The Exchanges

Q Final one, and then we'll do a quick fire, but what changes have you actually made to be that present, loving, real father that you wanted, not just the superficial?

A A couple easy things. I like to work out every day, but I'd kind of work out whenever I finished work, and so, you know, I'd be here in my, I'm in my home office here, I'd be here, and then, I don't know, six o'clock, or six 30, or something, 7:15, I'd go to the gym, work out for 45 minutes, then go up to dinner, and I'd almost always miss the kids. Zoe would be sleeping by then, or Bailey would be in bed by then, and I just, I couldn't figure out how to do this, because it was important for me to work really hard and get, you know, finish my day, finish the work. It was important for me to get some exercise in, because I just feel better when I work out, and it was important for me to see my kids, and it felt like I had to choose, and so what I did was instead, I just hired a trainer. Initially, it was virtually, now it's, now it's in person, who every day at 5:30 would show up at the house, and I recognize that not everyone, you know, I wasn't able to afford that, frankly, up until very recently, but, you know, Like, even, you know, everyone has, a lot of us have Pelotons. My suspicion is most of us do the on-demand classes, not the scheduled classes, but actually, if you have to do the scheduled classes, because you have to show up at four 30 or five 30, it means that is blocking it off, and so now, I finish my day by five 30, because that's when the trainer shows up, or yog…

AI assessment note: “what I did was instead, I just hired a trainer”

Q Final one, and then we'll do a quick fire, but what changes have you actually made to be that present, loving, real father that you wanted, not just the superficial?

A A couple easy things. I like to work out every day, but I'd kind of work out whenever I finished work, and so, you know, I'd be here in my, I'm in my home office here, I'd be here, and then, I don't know, six o'clock, or six 30, or something, 7:15, I'd go to the gym, work out for 45 minutes, then go up to dinner, and I'd almost always miss the kids. Zoe would be sleeping by then, or Bailey would be in bed by then, and I just, I couldn't figure out how to do this, because it was important for me to work really hard and get, you know, finish my day, finish the work. It was important for me to get some exercise in, because I just feel better when I work out, and it was important for me to see my kids, and it felt like I had to choose, and so what I did was instead, I just hired a trainer. Initially, it was virtually, now it's, now it's in person, who every day at 5:30 would show up at the house, and I recognize that not everyone, you know, I wasn't able to afford that, frankly, up until very recently, but, you know, Like, even, you know, everyone has, a lot of us have Pelotons. My suspicion is most of us do the on-demand classes, not the scheduled classes, but actually, if you have to do the scheduled classes, because you have to show up at four 30 or five 30, it means that is blocking it off, and so now, I finish my day by five 30, because that's when the trainer shows up, or yog…

AI assessment note: “what I did was instead, I just hired a trainer”

Q a very good friend of the show, Harley Finkelstein, president at Shopify. Can I ask, you mentioned very openly, you know, not being a great husband in the early days. Do you think you've always been a great father? It's so hard, man. You're president of Shopify. There's 10,000 employees. Have you always been a great father, and have you had some lessons on what great fatherhood means to you?

A No, I have not. I'll give you the best example. I thought being a great father was on Saturday mornings when my kids wanted pancakes. Bailey calls brunch. She says, I want brunch this morning, which she means is pancakes and bacon and that sort of thing. Making the best pancakes is And having the best bacon, and setting the table really beautifully, that made me a great father. First of all, any of you listening have small kids, they don't give a shit about that. They don't care about how nice the table's set. What actually my kids valued more was my presence. Was I actually there, and was I mindful of them? In the early days, so I'd make these great brunch breakfasts, and I'd set up this nice table, and I'd get fresh squeezed orange juice, and make these great pancakes. I'd watch YouTube videos on, we have a flat top in our kitchen, which is a really cool thing to have, and I'd watch YouTube videos on how to make the best pancakes, and all this stuff, and I'd present it. And then like, You know, I'd be there, but I'd also be like checking email, or I'd, you know, I'd get a phone call, and it was during one of these couple sessions with Lindsay that the couple therapist said, well, Harley, are you a present father? And I said, yeah, you know, I gave all these examples, and the therapist and Lindsay Bo said, that is not what she's talking about. The kids don't value some special…

AI assessment note: “No, I have not. I'll give you the best example.”

Q say, I remember being super nervous. I asked my mother to unplug the home phones in case someone rang. I only had 50 dollars in my bank account, and then I started with Guy Kawasaki. I was super, super nervous, and so I had a chamomile tea beside me. And you bring in the essence That make it so much more familiar for people. Do you see what I mean?

