The Ben Mulroney Show - A conversation about Canadian tech with Shopify president Harley Finkelstein

Episode Date: July 15, 2025

- Harley Finkelstein, Shopify President If you enjoyed the podcast, tell a friend! For more of the Ben Mulroney Show, subscribe to the podcast! ⁠⁠⁠⁠⁠https://link.chtbl.com/bms⁠⁠⁠���⁠ Also, on youtube -- ⁠⁠⁠⁠⁠https://www.youtube.com/@BenMulroneyShow⁠⁠⁠⁠⁠ Follow Ben on Twitter/X at https://x.com/BenMulroney Insta: @benmulroneyshow Twitter: @benmulroneyshow TikTok: @benmulroneyshow Enjoy Learn more about your ad choices. Visit megaphone.fm/adchoices

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And if you cast your eyes back to 2006, a couple of guys had an idea for a business. And that business became, over the course of almost 20 years, an enterprise in this country that so many of us are so very proud of, Shopify. And it has been helping small business owners take control of their destiny

in a way that they probably didn't know they needed. And it is a massive success on a level we are not used to in this country, if I'm being completely honest. And so I'm very, very glad to have on the show for the first time and hopefully not the last, the president of Shopify, Harley Finkelstein. Harley, welcome.

Oh, he's not here. All right, well, listen, while we try to get him back, I'm gonna tell you a little story. Years ago, I started my own handkerchief company, a pocket square company, and we called it Hank, HNK. And we did this, I think I told this story once before, where we found designs that were in the public domain. We found old wartime posters and pieces of art.

And then what we did is we changed the color palette so that when you wore it as a poof in your pocket, it just looked like a really nice splotch of color. And we tried to go store to store to sell these things. Had Shopify been an option for me at the time, I bet you I could have made a go with Hank. I bet you I could have sold this stuff over the internet. I could have made a ton of money.

And there are millions of businesses around the world that are helped each and every day by Shopify. And I grew up in a house where my dad told us every single day, well, not every day, but it was a belief that he had that was omnipresent in our lives, that small business owners are the lifeblood of the Canadian economy. Harley, are you there?

I'm here, he's here. Hey! Hey, Dan. Great to hear from you. I was just telling the story of a business owner are the lifeblood of the Canadian economy. Harley, are you there? I'm here, he's here. Hey! Hey, Dan. Great to hear from you. I was just telling the story that my dad would tell us

every chance he got that small business was the engine of the Canadian economy. They are the ones that take, entrepreneurs are the ones that take risk. They don't take vacation. They don't have a backup plan. They don't have a plan for, they don't have, they don't have a plan for retirement, except to keep their business going. It is the lifeblood of any economy, and it needs to be

supported. And your business does just that. Yeah, thank you. I've had the great honor and pleasure of being both your dad and certainly know your mom too. And I think like me, they also understand that Canada is Canada because of the small businesses and the entrepreneurs here. And actually you grew up in Montreal as I did, and you may recall the Jean-Town law farmers market. Did you ever know that when you were a kid? Yes, indeed. That's where my family's entrepreneurship journey started.

In 1956, my family came to Canada from Hungary during the revolution. They were Holocaust survivors and they had no choice. They had nothing. They had no money, they had no education. And so their way of surviving in this new country was to set up a little egg stall at the Jean Talin Farmers Market. They called it Le Capitaine. And that egg stall still stands today in Montreal, that farmers market. And that was, you know, we talk a lot about entrepreneurship based on passion, but for most people, most of the time, entrepreneurship was the way they survived.

Yeah, yeah, absolutely. And that's really the reason I wanted to chat with you today, Harley, is that, you know, we've got a new government and I, you know, I'm a big believer in fighting your fight and if your guy loses, you get behind the guy who won and you wish him well, right? So I'm hopeful for the next three, four, five years. I genuinely am.

However, in the past few years, it has felt like there have been headwinds that have been battering the entrepreneur class in this country. And I wonder what your thoughts are about the state and the health of our entrepreneurial class in this country. Yeah, well, look, not only do I pray

at the altar of entrepreneurs, but Shopify is very much the entrepreneurship in Canada, but also we're the entrepreneurship company globally. And what I am seeing is I think there's incredible companies being built right here in Canada. I mean, we see it on Shopify every day, McCash, Rudsak, Midday Squares, these companies that are becoming iconic are built right here. But just to say the thing, I mean, half as many Canadians are launching businesses today as they

