What does it take to transform a startup into Canada’s second-largest company in just a decade? Sonia Sennik and John Stackhouse discuss his conversation with Harley Finkelstein, President of Shopify, live from C2 Montreal.
Harley discusses how Shopify embraced anti-fragility, continually reinvented itself beyond e-commerce, and leveraged AI to reshape retail and empower creators globally. He highlights the essential entrepreneurial mindset needed to foster innovation in Canada, urging ambitious entrepreneurs to think bigger, build stronger networks, and seize the opportunities emerging at the forefront of technology and commerce. Tune in to explore how crises become catalysts, why relentless ambition matters, and how Shopify’s success story could inspire Canada’s next wave of global companies.
John Stackhouse: [00:00:00] Hi, it’s John here
Sonia Sennik: And I’m Sonia Sennik, CEO at Creative Destruction Lab.
John Stackhouse: This is Disruptors x CDL: The Innovation Era.
Sonia, it’s conference season in Tech Land. They seem to be everywhere, every day, all at once, all over North America, from the Google and Microsoft Jam Fest to the upcoming Toronto Tech Week. I just got back from one of them C2 in Montreal, which is all about the creative class meets technology, and I got to interview on stage, our old friend and one of the first disruptors guests.
Harley Finkelstein, the president of Shopify, and a force of nature in the Canadian tech conversation.
Sonia Sennik: The trajectory that Shopify has been on for the last 15 years has been tremendous. You actually interviewed Harley on the anniversary of their IPO. Can you think back 10 years ago to what Shopify was like before they [00:01:00] became the public powerhouse that they are in Canada?
John Stackhouse: $3.50 is what springs to mind. I think that was the IPO price and yeah, it’s now in the $150 range or. Maybe it’s higher today, I don’t know, but it has been one of the great Canadian rocket ships. So let’s have a listen. Here’s our conversation recorded live at C2 in Montreal. Good morning.
I’m John Stackhouse with, uh, RBC here with my good friend Harley Finkelstein from Shopify. We’re gonna have a great conversation about Shopify, a bit about Harley, but mostly about entrepreneurship. And what we need to come to grips with at this amazing moment of time. We are recording Live for Disruptors, an RBC podcast.
So hello to people far and wide who are listening to this as well. Harley is a repeat guest on Disruptors. So Great to, I was one of your first guests, I think actually. Uh, you, you were an OG. Yeah. In fact, this is an auspicious day. For a [00:02:00] few reasons. May 21st, 2015, 10 years ago, today, Shopify went public.
That’s true. So congratulations Harley, and to the team at Shopify.
Harley Finkelstein: Yeah. 10 years ago, almost to the minute we rang the bell in New York Stock Exchange. And for all of you in the crowd that are entrepreneurs, you know that there’s no feeling in the world, uh, like ringing that bell where people like Henry Ford once stood and it’s been an amazing ride.
John Stackhouse: And just to give you a sense of the ride, a billion dollar valuation, then 10 years later about $150 billion,
Harley Finkelstein: Something like that. Yeah. Give or
John Stackhouse: take. Give or take. Looking back 10 years,
Harley Finkelstein: what’s been most surprising for you? Well, I mean today the largest company in Canada is RBC. The second largest company in Canada is Shopify.
Just saying it out loud, we’re the second largest company in the country is is unbelievable. So that I think, obviously sticks with me. The other thing that sticks with me is just the impact we’ve been able to have. Shopify now powers somewhere in the neighborhood of 12% of all US e-commerce. We cross a trillion dollars in sales on the platform like trillion with a T, [00:03:00] and pretty much other than Amazon, we are the largest checkout on the internet.
So from a business perspective, obviously that’s been remarkable. But the other thing has been the amount of people at Shopify that are still around. We’re now about 8,000 or 8,500 people at the company, and there is a lot of OGs that are still doing their life’s work at Shopify 10 years later. It’s been an amazing ride.
So many critical points along the way. If you had to pick, uh, one, what would it be? I think the pandemic was one of those moments that I think in any entrepreneur’s life, similar to IPO, that you can forget overnight. This is something that most people don’t know, but I. Everyone thinks e-commerce is obviously a huge part of the economy, which it is, but e-commerce as a percentage of total retail is still in Canada, like 16%.