A I mean, you're talking about the craft of storytelling, and I think the craft of storytelling is incredibly important. I mean, you, you, you run a very successful podcast. You sort of, by, by very nature have to be a great storyteller. The relationship that I have with Toby is effectively that in the same. I mean, Toby, I think is probably the greatest product, uh, mine on the planet. I mean, I just, I, I don't say that, um, boastfully. I say that from great, you know, with great insight and great experience working side by side with him for, you know, a third of my life. Um, my job is then to take what he builds and ensure the world knows about it. And the only way the world's gonna, gonna, gonna actually care about it is if I leave These, these breadcrumbs of, of storytelling and narrative. And, you know, if you, if anyone follows me on social media, I talk about Shopify's product a bit, but what I really talk about is our merchant story. Because for me, the way to deeply understand Shopify is to look at Ben Francis in 2013, uh, as a pizza delivery boy in London, uh, in college who decides to start Gymshark and to watch his journey to be one of the most important athletic brands on the planet in 2022. That, and, and the way to do it is not to just talk about his numbers, but I start with what he was doing before I begin to talk about, you know, why he didn't think that the ex…

AI assessment note: “you're talking about the craft of storytelling, and I think the craft of storytelling is”

Q You mentioned joining his board. What have you learned from a board member that you've worked with and why did that stick with you?

A Um, there's some like tactical stuff, you know, uh, Gail Goodman, who's on our board, she's an amazing entrepreneur. She ran constant contact for a very long time. You know, we'll, we'll talk about reorgs and she'll say things like, you know, the best part of a reorg is not the final destination, but the, the actual activity reorging, like companies that get really good at reorganizing reorging, uh, Are, are just more anti-fragile companies. So there's always practical stuff like that. Um, you mentioned Jeremy Levine earlier. Jeremy Levine is, is probably, uh, is one of the people I've learned the most from. One of the things that Jeremy does that I don't do very well is in board meetings, Jeremy will listen. So, uh, he'll be silent. He'll sit there and he'll listen and he'll wait till the end of hearing everyone's input. And then he'll comment on it. Um, that ability to sit there and just shut your mouth. Uh, and not say anything while you're acquiring more insight and information, and then turn that into something, ah, like, turn that into a better response or a better piece of insight. Um, I don't think anyone does it better than Jeremy Levine. He is, his, his ability to digest information and then process it is, is, um, unlike anything I've ever seen.

AI assessment note: “Jeremy Levine is, is probably, uh, is one of the people I've learned the most from.”

Q Final one, and then we'll do a quick fire, but what changes have you actually made to be that present, loving, real father that you wanted, not just the superficial?

A A couple of easy, uh, easy things, uh, were, you know, I, I, I like to work out every day, um, but I'd kind of work out whenever I finished work, and so, you know, I'd be here in my, I'm in my home office here, uh, I'd be here, and then, I don't know, six o'clock, or six 30, or something, 7:15, I'd go to the gym, work out for 45 minutes, then go up to dinner, and I'd almost always miss Uh, the kids. Uh, Zoe would be sleeping by then, or Bailey would be in bed by then, and I just, I couldn't figure out how to do this, because it was important for me to work really hard. It was, and get, you know, finish my day, finish the work. It was important for me to get some exercise in, because I just feel better when I, when I work out, and it was important for me to see my kids, and I felt like I had to choose, and so what I did was instead, I just hired, uh, I hired a trainer, um, initially it was virtually, now it's, now it's in person, um, who every day at 5:30 would show up at the house, And I, I recognize that not everyone, you know, I wasn't able to afford that frankly up until very recently, but you know, like even, you know, everyone has, a lot of us have Pelotons. My suspicion is most of us do the on-demand classes, not the scheduled classes, but actually if you have to do the scheduled classes because you have to show up at four 30 or five 30, it means that is blocking it off. …

AI assessment note: “what I did was instead, I just hired, uh, I hired a trainer”

Q Can I ask, you mentioned very openly, you know, not being a great husband in the early days. Do you think you've always been a great father? It's, it's so hard. You're president of Shopify. Um, there's 10,000 employees. Have you always been a great father? And have you had some lessons on what great fatherhood means to you?

A No, I have not. I'll give you the best example. Um, I thought, uh, I thought being a great father, here's a A perfect example of that. I thought being a great father was on Saturday mornings when my kids wanted pancakes, uh, or what Bailey calls brunch. Uh, she doesn't really, she says, I want brunch this morning, which she means is pancakes and bacon and that sort of thing. Um, making the best pancakes and having the best bacon, um, and setting the table really beautifully. That made me a great father. First of all, if you, any of you listening have small kids, um, they don't give a shit about that. They don't care about how nice the table set. Um, what actually my kids valued more was my presence. Was I actually there? And was I mindful of them? In the early days, so I'd make these great, you know, brunch breakfasts and it set up this nice table and I get fresh, squeezed orange juice and make these great pancakes. I'd watch YouTube videos on, we have a flat top in our kitchen, which is a really cool thing to have. And I'd watch YouTube videos on how to make the best pancakes and all this stuff. And I present it. And then like, you know, I I'd be there, but I'd also be like checking email or I, you know, I get a phone call and, and it was during one of these couple sessions with Lindsay that, um, uh, the couple of therapists said, well, Harley, are you, are you a present fathe…

AI assessment note: “No, I have not. I'll give you the best example.”

Q Which leader do you look up to and why?