were 20 years ago. In fact, there are 100,000 fewer entrepreneurs in Canada right now than in 2003. And when you sort of, when you compare that to the US, I mean, US entrepreneurship right now than in 2003. And when you sort of when you compare that to the US, I mean, US entrepreneurship right now is at record highs, you know, but 36% of Americans that are in the workforce, you know, identify as being self employed. If you look at actually business signups in the US, there's about 500,000 every month in the US. So there's a surge of it. And so I do think though that, you know, it's a good time to kind of remind ourselves that most people work for small businesses. For a lot of people that come to this country for the first time, small business is the way that they

they find their families, they find success for their families, they put food on their table. And part of the reason that I think you and I started talking a couple weeks ago was my rallying cry at Toronto Tech Week just a couple of weeks ago was who's going to build the first trillion dollar market cap company in Canada. And the reason I care about that is not just because of the market cap or what that means for the markets itself, but because I do think though that we have to become more of a founder nation and I think a big part of that is education and incentivization. But a lot of that is going to be inspiration. We need, we need more role models that are going to show the path to start companies here and build, you know, the next Shopify's.

Is it, is it as simple as, you know, because we haven't seen it happen very often in this country, most entrepreneurs don't think it can happen in this country. I think, you know, 10 years ago, almost the day, Toby and I took Shopify public on the New York Stock Exchange and the Toronto Stock Exchange. And as part of that, we did a bit of a road show, we went all over the world and met investors and, you know, talked about the Shopify store, get them to to invest in the IPO. And I remember, you know, not everyone, but probably one in

four of those meetings, one in five, immediately, they would say, Oh, great, you guys are Canadian. Well, the remember, you know, not everyone, but probably one in four of those meetings, one in five, immediately they would say, Oh, great. You guys are Canadian. Well, the last, you know, last time we saw Canadians here was, was rim was Nortel. Yeah. And I mean, to just to be clear, I mean, we stand on the shoulders of giants here in Canada. I mean, my, my mentors, the people that I look up to are, are, are, I think are some of the greatest entrepreneurs on the planet. Most of them are Canadians.

And so I think being compared to a Nortel or a RIM, we don't want that to be our legacy. What we want our legacy to be is that companies get started in Canada, that companies get built in Canada and scaled in Canada, and then we stay in Canada for a very long time. You know, Harley, you and Shopify must have felt the pull to move from Canada elsewhere. Certainly. I mean, 2010, we did our series A our first round of funding. And as we were beginning to meet with venture capitalists all over the world, there was a number of very, you know, top tier one VCs who wanted to invest in Shopify. But there was a condition of moving

to Silicon Valley to be closer to them. Yeah. And we resist that pull. We thought actually building in Canada would be a massive unfair advantage. We would have great access to talent. I mean, I love living here. I grew up, I was born in Canada, grew up in the States. I've been living back in Canada since I went to McGill in 2001. We want to be here.

We love this country. We think it's one of the greatest places on the planet to live. But you can also build from here. And part of what I'm trying to do is, you know, raise the level of ambition. We don't want to be a country of acquiries. We want to be a country of acquirers. We want to acquire more companies and not the reverse. And it's already happening.

I mean, when I look at, you know, things like, you know, some of the energy that I saw at Toronto Tech Week was this idea of us becoming a founder nation. I think at the heart of that though, Ben, which is something that you do so damn well, is I think we have to get better at storytelling. I think, we had this poster on our, on the wall in the early days of Shopify,

which was, do things tell people? I think we do things really well in Canada. We have incredible intellectual property, we have incredible engineering, we have incredible products being built here. I think we actually need to get a little bit better about being allowed about that being more proud about that. So do things tell people I think we nailed the do things. I think it's the tell people part of it that we have to get better at it. I'm trying to encourage more of the founders in Canada to be proud and loud about building these great companies right here in Canada.

Well, listen, Harley, we're going to take a quick break. But when we come back, don't go anywhere, because when we come back, we're going to continue our conversation with the president of Shopify. And if it's all right with you, Harley, I want to take a stroll down memory lane. And I want to go back to those early days of Shopify, when you know, the future wasn't necessarily as certain as it might be today. And maybe there are some lessons that can be gleaned for entrepreneurs today who might be today. And maybe there are some lessons that can be gleaned for entrepreneurs today who might be in the early stages

of building their companies. This is a fascinating conversation with one of the great entrepreneurs in this country. I'm Ben Mulroney. This is The Ben Mulroney Show. Don't go anywhere. We'll be right back. Let's take a look at the roads with 640Toronto Big Trouble Traffic.