So part of what happened with the pandemic was overnight, the entire physical retail world shut down and all of a sudden everyone kind of woke up and realized that the future retail is not just offline, it’s, it’s online, it’s offline, it’s on social, it’s everywhere. We’re operating now is not just as an e-commerce company for small business, but rather as the [00:04:00] world’s commerce company.
If you look at the top five companies by market cap in Canada, um, RBC was created in 17, 1800, something like that. It was 1800. 1800, 1800. We’re not, we’re not that old. I know. Sorry. Excuse me. 1800, 150 years old, 150 years old. So other than. Shopify. The youngest company in the top five market cap companies in Canada was created in the fifties, which was TD Bank 1950s.
So for us at least there, there is a real sense of responsibility that not only do we want Shopify to continue to become a leader in Canada, but also how do we inspire the next vintage of incredible entrepreneurs, many of you who are in the room right now, to actually build these global dominating companies from here in Canada.
John Stackhouse: Uh, I just take, take a detour here on this point about age, because we’re only as old as, uh, we let ourselves be because our RBC is 155 years old. We consider ourselves the youngest bank in Canada, and that is very important. There’s a corporate biography. The title is Fast to the Frontier, and that is a mindset if there is a frontier.
We get there [00:05:00] before the others do. So let’s pivot to this idea of the entrepreneurial mindset, not just for individuals, for entrepreneurs, but also for a country. And how can Canada be more entrepreneurial and be more of a builder nation, which is what entrepreneurs are. So give us a glimpse of Shopify and how you maintain that builder and entrepreneurial mindset.
Harley Finkelstein: I mean, part of it is the love of ambition, but the other part is, I dunno if you folks know this book, but there’s this great book by Naim Telleb called Anti-Fragile. You and I talk about this book all the time. So this idea of anti-fragility is a fascinating model because most people assume that there’s sort of two types of systems.
There’s fragile and there’s durable. So you take a glass. You drop it and it breaks and it’s fragile. Take a glass and you drop it and it doesn’t break and it’s durable. But there’s sort of this other system called anti fragility, which is effectively you drop the glass and the glass actually reshapes stronger than it was in the first place.
We’ve taken that approach to Shopify in many ways. We’ve tried to, you know, name your podcast. We’ve tried to disrupt ourselves. So one of the things that I think historically we were [00:06:00] known for is e-commerce. We actually do not think we are an e-commerce company. We think we are a commerce company. We think the future of retail will be retail everywhere.
And the big change between retail 30 years ago in retail today is not that you have new channels, whether it’s. Social commerce, or we just announced a partnership with Roblox. So now if you’re on Shopify, you can literally sell products in Roblox, which is a big deal because there’s a hundred million people living in Roblox digitally every single day.
What we realized was that what is happening now is consumers are dictating to the retailers how they wanna buy the retailers and the brands that are gonna be most successful will sell wherever it’s most convenient for those consumers. So we started to go into things like physical retail. We started to go into things like social commerce.
We constantly thought about what is the next version of Shopify? Not like next year’s version, but in 10 years from now, what it’s gonna look like. That’s the first thing. The second thing is probably one of the best venture capital firms in the planet is Sequoia. Sequoia passed on Shopify in 2010, and when you ask Sequoia why they passed, they will say, [00:07:00] ultimately, we had an issue with your TAM, your total addressable market.
At the time, in 2010, there were about 16 million retail SMBs in the world. So they basically said, well, Shopify has 2000 of them or 5,000 of them. We think that’s, that’s good growth, but that doesn’t necessarily mean they’re ever gonna be a billion dollar company. The way we saw it though was that rather than simply just growing our slice of the pie, we were trying to grow the pie itself, and I think what would due respect to Sequoia, what they missed was that.
We were actually creating new entrepreneurs, not just taking the larger market share from the existing base of entrepreneurs. That’s kind of the way we’ve always thought about things. How do we actually disrupt ourselves? So e-commerce is cool. What’s next? Where’s retail going? And maybe the, the last one I would say is that.
We don’t lick wounds very often. We have a lot of different areas of our business. We have a payments business as a standalone company. Shopify Payments would be one of the largest companies on the planet. We have a capital business. We have a shipping label business. We had a shipping and fulfillment business for a while.