A Hmm. It's so interesting. Um, you know, the obvious names that come up are sort of all these like tech visionaries and stuff like that, but I'm not really sure. Um, there's a guy named John Hope Bryant, uh, that I, I recently met. He runs, uh, Operation Hope. Um, I think he's one of the best leaders I've ever encountered. I actually joined his board recently and he's in Atlanta. His, his goal was to create, um, one million, an additional one million, uh, black entrepreneurs in the next decade or so. Um, I think he's just absolutely incredible. And the way that he thinks about everything from civil rights to economic, uh, independence is, is amazing. And what he does is, as he goes on his journey, he just brings all these other people along in the journey and finds a way to speak to them in a way that is so compelling. Even if they're not interested in everything he's interested in, he gets so many people on the boat with him in a way that I've, I've never seen before. And you can look up John Hope Bryan. He's amazing.

AI assessment note: “There's a guy named John Hope Bryant... I think he's one of the best leaders”

Q I mean, one very interesting question that, again, I have to admit, Aydin did give me, and it was talking about kind of big decisions and strategic moves that, at the time, didn't seem like a big deal, but in hindsight were actually game changers. Are there any that come to mind with that respect?

A I mean, probably the biggest one, you know, if you were to walk outside in any major street, at least I hope so, in any major street in the world, and you were to say, So to, to 10 random people, you'd ask them what Shopify does. Nine out of the 10 would say that Shopify enables e-commerce. And I think that's what we're best known for. But around 2013, 2014, it became increasingly clear to us that the future of retail is not binary. It's not online versus offline. Despite what you may hear from the CEOs of major malls and, and, and, and major retailers, the best spies and the, excuse me, the JCPenney's of the world, we didn't believe that these things were separate. And so we felt very passionately that the future retail is likely retail everywhere. That if you want to sell to a certain demographic, you have to have a great integration to Facebook or Instagram or Pinterest. And if you, if you want to sell to a different demographic, you better have a great integration, uh, or you better have a great point of sale in store experience. And another demographic may really want a great online experience, but maybe they also want a showroom. And the idea is that merchants and entrepreneurs are They need to sell wherever their customers or their potential customers are hanging out and customers and potential customers are hanging out everywhere. And so we felt strongly that, um, if th…

AI assessment note: “we felt very passionately that the future retail is likely retail everywhere”

Q Can I ask, you mentioned very openly, you know, not being a great husband in the early days. Do you think you've always been a great father? It's, it's so hard. You're president of Shopify. Um, there's 10,000 employees. Have you always been a great father? And have you had some lessons on what great fatherhood means to you?

A No, I have not. I'll give you the best example. Um, I thought, uh, I thought being a great father, here's a A perfect example of that. I thought being a great father was on Saturday mornings when my kids wanted pancakes, uh, or what Bailey calls brunch. Uh, she doesn't really, she says, I want brunch this morning, which she means is pancakes and bacon and that sort of thing. Um, making the best pancakes and having the best bacon, um, and setting the table really beautifully. That made me a great father. First of all, if you, any of you listening have small kids, um, they don't give a shit about that. They don't care about how nice the table set. Um, what actually my kids valued more was my presence. Was I actually there? And was I mindful of them? In the early days, so I'd make these great, you know, brunch breakfasts and it set up this nice table and I get fresh, squeezed orange juice and make these great pancakes. I'd watch YouTube videos on, we have a flat top in our kitchen, which is a really cool thing to have. And I'd watch YouTube videos on how to make the best pancakes and all this stuff. And I present it. And then like, you know, I I'd be there, but I'd also be like checking email or I, you know, I get a phone call and, and it was during one of these couple sessions with Lindsay that, um, uh, the couple of therapists said, well, Harley, are you, are you a present fathe…

AI assessment note: “No, I have not. I'll give you the best example.”

Q Final one, and then we'll do a quick fire, but what changes have you actually made to be that present, loving, real father that you wanted, not just the superficial?

A A couple of easy, uh, easy things, uh, were, you know, I, I, I like to work out every day, um, but I'd kind of work out whenever I finished work, and so, you know, I'd be here in my, I'm in my home office here, uh, I'd be here, and then, I don't know, six o'clock, or six 30, or something, 7:15, I'd go to the gym, work out for 45 minutes, then go up to dinner, and I'd almost always miss Uh, the kids. Uh, Zoe would be sleeping by then, or Bailey would be in bed by then, and I just, I couldn't figure out how to do this, because it was important for me to work really hard. It was, and get, you know, finish my day, finish the work. It was important for me to get some exercise in, because I just feel better when I, when I work out, and it was important for me to see my kids, and I felt like I had to choose, and so what I did was instead, I just hired, uh, I hired a trainer, um, initially it was virtually, now it's, now it's in person, um, who every day at 5:30 would show up at the house, And I, I recognize that not everyone, you know, I wasn't able to afford that frankly up until very recently, but you know, like even, you know, everyone has, a lot of us have Pelotons. My suspicion is most of us do the on-demand classes, not the scheduled classes, but actually if you have to do the scheduled classes because you have to show up at four 30 or five 30, it means that is blocking it off. …

AI assessment note: “what I did was instead, I just hired, uh, I hired a trainer”

Q luck, because you've gone from five million to north of six hundred million, I think it is this year, but the interesting thing that Iden pointed out to me was the element of consistent revenue growth, Uh, something that's not attributable to luck, Harley. Uh, but what are the key decisions or unique strategy behind the outstanding consistent revenue growth, do you think, when you look back at the journey?

