A Canadian Era of Startups, Defence & Greatness | Harley Finkelstein, Shopify
Be Too Good to Ignore: The President of Shopify on raising globally, reversing Canada’s brain drain, and building world-class companies from Canada.
Shopify President Harley Finkelstein backed ONE9’s defence-focused fund in 2022, when few Canadian investors wanted anything to do with the sector.
At Startupfest in Montreal, after his onstage conversation with former UFC champion Georges St-Pierre, I spoke with Harley about building in Canada. He joined Shopify in 2010, when it was still an early Ottawa startup, and helped build it into Canada’s largest tech company, now worth over US$150B. He is also an active investor in Canadian founders, including as a backer of ONE9’s Special Mission Fund I, Canada’s first security-focused venture capital fund.
We talked about what Canadian founders need to do differently, why they should look beyond local capital, how to reverse Canada's brain drain, and why he believes the country is entering a new era of entrepreneurship.
“Do things. Tell people.”
Recorded at Startupfest in Montreal on July 8, 2026
Canada’s global technology leaders
“I look at ONE9. I look at Dominion. We’re killing it on the defence side of things. If you look at every vertical, every industry vertical, Canada has one of the leaders. Whether it’s Cohere or Wealthsimple or Plusgrade or Super.com or Shopify, in every category of business and entrepreneurship, there unequivocally is a leader that’s based here in Canada. That wasn’t always the case. That is a new phenomenon. The difference, I think, is that thanks to people like you, we’re celebrating those winners. I’m running around telling everyone who will listen to me how amazing Dominion is, or how amazing Ada is, or how amazing Wealthsimple is, because I believe they’re genuinely amazing. That is a new phenomenon here in Canada, where we all celebrate each other’s success.”
Investing in ONE9 while defence was still taboo
“Nobody cared about defence in 2022. But I got a chance to meet Glenn and Mike and the founders, and I was like, these guys are going to build something incredible. They come from industry. Glenn served in the forces. That type of context, plus that type of conviction, I love betting on people like that.”
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ONE9 is Canada’s first national security venture capital firm. It was founded in 2013 by Glenn Cowan, a former JTF 2 (Joint Task Force 2) Squadron Commander in Canada’s special forces. In 2025, ONE9’s venture capital business was acquired by Kensington Capital Partners
Becoming too good to ignore
“We had something on our wall in the early days of Shopify. It said, ‘Do things. Tell people.’ Canadians have always been incredibly good at doing things. You look at Nortel, you look at RIM, you look at these amazing companies. We’re good at building stuff. We have not always been good at the tell-people side of it. We have to be louder about what we’re doing and celebrate each other.
The second thing that I think is super important is that we have to shed the perspective that ‘If I’m living in Ottawa, I have to raise money from an Ottawa VC.’ No. Shopify’s first investors were not Canadian. We thought we were building an amazing product in Ottawa. We looked at who was investing in SaaS at the time. It happened to be Bessemer Venture Partners. We contacted them; they led our Series A and our Series B, and Jeremy Levine from Bessemer is still on our board. That is the lens we have to remove from the Canadian ecosystem: ‘I’m here; I must raise from local people.’ If you’re in Oshawa or Trois-Rivieres or Calgary, and the product or business is ready for funding so you can grow it, go and try to raise from anywhere in the world. Every venture capital firm today is geographically agnostic. Some of it is just getting over ourselves. The more we talk about success, the more we have role models. I’m hoping one day Shopify will be one of those role models. Maybe we are already. It gives other people hope. You cannot become something that you don’t see.”
Canadian founders staying in Canada
We need to do things and tell people; we have to have more role models here. I meet with a group of entrepreneurs, founders of some of the most important private companies here in Canada. The discussion is around how to become large-scale independent companies, whether that’s through an IPO or some other financing model. And they want to stay here. I was born in Canada. I grew up in the U.S. It would have been really easy for me to move back to the U.S. I want to be in Canada.
I think Canada is the best place to live and the best place to raise a family. There’s a joie de vivre. There’s an energy in this country and a culture that is - especially in Montreal, my favourite city in the whole world. I think you can build world-class companies from here.”
Reversing brain drain
“Be too good to ignore. That’s an easy one. Make your company so good that no one wants to go to someone else’s company. Shopify is not competing with another Canadian company for talent. We’re competing with every company in the world. We’re competing with NVIDIA. We’re competing with Apple. We’re competing with OpenAI and Amazon.
Our job is to be so good that people still want to work at Shopify. It’s not to lament that it’s easier somewhere else, or taxes, or bullshit. Be too good to ignore. Not just from an ambition, customer, client, or product perspective, but also as an employer. Make your employer brand so strong that people want to work for you and are willing to move to Canada to work for you. We are creating a reverse brain drain at Shopify, where people are leaving their countries in Europe and the U.S. and moving here. We need more of that.”
Building globally from Canada
“If you can build a global company from Canada and live in Canada, it is the best setup possible. As someone who lived in the U.S., there’s no place I’d rather live.
In 2026, you do not have to be in any one particular location to build your company. You can be anywhere you want. Yes, you have to take trips down to the Valley from time to time to have meetings. You have to go to VivaTech in Europe to meet companies there as well. You can travel around. I still travel 100 nights a year, but I’m doing it while being based here in Canada. I’m very proud of that.”
A new era of Canadian entrepreneurship
“Brand Canada is the best it’s ever been. In my view, we have a prime minister who’s super supportive. The mayor of Montreal just came onstage with me. I meet with her fairly regularly. All she asks is, ‘How can I help?’ I’ve never had that before. No mayor, no politician ever asked me that. Now everyone’s asking, ‘How can I help?’ I think we’re in this new era of Canadian business and entrepreneurship, and I think it’s going to be the most glorious one ever.”
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If you’re building something in Canada, I want to hear about it: contact@ethanmarcoux.com
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