It didn’t work. We shut it down. We moved on. We [00:08:00] believe failure is the successful discovery of things that did not work. And I think when you apply that lens to decision making, you end up making much better decisions and you end up growing faster. How do you assess failure as an organization or as a team?
It’s one of two things. Either it’s product market fit or it’s simply we don’t have the right team in place. And so in the case of fulfillment, for example, if you were to pretend that Shopify was a single retailer, you aggregated all of our stores into one single large store, we would be the second largest online retailer in America.
Amazon will be the first shop, be the second. We decided, uh, years ago that what if we actually acted like that as if we were the second largest retailer and then went ahead and tried to get economies of scale across every single pain point that a retailer might have. And so fulfillment was a pain point.
We thought if we build our own warehouses and we build our own fulfillment companies, three PL capabilities, maybe we can make that easier. At some point we realized that bits and bytes and atoms are very, very different. We’re really good at building software. We are not very good at building physical infrastructure.
And so we looked around and figured out [00:09:00] is there someone out there that is doing fulfillment in a way that we would love to emulate? In the case of fulfillment, there was a company called Flexport. And so we decided to, rather than do it ourselves, sell it all to Flexport. And now the thing that was a side quest for us is a main quest for them.
That’s kind of how we look at these things that don’t necessarily always work is, is there someone out there that can do this better than us, but we can still participate in the upside.
John Stackhouse: I wanna go back to the anti fragility point and link that to recruitment, because recruitment is a huge part of Shopify. As part of your culture, how do you recruit for anti fragility?
Harley Finkelstein: We have a little bit of a hack that all of you are welcome to steal from us, which is that. Ultimately, if you look across the company, most people that work at Shopify, again, Shopify is an entrepreneurship company.
The software we build, the products we care about, it’s all about entrepreneurship. Often what we end up doing is we end up hiring entrepreneurs. We look for founders. So [00:10:00] if you’ve met people that work at Shopify, the first question you can ask them as a test is, have you built your own company? And almost everyone at Shopify would say, yeah, I have.
Sometimes they’ve been very successful and we’ve acquired them. In other cases they said, yeah, I tried. It didn’t work. Looking for people that are actually founders, we have found to be the best type of DNA for people that to come work at Shopify. They seem to have the, uh, more of an anti fragility mindset about building, but more importantly.
They have been affected by entrepreneurship to the extent that falling in love with the mission of Shopify, which is about increasing the surface air of entrepreneurship is a lot easier. And so we recruit for that. We’ve now opened up our offices on Sundays. I told you we called it Builder Sundays. So every Sunday in Montreal, here and in Toronto, the Shopify office is open.
Any entrepreneur can come hang out, and for those of you that have been you, you know that I come hang out, I spend a couple hours every Sunday there. I’ll answer emails or I’ll work on a talk or something like that. That’s the best way for us to actually find incredible people that may wanna come work at Shopify, or in the worst case scenario, people [00:11:00] that wanna build apps for Shopify or build teams for shop, or be part of our ecosystem.
That ability to actually recruit founders to build software for other founders, that’s been the best thing for us on the recruiting side.
John Stackhouse: You mentioned total addressable market, TAM and how a lot of people don’t get that. They don’t get that. In a lot of companies, a lot of entrepreneurs are not good at explaining.
Yeah. Uh, explaining their TAM. How do you see TAM today for Shopify?
Harley Finkelstein: The clever answer that I’d like to say is it should be the same TAM as Oxygen, which is anyone, but ultimately it is someone that wants to sell a product to somebody else. Historically, the stores on Shopify, the businesses that we worked with were these startups, these small companies that started at their mom’s kitchen table that grew really large.
And if you look at companies like Aloe Yoga or RI or Gym Shark, that was their story. But now we’re seeing companies like Yellow and Mattel and Birkenstocks and on running also come to Shopify as well. Ultimately. What we’re trying to do is make it so that if you have something of value that you wanna share with someone anywhere in the world, on any single surface area, and that might be e-commerce, that may be [00:12:00] ai.
I mean, I think what’s one of the things that’s gonna happen in the next couple years is you’re gonna see the shift from searches, stop starting on search engines to search starting on. Chat GBT perplexity code. And that’s a huge opportunity. And so our responsibility is if you’re on Shopify, wherever someone is looking for your products, we make sure you show up.