You're right. This is The Ben Mulroney show. Mr. Voice, thank you very much. And we are in conversation, continue our conversation with one of the great entrepreneurs in this country, one of the leaders of one of the greatest, if not the greatest company in this country, Harley Finkelstein, the president of Shopify. Harley, thanks so much for sticking around. Of course, thanks for being here. So it's been a heck of a journey for Shopify founded in 2006. Today, it is, I think the second biggest company in the country in terms of market cap. But I wanna go back to the early days, after the founding, when, you know,

you're out there hustling for, when did you join the company? During the company, I started as a merchant was the first merchant the platform around 2006. Really? Oh, so right at the beginning? Yeah, and then I joined about three years later. And in those early years, I have to assume that just like most startups, the leadership team was out there scrambling trying to get investors trying to get some money in so that they could keep

the keep the lights on. That's right. Yeah, I mean, we raised our first round of financing in 2010. And then that's at the company public, but five years later. But yeah, those early days were, I mean, you know, it's difficult not to look back on them with incredible, you know, awe and delight and joy, because they were crazy. They were insanely intense. But for any founders that are listening, you know that there's something magical about those early teams, the wonderful team where you're so driven by mission. And I love those early days. If you look back at those days and you compare them

to say someone who's in a startup today, what are the biggest differences? Because the startup founders that I know say it's harder today to raise money than at any point that they can remember. Investors are more risk averse today, or maybe it's just Canadian investors are risk averse. How do you see it?

Yeah, I mean, I don't agree. I mean, I think if you just look at the sheer amount of angel investors or venture capitalists that are out there with private equity funds that are now doing more early stage deals, there's way more capital available now. There's no question about it. There's also more competition for that capital.

But I mean, it was hard then to raise money. It's hard now to raise money. It's supposed to be hard to raise money because frankly, investors don't wanna part with their capital unless they're investing in companies that they really believe in, that they really believe in, that they really think can sort of 10X their investment. My advice though to early founders

who were kind of going through it is, first of all, we've always been a company that, I think a lot of people look at Shopify as being a Canadian company and we are. However, the way we've always thought about our company is, let's build the best company globally, let's just do it from Canada. And that may seem nuanced.

That may seem a little bit strange to say out loud, but this idea that your total addressable market, what they call your TAM, can absolutely be global today. I mean, that's how business is geographically agnostic. So you can build something from, I was talking to Josh Samer, who lives in Saskatchewan yesterday. He built Skip the Dishes.

I ended up selling this company a couple of years after he built it. But he was telling me in Saskatchewan, after Skip the Dishes became this big thing, and all these sort of early employees made money, they've all started their own companies now. They've created sort of this ecosystem of reciprocity and this flywheel effect. So I think this idea of build here, you know, build local but but but think global is a really great way to think about how to build a company based in Canada. Harley, one of the things that we talk about as much as we

possibly can on this show is how artificial intelligence is just finding its way into absolutely every sector of our economy. Earlier today, we had a conversation with someone I work with in a wildfire modeling and predictive modeling software company to help mitigate risk. Talk to me about how AI is informing the growth of Shopify.

Yeah, look, this sort of AI rush feels like a decade's equivalent of innovation. Yeah, look, this sort of AI rush feels like a decades equivalent of innovation. It's unbelievable. On Sunday morning, my best friend David Siegel and I had this podcast called Big Shot, where we interview the most iconic Jewish entrepreneurs of the last half century. People like Izzy Sharp, who built the Four Seasons,

or Eddie Sunshine from Rio Can, or Charles Bronfman. I got a chance to interview Mickey Drexler recently, who built The Gap in San Francisco. And he told me that they used to, but 300 people at the Gap that were doing merchandising, photography, product descriptions. And I showed Mickey what actually we're doing at Shopify with Shopify Magic, which is our AI tool,

which comes included in, you know, your basic $39 a month charge with Shopify. That particular functionality is better right now. There's no additional cost form. This isn't a picture of Shopify, but it's built in. That is better than what 300 merchandisers were doing at the gap in the 90s. That is incredibly democratizing.

