a part of that.
I’m a proud Canadian. I think that Canada is one of the greatest places on the planet. I understood the challenges, but as someone who cares about this place I knew it was the right time to come back and build the business in Canada.
Is there still a big cultural difference between Silicon Valley and Canada’s tech sector, or is that changing now?
It’s changing, but it’s not changing fast enough. I’m worried that Canadians aren’t ambitious enough. One of the coolest things about San Francisco is that you can go out to a bar or a restaurant and everybody there is working in tech. On your left there’s someone who founded a company. On your right there are some people who are working at Google or Facebook, or any of a million other cool startups or scale-ups. They’re talking about changing the world, and they’re naive enough to think that they can succeed.
In Toronto or Vancouver or Montreal, we don’t have the same sorts of conversations about how we in Canada are going to build global-changing companies. And I think we need that. We need more of what I like to call “naive ambition” in this country – people who are crazy enough to think they can succeed, and that the companies they build will propel Canada’s prosperity for years and decades to come.
What advice would you give to younger entrepreneurs?
The main advice is that you need to identify a problem and then find the simplest way to solve it. It all comes down to product-market fit. As you scale up, you must stay close to that problem.
That’s what we’re trying to do at Wealthsimple – innovate, yet stay true to our core selves.
Let me tell you a story that illustrates this point. It’s about the time we won a “Webby Award,” – which is like the Oscars of the internet – as the best financial services website in the world.
I suspect that if some companies were to win a Webby, they would tell their design teams not to change a thing or touch one pixel on their website.
What did we do? The next day we went to our design team and said, “Good job, team! Now, tear it down and start again.”
They did. In fact, they designed it again from scratch. And you know what happened the next year? We won the award again, with a brand new site. That’s the naïve ambition mindset, where there is no such thing as “good enough” because you can always do better. You have more data, more insights, and the only way to keep ahead of the curve is to keep re-inventing yourself.