So our TAM is is not a particular segment or a particular type of channel. It’s anyone that wants to sell something to anybody else. And so one is to helping existing entrepreneurs, but also helping aspiring entrepreneurs convert that idea in the shower into a real business. So if you think about the history of of commerce, the history of retail, the way it always started was first you build a product and the new found audience go back 150 years.
You’re the baker, you make bread, you then do some marketing. You get people to come into your bakery, you sell the bread. That’s how it always worked for the first time in the history of the world. What’s happening now is someone like Hailey Bieber. Who has a huge audience is able to create Rhode Beauty.
R-H-O-D-E. She created a cell phone case for your [00:13:00] iPhone that allows you to put your lipstick in it. So she has an audience. She understands her audience. She decides I’m gonna create a product specifically for this audience, and she creates a hundred million dollars company in a matter of months. This idea of shifting the sequence of events from product first, audience second to being audience first, product second.
That is some of the coolest thing ever that that’s ever happened in entrepreneurship.
John Stackhouse: Take us deeper into the AI aspect of this. How is AI going to change that, or how is it already changing that dynamic of creator and market?
Harley Finkelstein: There’s some obvious ones which around leverage you. You know this, and some of you in the crowd know this, but when I’m not a leading Shopify, my Sunday project is I have this podcast called Big Shot where I’m creating an archive of the greatest Jewish entrepreneurs.
One of my last episodes was a guy named Mickey Drexler. He’s about as close to retail royalty as it comes. He created Old Navy. He basically created J Crew. He ran the Gap for 20 years. He was on the board. Steve Jobs and him were very close friends. He was on the board of Apple. Mickey Drexler talks about that.
In the heyday at the Gap, there were literally hundreds of [00:14:00] people working in the product photography Department of the Gap. I. Doing product descriptions, product photography, merchandising. Today, it’s not a pitch for Shopify. Shopify is $39 a month. You get better tooling and a better quote, unquote helper or co-founder with a free product that we give you as part of Shopify than Mickey had at the gap with 300 people.
So that’s the obvious stuff that like technology is gonna make product descriptions and product photography much easier. But the much larger picture is that right now, if you go to Google and you type in sneakers. The first search result you’re going to see is Footlocker. It’s because Footlocker pays for that.
I believe in a few years from now, when you go to chatGPT or Perplexity or any of these amazing AI tools and you type in sneakers, they’re gonna look at all of your history of every search you’ve ever done on that particular platform, and they’re gonna say, you know what? That guy really likes running or hiking.
I’m gonna show him. Adams, Allbirds. I’m gonna show him ON running. I’m [00:15:00] gonna show Birkenstocks. All of a sudden now, consumers are getting products that actually they care about based on their particular search history, not who has the most amount of money. I. And for any of you in the room right now who sell product, particularly online, that is the biggest fundamental change like paradigm shift in 20 years of e-commerce, because now it’s not who has the most amount of money, it’s actually who can get in front of the most amount of customers.
And I think that is incredibly disruptive, but also incredibly democratizing.
John Stackhouse: So let’s shift to what Canada needs to do to seize this moment. ’cause it is a moment. I’m not sure there’s ever been a better time to be a creator. Yeah. In the world. There’s all sorts of challenges, but. Classic frictions are being removed hour by hour, minute by minute, and we just talked about what AI can do to reduce friction.
Yep. Interestingly, here in Montreal, there’s one of the greatest concentrations of creators in the [00:16:00] world. I think YouTube has more creators, producers in Montreal per capita than anywhere else. More gamers and game creators here in Montreal. The same can be said across Canada, and yet clearly we’re not creating enough value from that. What are we missing?
Harley Finkelstein: Well, first let me just say this, I’ve spoken at C2, I dunno, four or five times in my life. This is actually the first time I met C2 living in Montreal. I moved to Montreal 18 months ago because I think Montreal is by far one of the most entrepreneurial cities, not in Canada, on the freaking planet.
This is a place that praise of the altars of entrepreneurship. There is no place like this city, especially as someone that is an entrepreneur. I love this place.
The Canada thing. Part of what I think is missing here, and just look at the last 48 hours, there’s been two op-eds published, one in the globe and one in the financial posts. One says, is Canada a legitimate trading partner? The other one says, is Canada a real economy? So. I [00:17:00] think generally most people in the crowd are probably tired of hearing what the problems of Canada.