A So, to be clear, we are first and foremost a product company, and we believe product comes first, and having a great product, revenue follows after that. We don't chase revenue. In fact, if you read our, uh, Toby's letter to shareholders when we filed our IPO, we made it very clear that if you're looking for sort of quick wins, and you're looking for a company that is going to chase revenue, we're probably not the right company. To invest in. We've always been really product focused. And I think the reason is we were, Shopify was the product that we ourselves were looking for when I was trying to sell t-shirts and Toby was trying to sell snowboards. And I think we come to this with a lot of empathy for what entrepreneurs need and require and, and how they, how they sort of think about things. I think part of the reason that you've seen, uh, I think Iden describes the term he uses consistent is we've been very deliberate in the things that we've done. And so we were deliberate in building software that we felt most people needed most can use most of the time. It was very easy to use. It was very Easy to customize, but it was also very scalable. So whether you're starting a store on Shopify at your mom's kitchen table, uh, or you're selling hundreds of millions of dollars of products, which we do in merchants that do that on our platform, you would never have to leave the platfor…

AI assessment note: “By being deliberate on the product side, we've been able to, uh, the revenue has followed”

Q luck, because you've gone from five million to north of six hundred million, I think it is this year, but the interesting thing that Iden pointed out to me was the element of consistent revenue growth, Uh, something that's not attributable to luck, Harley. Uh, but what are the key decisions or unique strategy behind the outstanding consistent revenue growth, do you think, when you look back at the journey?

A So, to be clear, we are first and foremost a product company, and we believe product comes first, and having a great product, revenue follows after that. We don't chase revenue. In fact, if you read our, uh, Toby's letter to shareholders when we filed our IPO, we made it very clear that if you're looking for sort of quick wins, and you're looking for a company that is going to chase revenue, we're probably not the right company. To invest in. We've always been really product focused. And I think the reason is we were, Shopify was the product that we ourselves were looking for when I was trying to sell t-shirts and Toby was trying to sell snowboards. And I think we come to this with a lot of empathy for what entrepreneurs need and require and, and how they, how they sort of think about things. I think part of the reason that you've seen, uh, I think Iden describes the term he uses consistent is we've been very deliberate in the things that we've done. And so we were deliberate in building software that we felt most people needed most can use most of the time. It was very easy to use. It was very Easy to customize, but it was also very scalable. So whether you're starting a store on Shopify at your mom's kitchen table, uh, or you're selling hundreds of millions of dollars of products, which we do in merchants that do that on our platform, you would never have to leave the platfor…

AI assessment note: “we are first and foremost a product company, and we believe product comes first”

Q What's been the biggest challenge you've faced since joining Shopify?

A Figuring out what I'm good at and what I'm not good at. Like I said, when I first joined, I was a bit of a Swiss army knife. I kind of did everything that, that Toby didn't want to do or wasn't interested in doing. And I, as, as time goes on, I had to sort of figure out, okay, well, these are the things I think I'm, I can be world-class at and I can get there, but these things I'm really not good at and hire for that. I think there are some people that are born natural leaders. You sort of have these innate leadership abilities. I don't think anybody is born a natural manager or an innate manager. I think management is something that is really, really tough. It's, it's, it's something that I'm, I'm trying to get really good at, but it's, uh, those leadership management are very different things. And I spent a lot of time working on management. So that's, um, that's been a challenge to me.

AI assessment note: “Figuring out what I'm good at and what I'm not good at.”

Q say, I remember being super nervous. I asked my mother to unplug the home phones in case someone rang. I only had 50 dollars in my bank account, and then I started with Guy Kawasaki. I was super, super nervous, and so I had a chamomile tea beside me. And you bring in the essence That make it so much more familiar for people. Do you see what I mean?

A I mean, you're talking about the craft of storytelling, and I think the craft of storytelling is incredibly important. I mean, you, you, you run a very successful podcast. You sort of, by, by very nature have to be a great storyteller. The relationship that I have with Toby is effectively that in the same. I mean, Toby, I think is probably the greatest product, uh, mine on the planet. I mean, I just, I, I don't say that, um, boastfully. I say that from great, you know, with great insight and great experience working side by side with him for, you know, a third of my life. Um, my job is then to take what he builds and ensure the world knows about it. And the only way the world's gonna, gonna, gonna actually care about it is if I leave These, these breadcrumbs of, of storytelling and narrative. And, you know, if you, if anyone follows me on social media, I talk about Shopify's product a bit, but what I really talk about is our merchant story. Because for me, the way to deeply understand Shopify is to look at Ben Francis in 2013, uh, as a pizza delivery boy in London, uh, in college who decides to start Gymshark and to watch his journey to be one of the most important athletic brands on the planet in 2022. That, and, and the way to do it is not to just talk about his numbers, but I start with what he was doing before I begin to talk about, you know, why he didn't think that the ex…

AI assessment note: “you're talking about the craft of storytelling, and I think the craft of storytelling”

Q you be vulnerable, because I know we speak about the power of vulnerability and all that, which is true, But it's hard, and you don't want to demotivate the team. Can you be vulnerable today? And if so, how can you? And I guess you're kind of advising me here, because I don't want to lose the morale, I don't want to lose the excitement. How do I do it?