So the technology is really cool. What's even more important is it creates more of a leveling of the playing field so that more small businesses can get bigger faster. And I think this AI boom will be good for everyone. I think it'll be especially good for small businesses. Well, and that's a thing that I find really fascinating about what you've given entrepreneurs. Like if I want, if I was an entrepreneur and I had a passion for making t-shirts, I know

that I'm making the best t-shirts. That's why I'm going into business. I'm going to compete with everybody and people are going to buy my t-shirts because they're the best. The one thing I don't know is how to run a business that allows you to sell those t-shirts. Exactly, whether it's transactions or inventory or marketing or analytics, these are store design. I mean, what I think Shopify does and what AI does even better together with Shopify is we're creating this unfair advantage

in lowering this barrier to entry. And I think you're gonna see a lot more startups, a lot more businesses created during this AI era than ever before. And that is the most exciting thing ever. And more importantly, I think we'll see more people doing it from Canada. I've never been more bullish on the Canadian economy

or frankly, the community of Canadian entrepreneurs. It feels like there's a renaissance happening now. And you're seeing it in Montreal at Startup Fest last week or a month ago at Toronto Tech Week. There was this great desire to build huge, important, impactful things in Canada that I hadn't seen previously, especially in the last five years. Yeah, but Harley, talk to me about when AI reared its head

for the first time and you as a company were like, oh, we're gonna have to pay attention to this. Like, did you know instinctively how you were gonna fold sort of this notion of AI into Shopify, because every company has to do it, right? There was, there were all these really funny memes of, of, uh, you know, people just getting millions of dollars in investment just by saying they had an

AI company. Um, so like, did you guys know what to do with it at first or did you have to take your time? How did you guys square that circle? We tend to be early adopters with new technology, whether it's things like crypto and stable coins, which were embedding into our checkout now, or certainly with AI and large language modeling. The reason that it was, it became, it was sort of more organic for us because we always sort of knew that there were, let's say an entrepreneur has to do 20 tasks per day to run their business. Back to your t-shirt example, we want you as the entrepreneur to focus on your t-shirts.

That's what you do very, very well. But there's all these other things, for example, like shipping and inventory management and setting up new campaigns and doing bundling or doing product descriptions or taking great product photography. All those things entrepreneurs are forced to have to do when they're getting started as a small business.

They don't have a big team. So we began to look at, and this is going back probably five years, as AI was starting to rear its head out, how can we implement and make these tasks automated, whereby the entrepreneurs could focus on making t-shirts, not on configuring their marketing campaign on Meta or Instagram or something like that.

And actually, as things got better, we realized, wait a second, we can not just have an AI product inside of Shopify. We can embed AI across every piece of feature we have. And the end result is you're seeing these companies that some of them started five years ago that are now dominant, you know, like incumbents in their verticals.

We've never seen this pace and velocity of growth before and technology is driving that. So if I'm an entrepreneur and I wanna start a business and I've decided I'm gonna go the route of partnering with Shopify to do that, is it, I mean, I'm not trying to do an ad for Shopify, but is it, it's never been easier to start a business sort of thing?

If you know how to use email, you can build a Shopify store in a couple of hours. Now that's not to say it's going to be, you're going to be successful, right? Most small businesses don't end up being billion dollar companies. The key though is that the cost of failure right now, you know, July, 2025 is the lowest it's ever been for entrepreneurship. Go back to my grandfather's story. If the egg stall at a store at the farmer's market, when he got off the boat from Hungary was not successful, he would have lost his house. Whereas today, when you look at companies that you admire,

Veori or Allo or Canada Goose or Lulu or all these companies, these companies in most cases, they were not their first businesses. In most cases, they tried a couple things and then eventually something worked really well. The reason that they can do that is because the cost of failure is so low,

the barrier to entry is so low. So if you're sitting there listening to us talk right now, and you have this idea in the shower every morning keeps coming up, my advice to you is go try it right now. This is the greatest time ever to try starting a business. And your business may become a multi-billion dollar company, or it may not really work,

or it may just be a hobby you keep on the side. But that's part of what makes entrepreneurship so amazing, is that it provides a different level of success to different people depending on what they need. And I'm a card carrying member of the entrepreneurship club. I think entrepreneurship is the greatest way for humans to find their versions of success,

to make their lives better. And there's never been a better time to do so, whether you do a shop light or you do it with another company. Harley, this is exactly the conversation I wanted wanted to have I wanted an optimistic conversation. I wanted I want an optimist. I know you are man. This is exactly the tone. I want to strike I want people to be bullish. I want people to be ambitious I want people to take risks and I guarantee you you got somebody off the couch today. So thank you so much

I hope it's not the last time let's go. Let's let's go brother. Thank you so much and thank you for listening. We will see you back here tomorrow.. That's a finance offer that's better than other Japanese and Korean competitor SUVs. Hurry into your local dealer and drive away in the award-winning Nissan Rogue. Conditions apply. See Nissan.ca for details.