We get it. There are issues with the country, we can get better. We have a new government. We have a much more ambitious leader, I think here, and I think there’s a lot of momentum right now in Canada. So I don’t wanna talk about the problems of Canada. I think we talk about the opportunity. I think the opportunity is that ultimately if you’re a creator or you’re an entrepreneur.
There’s no reason that you cannot live in any of these amazing cities in Canada. There’s no reason that your audience, that your addressable market needs to be here too. In the same way that if you are a tech entrepreneur and you have to raise venture capital, you can look at great Canadian VCs. You can also look at great American VCs or European VCs or Asian VCs or Latin American VCs.
Businesses now geographically agnostic. When you look up something on Perplexity or chat GBT, and you’re looking for a pair of shoes and the shoes that come back up, you don’t ask yourself, where is the founder based? You ask [00:18:00] yourself, is this a product I wanna purchase? Yes or no? If it’s yes, click to buy, hopefully on shop pay.
If not, you move on. So I think one of the things that we need to just remember is that. This may be a smaller market than our neighbors to the South, but Shopify, most of our merchants are in the US. Most of our partners are in the US. The original venture capitalists from Shopify were American VCs.
Canadian VCs are also involved, but ultimately we were agnostic. I was born in Canada. I grew up in the States, Tobi’s born in Germany. We never looked at Shopify as being a company that needs to be focused on Canada. We were a company based in Canada, and although those sound similar, those are very, very different things.
RBC capital markets and your investment banking arm on Wall Street. You guys don’t wanna be the best Canadian investment bank on Wall Street. You wanna be the best investment bank. Full stop. And I think the companies that are most interesting, like Fullscript in Ottawa, or plus grade here, or I think about Cohere or League, uh, or Clio in Vancouver, all these guys running those companies, [00:19:00] they are not building.
Companies focus on Canada. They just happen to be building from Canada and they wanna be the best in the world, and they’re leveraging this incredible place. I think that’s not a major aha moment, it’s just a different way to think about ambition.
John Stackhouse: I can feel the energy from you here on stage. What do we need across the country? To force multiply this.
Harley Finkelstein: I think more role models are really, really important. I mean, I mentioned that builders Sunday, as at Shopify, brings in founders to come work in our office who want to. No strings attached, but selfishly, I also wanna meet these people.
I wanna hear what they’re doing. I wanna see what they’re excited about. I feel a responsibility to show up on Sundays, just to remind them that this office, they’re in Shopify, was not built overnight, nor was it built by having small ambition. The second is, you know, you started this, our session today by talking about the 10 year anniversary of [00:20:00] Shopify.
Anyone that has messaged me to say we are close. In IPO, I’ve pretty much stopped everything that I’m doing day to day and said I’m going to like come up to Montreal or come, I’ll meet you somewhere. I will give you the exact roadmap of what you need to be IPO, ready, company, team, bankers, lawyers, governance, whatever you need, I will deliver you in a silver platter.
I will not hold back. I will tell you the cheat sheet of how to do it because I actually think. Like success gets more success. We need more op-eds about what can we do given the current situation we’re in right now. And I think talking about anti fragility, talking about admission, celebrating our successes here.
You know, on the IPO roadshow, which was a 10 years ago, we were on the IPO roadshow. We did 93 meetings, probably 40 of those 93 meetings. Someone mentioned to us, oh, you’re Canadian. We haven’t seen a company from Canada since North Teller Rim. That wasn’t a compliment. They were sort of insinuating that companies in Canada, you know, don’t last.
We’re gonna be here in another 10 years and 20 years and 30 years, Shopify’s not going [00:21:00] anywhere. So again, like change that narrative that American investors think that just think of RIM or think of Nortel instead of thinking about Shopify. I think of us thinking about RBC instead of thinking about cohere.
I think that will help a great deal too.
John Stackhouse: By the way, just an observation for the crowd and those listening. Uh, Harley and I did our first fireside a little more than 10 years ago. It was before the IPO and Shopify was known then. You were known a little bit then, but early, early days. I was impressed then and more and more impressed over the decade about how you are.
Just irrepressible number one, but you, you power your network. You will reach out to, I’m guessing almost anyone, anytime for pretty much anything legit that is helpful to you, but also has a bigger purpose. I’ve seen you do this and not enough people will pick up the phone, even metaphorically, and just reach out to someone and say, can you help me?