A Let me give you one great example that, that really worked well for me. Um, I have had anxiety for the majority of my life. Um, it was undiagnosed. I didn't know what it was, but there was always this thing that, like, I felt deep in my stomach or my gut or my heart, whatever it was. And it manifested itself in a lot of different ways over the years. Um, but eventually, you know, I wanted to understand more about, I wanted to be more self-aware. I wanted to be more self-introspective about, like, what drives me? What are, what are the things I need to work on? And so I began to see a psychologist and I've been seeing a coach for a while. And eventually it became obvious that no, I, but this thing that I have that I'm describing to all these people, it's anxiety. And so the cool part about, um, knowing that is now, now I have all this, now I have a terminology for it. Now I have nomenclature that I can say, like, I can go read books about anxiety. I can talk to people that other people that have come up publicly that said that anxiety. So one, getting, getting that language is really valuable. And then the second thing that I did was I began to talk about both internally at Shopify, but also externally that I have anxiety. And most remarkable thing happened. All these other people who I deeply respect, who I admire and look up to, they came to me and said, Hey, I also have anxie…

AI assessment note: “I began to talk about both internally at Shopify, but also externally that I have anxiety”

Q entrepreneurship, and delivering that to the world, and you've done this with outstanding success. You IPO'd in May, 2015. I'd love to talk about this, and the decision to IPO at that time, when there were potentially fewer tech IPOs than we've seen in the last couple of weeks, for sure. So, what was the process like for you, and why did you decide to do it at that time?

A A couple things. We have very big ambitions here at Shopify. We've always had very big ambitions. We felt that, at the time, the company was ready We felt the team was ready. We felt our product was ready, and there was no reason not to do it. We want to stay a large, independent business for a very long time. We want to build a hundred-year company, and at some point, being a publicly traded business, it makes it easier to be a long-term company, and so it just made sense for us. We had raised three rounds of financing. Our Series C, I believe, was around 2014, raised a hundred million dollar round, and we felt that the company and the team here was just, was just ready for it, and so we went and did it, And honestly, it's been a wonderful experience. Our, our goal then is it still today is not just to be a public company, but really to be a trusted public company. And I think we've done a good job of, of getting, of moving towards that.

AI assessment note: “being a publicly traded business, it makes it easier to be a long-term company”

Q Can I ask what was the biggest learning in either the roadshow leading up to the IPO or the IPO itself? You mentioned the great mentors and the incredible investors that you met. Are there any kind of really tangible learnings that you took from the process, either pre or post?

A There's a couple of things that stick with me about, about that process. I mean, one, one thing is I think we took for granted people's understanding of our business. And so we really had to spend a lot of time. In fact, You may have seen this, but we sort of created a mini documentary of Shopify with the IPO package, whereas most companies, um, you know, yeah, we thought, we thought it was, it was a neat way to do that. Most companies sort of turn their camera on and, and some executive reads a script. We actually created a real documentary to tell the story of Shopify. And I think I took for granted that people understood what we did. And so, you know, there were still people around the IPO point who really weren't sure we are marketplace, how we function. And I may have, you know, when you, when you're so heads down, like we are and we're focused and, Certainly, you know, located in Canada, uh, is, has a lot of benefits, but, but perhaps we're, we're sort of outside the bubble of Silicon Valley, where a lot of these companies are based. It was important that we, we told the story really well. So we, we tried to do that. We also just really just tried to learn as much about that process as we possibly can. And so we stranded ourselves with people that are far smarter than we are. And it was, it was a great process. I enjoyed it.

AI assessment note: “one thing is I think we took for granted people's understanding of our business.”

Q you be vulnerable, because I know we speak about the power of vulnerability and all that, which is true, But it's hard, and you don't want to demotivate the team. Can you be vulnerable today? And if so, how can you? And I guess you're kind of advising me here, because I don't want to lose the morale, I don't want to lose the excitement. How do I do it?