And. What are the odds of someone saying yes?
Harley Finkelstein: Yeah. Uh, to that they’re not zero because we don’t have the quantity of population in Canada like they do in other places, in other countries. What we [00:22:00] do have is relationship. We actually have people here. There are, I’m looking around the crowd. There are a dozen people in this crowd right now who have helped me in my career.
Mitch Joel’s in the back when I was setting up smoofer, which was store number 137 on Shopify. Before I got to Shopify, I was one of the first merchants. Mitch Joel was running twisty mod at the time, sat down with me and said, here’s everything you need to know about digital marketing. He didn’t know me, he didn’t have to help me.
He did it because he gave a shit. And if all of us give a shit and we do this at scale over and over again, we’re gonna win. It’s kinda like a total addressable
John Stackhouse: market, but it’s not the market, it’s the supporters. That’s right. Like your, your team is almost infinite if you let it, uh, if you let it be.
Harley Finkelstein: That’s right.
That ecosystem reciprocity. That’s where this stuff gets really good. I get this call. We wanna build more Shopifys. Everyone in this room could build another Shopify. Tobi and I are not smarter than anyone in this room. We work really, really hard. We are incredibly disciplined. We’re very, very ambitious.
We just really. We give a shit, we really give a shit about Shopify being an incredible business product and company. I wanna share that with everyone that needs that from me.
John Stackhouse: So we’ve got just, uh, two minutes [00:23:00] left. Uh, how do we create that flywheel in Canada? And I think an important reference point is the value that Shopify has created gone from 1 billion to $150 billion.
That’s not a gold bar sitting. In a vault somewhere that is spread across thousands of people, largely here in Canada, I’m guessing, who are reinvesting, who are building other assets with that, as well as building Shopify. So we need more of that flywheel wealth creation. It’s not a bad thing, it’s a great thing.
Harley Finkelstein: And celebrating success like that is a great thing too. What we need to, so, you know, spin the flywheel. What John’s referencing is before we came on, I showed him a slack message on my phone from someone who now lives in TMR here in Montreal. And. This woman joined Shopify 12 years ago. I posted a photo of the IPO and she wrote me a note and said, my life has forever been changed by that particular day at the IPO.
That her life, her children’s life, her family’s trajectory for the next three generations has been changed by it. If anyone knows me and my background, my [00:24:00] family’s background, our story of, of immigrating to Canada, you know, like that hits hard for me. I love that stuff, but I think that is like sharing in the upside every single person that Shopify has equity.
Everybody, not a single person design of equity. So not only helping Shopify become a bigger company, but also I think we’ve created, I don’t know, 700 800 millionaires, people at Shopify that are now millionaires because of the IPO. That means that if they stay at Shopify, great. If they don’t, they may leave and they may be angel investors.
They may start another company. That stuff really matters. And so for those of you that are sort of the early stages, considering how to think about equity and your option pool, be really generous. Help that flywheel exist because getting a note like that from someone saying their family’s trajectory has been changed because of a single pushing of a bell in New York City 10 years ago.
That is what is exothermic energy gets distributed and then they get to distribute to other people as well.
John Stackhouse: That’s the magic of human capital and financial capital totally combining, which is the Shopify story. Um, last question. If we are fortunate enough to be here in 10 years time. What do you hope to be able to [00:25:00] say?
Harley Finkelstein: Well, there’s never been a trillion dollar market cap company ever been created in Canada ever before. I think obviously RBC is the largest, uh, I’d like you to say the largest. If there, there’s a bit of a curse, as you probably know, of companies that eclipse RBC from a market cap perspective, but there’s never been a trillion dollar company created in Canada ever.
Uh, there’s eight in the US or someone like that. I think I would like in 10 years from now for there to be a trillion dollar company in Canada. I’d love it to be Shopify, but I’d also be very proud if it’s one of you in the room who ends up doing that.
John Stackhouse: Let’s do it. Yeah. Harley, thank you so much. Thank you.
That was my conversation with Harley Finkelstein at the C2 Conference in Montreal, Sonia. It’s hard to be with Harley and not feel like you just drank a case of Red Bull. The guy has more energy than almost anyone I know he likes to call himself a power extrovert, but behind that extroversion is a lot of thinking about technology, about companies, about [00:26:00] startups, and about entrepreneurship. We sure need a lot more of that in Canada.