A Let me give you one great example that, that really worked well for me. Um, I have had anxiety for the majority of my life. Um, it was undiagnosed. I didn't know what it was, but there was always this thing that, like, I felt deep in my stomach or my gut or my heart, whatever it was. And it manifested itself in a lot of different ways over the years. Um, but eventually, you know, I wanted to understand more about, I wanted to be more self-aware. I wanted to be more self-introspective about, like, what drives me? What are, what are the things I need to work on? And so I began to see a psychologist and I've been seeing a coach for a while. And eventually it became obvious that no, I, but this thing that I have that I'm describing to all these people, it's anxiety. And so the cool part about, um, knowing that is now, now I have all this, now I have a terminology for it. Now I have nomenclature that I can say, like, I can go read books about anxiety. I can talk to people that other people that have come up publicly that said that anxiety. So one, getting, getting that language is really valuable. And then the second thing that I did was I began to talk about both internally at Shopify, but also externally that I have anxiety. And most remarkable thing happened. All these other people who I deeply respect, who I admire and look up to, they came to me and said, Hey, I also have anxie…

AI assessment note: “I began to talk about both internally at Shopify, but also externally that I have anxiety”

Q We last spoke five years ago on the show. If we speak in five years time, where do you want to be, and what does success in those next five years look like?

A I mean, I always sort of use, you know, my , my, my life's work is sort of the, uh, as the, you know, um, as the context for that, and, and I, I want more people to try their hand in entrepreneurship. I want to change the way that people consider entrepreneurship. I think there's still too many people that find that to be inaccessible. They think it's too expensive, or it's too complicated, and, I think that, um, entrepreneurship is not only the great way to self-actualize, but I think for so many of us, it's the best way to find our ikigai. It's the best way to find our life's work. It's the best way to take what we already love. Let's say you make jewelry at your kitchen table, and you think there's no way anyone may want this. I bet you there is. I think there is people that will want your jewelry, and so that's part of it on the professional side. And on the, on the personal side, um, I want to keep, you know, I want to continue to grow my, My own understanding of who I am and how the world operates. I want to continue to be a great, you know, be a great husband and great father, um, and hopefully inspire others to kind of find their own journey, whatever that might be, and to do it with, with great enthusiasm. Um, I am incredibly optimistic, not just about my own life and about Shopify. I'm optimistic about like the world. I think that we, we live in some of the most inter…

AI assessment note: “that's part of it on the professional side. And on the, on the personal side”

Q along their journey, bluntly, I think, in the way that me and you can. And I think it's maybe, I don't know if it's the proliferation of capital that means they don't need to, whatever it is. Do you agree with the lost art of storytelling? And I guess, what do you think And I can answer this because I have thoughts on it, but like, makes a great story.

A I think what you're talking about is actually, um, I would replace the term story with mission. I think that A lot of founders, um, like you, I'm, I'm very lucky to invest in a bunch of different startups. And, um, obviously, you know, the, the, the obvious things are you look for grit, you look for vision, you look for, you know, someone who's just gonna grind and someone who is so deeply passionate about solving a problem. But I think the company is that, that I, I think I've done really well is they have a deep understanding of what their mission is and you can call it story. Um, but, but I think the two are pretty much the same. Um, You know, from a very early stage, uh, you know, Zuck and, and, and Facebook or Meta, they were very clear on what their mission was. You may not agree with it, but their mission was to connect the world. Um, and you know, Google had a very clear mission. Uh, it, it was to organize the world's information. I mean, later on it was, you know, do no evil or whatever it was, but initially it was very obvious what the purpose of Google was. And I think if you look at these iconic companies, you, you have those. Um, so. I don't think there is a way to build, um, a hundred year business, which is what we're trying to do. We're, you know, 15 years in now, uh, or to have a company that fundamentally changes the way things are done if you don't have a ver…

AI assessment note: “I would replace the term story with mission”

Q everyone's like, oh, where is he now? And you're like, oof, I don't know. Um, my point being, like, that's my big insecurity and fear. When you look today, man, respectfully, Shopify is a vast company, and you're the president. Like, what insecurities do you have today? And I guess, you know, when you sit on your own in the armchair, what do you like? I'm really insecure about this.

A Um, I read this thing a couple days ago, which I loved. I'm going to try to pull it up here for a second, because I want to get it, I want to get it exactly right. It goes like this. Um, the most important law of ecology is this. So there's, I think there's four laws of ecology, and this, this, this writer says this is the most important law. For an organism to survive, the rate of learning must be equal to or greater to, or excuse me, must be equal to or greater than the rate of change happening around them. With the rate of change escalating, we must learn faster, learn better, and learn more. I think a lot about that. Um, I, I, that's, those are, that's, that's a better way to put it. That's a better sequence of words than I've ever used, which is why I wanted, I wanted to quote that directly. But that, that's what I'm insecure about. Um, I'm insecure about the fact that Shopify has, I think, one of the most incredible opportunities of any company that's ever been built to truly change the way entrepreneurship, business, independence, success is created. And again, not everyone's going to want to take their company public, uh, like, you know, Figs or Allbirds on Shopify. Some, you know, set up stores on Shopify and businesses simply because they want to put food on their table, like my grandfather, or they want to afford, you know, ballet lessons or hockey lessons or, you kn…

AI assessment note: “that's what I'm insecure about. Um, I'm insecure about the fact that Shopify has”

Q along their journey, bluntly, I think, in the way that me and you can. And I think it's maybe, I don't know if it's the proliferation of capital that means they don't need to, whatever it is. Do you agree with the lost art of storytelling? And I guess, what do you think And I can answer this because I have thoughts on it, but like, makes a great story.