Sonia Sennik: John, one of the things I loved that Harley said at the end was about the importance of exothermic energy and creating relationships and networks that start to build upon themselves and create that flywheel effect. You could just sense his energy and his enthusiasm for entrepreneurship spending time on Sundays just with an open door at the Shopify.
Headquarters meeting entrepreneurs. That type of excitement for entrepreneurship is something that is rare and even more rare to see it 15 years into his journey as president at Shopify.
John Stackhouse: Yeah, I love that innovation of opening your doors. I’ve often called it mingling, and many of the best leaders I’ve known through the years have been mingler.
They mingle with their clients and potential clients. I used to know A CEO who would spend an hour a week. As a customer care person just to take complaint calls from his customers because he wanted to have an honest conversation. They [00:27:00] had no idea they were talking with the CEO, but for him it was this superpower of learning and business history is full of great leaders, innovators, and builders who perfect that art of mingling.
Sonia Sennik: A quote from your conversation with Harley that really stuck with me was fast to the frontier. And how important are networks and relationships when you’re looking to be fast to the frontier in any new emerging technology?
John Stackhouse: Yeah, you’re not gonna get there on your own. So find the force multipliers in your network or add them to your network.
That was something I’ve also learned from Harley in this conversation and in knowing him over the years, is he’s a power networker and not ashamed about it. And maybe a last point to refer to is the importance of crises in building a company. We don’t wish crises on anyone, but they come. And great companies.
Shopify is one of them. The global financial [00:28:00] crisis as a catalytic moment for Shopify before it IPO’d, and then of course the pandemic, which was another inflection point for it. But it became an inflection point because they made it an inflection point to many of us run to our basements, lock the door, and wait for a friendly knock rather than see it as.
What I’ve heard described is a blue water opportunity, and that means creating more blue water between you and your competitors.
Sonia Sennik: It’s so clear in listening to Harley’s story that Tobi and Harley were so incredibly focused. He talks about their work ethic, their discipline, and very humbly says, we’re not any smarter than anyone in this room.
We just knew what we wanted to build, and we’ve been relentless about building it. Tying that back to his conversation about the importance of networking in this world of hyper productivity where all of our calendars are stacked from morning to night. In the innovators that you’ve met with the CEOs that you talked to, how best for people to carve out that time and ensure they’re investing in relationships?
What have you [00:29:00] learned in all the conversations you’ve had, John?
John Stackhouse: Well look for those gifts that knock on the proverbial door, seeing someone in a room or in a hallway, or in an airport, and taking the opportunity to introduce yourself, seize that moment, and then keep the word relentless in mind, partly shows, and Shopify as a company, shows that you need to be focused, as you say, and just relentless in your pursuit of growth.
Not for growth’s sake, but for constant improvement. I love the reference from Tobi from way back when, where I think he says if you’re not growing 40% a year in whatever it is you’re doing, you’re stagnating. Wow. That’s a, uh, that’s a high bar. But uh, these are folks who keep raising that high bar higher and manage to keep clearing it.
And that is what has made them the most successful, dare I say, technology company in Canadian history. And part of that we should stress is Harley’s point that they don’t see themselves as Canadian. They happen to come from [00:30:00] Canada, but they’re global and we all need that mindset a little bit, maybe a lot more.
Sonia Sennik: And how you talk about yourself matters. I loved when he said that before they were even considering being on the list with the likes of Amazon, they were designing their company as if they were already the second biggest marketplace in the world and started building for scale well before they were there.
And I think if we can get more of that conversation in. The ecosystem of reciprocity of that network of entrepreneurs in our country think we’ll be in really great shape.
John Stackhouse: The mic drop moment, of course, was his reference to Canada needing a trillion dollar company. And why not Shopify? What a great ambition.
We’ll see if they get there. Let’s hope they, and many others do get there, but you’re not gonna get there if you don’t have that. Ambition. So thanks again to Harley for spreading the ambition and coming back to Disruptors. This [00:31:00] is Disruptors, an RBC podcast. I’m John Stackhouse.
Sonia Sennik: And I’m Sonia Sennik.
John Stackhouse: Talk to you soon.
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