A I think what you're talking about is actually, um, I would replace the term story with mission. I think that A lot of founders, um, like you, I'm, I'm very lucky to invest in a bunch of different startups. And, um, obviously, you know, the, the, the obvious things are you look for grit, you look for vision, you look for, you know, someone who's just gonna grind and someone who is so deeply passionate about solving a problem. But I think the company is that, that I, I think I've done really well is they have a deep understanding of what their mission is and you can call it story. Um, but, but I think the two are pretty much the same. Um, You know, from a very early stage, uh, you know, Zuck and, and, and Facebook or Meta, they were very clear on what their mission was. You may not agree with it, but their mission was to connect the world. Um, and you know, Google had a very clear mission. Uh, it, it was to organize the world's information. I mean, later on it was, you know, do no evil or whatever it was, but initially it was very obvious what the purpose of Google was. And I think if you look at these iconic companies, you, you have those. Um, so. I don't think there is a way to build, um, a hundred year business, which is what we're trying to do. We're, you know, 15 years in now, uh, or to have a company that fundamentally changes the way things are done if you don't have a ver…

AI assessment note: “the way that the mission is articulated to the world is through storytelling.”

Q You know, you said there about being team Lindsay and being team Harley. Bluntly, I think the best entrepreneurs have Really selfish. Um, and I have been really selfish over my life because I haven't had anyone else. And now I'm worried that I will have to be less selfish because I've got team power as well. So how should I think about reverting to the mean and that concern?

A You know, uh, you want to go fast, go alone. You want to go far, go together. And I think, you know, I want to go far in my relationship. I believe that part of my ability to Um, operate at this, I don't know, the, the beats per minute of my life is very high. With Shopify, with my personal life, having two, I have a two-year-old and a five-year-old. Zoe is two, and, and Bailey is five years old. The only, you know, the only way I can do this is if I have a really strong foundation and that strong foundation comes from my family. Uh, it comes from my marriage to Lindsay. It comes from my relationship to like my, my, my closest friends, my dynamic with my, my colleagues and, and, and Toby. Um, and so I guard for that. And, and, and I, I think you need to decide, uh, everyone needs to decide whether or not they want to run their marriage, like they run their business. Um, and I'm not sure that's always the same thing. I do think actually there are a lot of similarities to it. You know, we talked about empathy earlier or authenticity or vulnerability. I mean, there's some things that are just universal things that, um, I think humans need to, need to adopt. Cause I think you get better results with it. Um, but I think, you know, like, let's say you do Lindsay and I have a ritual. We have, we, we have date night and date night has become a little bit strange during COVID, but we've…

AI assessment note: “You want to go fast, go alone. You want to go far, go together.”

Q Can I ask, what do you, what do you think makes a trusted public company? Is it a lack of volatility? Is it a united team? Is it a fantastic culture that's embodied in the brand? What is it for you that embodies that trusted public company to the wider market?

A Yeah, I think it's similar than that. I think it's, you do what you say. And we've now, we just announced our last earnings for QN, 2017 past Tuesday. And so we've been public now for eight quarters. And I think the, I think really trust is built on consistency and doing what we say time and time again. Um, we're going to make mistakes and I think all companies do that. We learn from those mistakes and, and there's going to be things that don't always work here, but I think we're candid. I think we're quite transparent and we do what we say. And so that I think is, is really the key. But, you know, myself and Toby, we've never ran a publicly traded company before. Even our CFO, who has a lot of experience as a CFO, he's never really ran a public company either. So we, we tried to really learn as much about the process as we possibly can. We, we had some great mentors and great advisors, people that had either gone public or who understood the capital markets and the IPO process. But it's been a really, it was a great experience. And I don't know, I have to say the roadshow for me was one of the most interesting and exciting two weeks probably of my life. I got to Fly around the world and meet incredible investors and great, really smart people. And I got to tell the story that is my favorite story, which is that of Shopify.

AI assessment note: “I think really trust is built on consistency and doing what we say”

Q You mentioned that kind of growing at the same rate that Shopify does. That's really fucking hard. Um, my question to you is, what does your coach say and how do you approach that then? Because it is such a challenging thing to grapple with. How do you actually approach that and what does your coach and support system say to help you think through that?

A I heard this thing, uh, that entrepreneurship is, is a personal growth, uh, journey disguised as a business. Um, that's kind of what Shopify is for me. Shopify for me is This incredible company that also allows me to, to, to, to, to grow at this, at this, at this rate. Um, look, I, I think part of that journey, I've been at Shopify now is it's like my, my Shopify bar mitzvah. I've been in Shopify now for 13 years. Um, I'm 38 years old. So about a third of my life has been spent at this company. And I, I, I don't take that for granted. It's, it's, I'm, I'm truly like, I feel really, really grateful for that. Um, But part of it is not necessarily doing everything. And part of it is knowing what I'm really, really good at and honing that skill. And I think actually this is where a lot of larger companies get this wrong. I think, um, Toby uses this great analogy of like a river stone. You take this like beautiful spiky stone. And if you put it in the river over years and decades and hundreds of years, it becomes this kind of smooth and evenly, you know, uh, non spiky river stone. We don't want to create Riverstones at Shopify. I don't want to be a Riverstone. I want to be spiky in certain areas, but in order to be spiky in certain areas, that means that I'm not necessarily going to be great at everything. And so having that, you know, that awareness to say, look, this is not like, …

AI assessment note: “part of it is not necessarily doing everything. And part of it is knowing”

Q You know, you said there about being team Lindsay and being team Harley. Bluntly, I think the best entrepreneurs have Really selfish. Um, and I have been really selfish over my life because I haven't had anyone else. And now I'm worried that I will have to be less selfish because I've got team power as well. So how should I think about reverting to the mean and that concern?

A You know, uh, you want to go fast, go alone. You want to go far, go together. And I think, you know, I want to go far in my relationship. I believe that part of my ability to Um, operate at this, I don't know, the, the beats per minute of my life is very high. With Shopify, with my personal life, having two, I have a two-year-old and a five-year-old. Zoe is two, and, and Bailey is five years old. The only, you know, the only way I can do this is if I have a really strong foundation and that strong foundation comes from my family. Uh, it comes from my marriage to Lindsay. It comes from my relationship to like my, my, my closest friends, my dynamic with my, my colleagues and, and, and Toby. Um, and so I guard for that. And, and, and I, I think you need to decide, uh, everyone needs to decide whether or not they want to run their marriage, like they run their business. Um, and I'm not sure that's always the same thing. I do think actually there are a lot of similarities to it. You know, we talked about empathy earlier or authenticity or vulnerability. I mean, there's some things that are just universal things that, um, I think humans need to, need to adopt. Cause I think you get better results with it. Um, but I think, you know, like, let's say you do Lindsay and I have a ritual. We have, we, we have date night and date night has become a little bit strange during COVID, but we've…

AI assessment note: “You want to go fast, go alone. You want to go far, go together.”

Q and I promised myself I'd never let my family be in that position again. That's why I work my fucking ass off. Um, you mentioned they're losing everything. I, I, I hope it's okay for me to ask, how, how did you deal with that, one, and then two, how did it impact you, do you think? Like, for me, it made me Just unwaveringly and unhealthily obsessive about winning.

A If you just look at COVID, for example, it was a great example. It was a great opportunity to see this in, in, in real time. COVID hits pretty much the whole world, February, March, April, 20, 20. And there was, you pretty much saw one of two reactions from people, from businesses, from, from corporations, from, um, associations, just generally there was, there was, there were two ways that people Reacted. One way was the sense of resistance that this is bad. I can't wait to go back to the, the old way. And there was this other group of people that were incredibly resilient that basically, you know, they saw this tidal wave and they took their surfboard and surf and surfed and, and, and they saw some opportunity in what was frankly, uh, you know, a global devastation. And I, I think that's kind of how most people deal with, with real big setbacks. Um, they either go to the couch and put their blanket over their head or they get up and they try to figure it out. And, um, I, the reason that I, the reason I've committed my entire life, both professionally with Shopify, but also personally to entrepreneurship is because I think entrepreneurship is this incredible tool to dealing with incredible setback. Um, if you lose your job, You can use entrepreneurship to supplement your income. If your dad goes away and your mom and sisters don't have no money, you can use entrepreneurship to…

AI assessment note: “my version of success when I was 17 and sort of the world ended for my family was survival”

Q Can I ask, what do you, what do you think makes a trusted public company? Is it a lack of volatility? Is it a united team? Is it a fantastic culture that's embodied in the brand? What is it for you that embodies that trusted public company to the wider market?

A Yeah, I think it's similar than that. I think it's, you do what you say. And we've now, we just announced our last earnings for QN, 2017 past Tuesday. And so we've been public now for eight quarters. And I think the, I think really trust is built on consistency and doing what we say time and time again. Um, we're going to make mistakes and I think all companies do that. We learn from those mistakes and, and there's going to be things that don't always work here, but I think we're candid. I think we're quite transparent and we do what we say. And so that I think is, is really the key. But, you know, myself and Toby, we've never ran a publicly traded company before. Even our CFO, who has a lot of experience as a CFO, he's never really ran a public company either. So we, we tried to really learn as much about the process as we possibly can. We, we had some great mentors and great advisors, people that had either gone public or who understood the capital markets and the IPO process. But it's been a really, it was a great experience. And I don't know, I have to say the roadshow for me was one of the most interesting and exciting two weeks probably of my life. I got to Fly around the world and meet incredible investors and great, really smart people. And I got to tell the story that is my favorite story, which is that of Shopify.

AI assessment note: “trust is built on consistency and doing what we say time and time again.”

Q You mentioned it potentially not being the end of brick and mortar like many suggest. A lot of VCs that I speak to suggest that we're going to see retail transition from a transactional location to a experience that consumers Can enjoy. What's your thoughts on that and the need for retail to make the transition from transaction to experience?

A I think physical retail is probably going through its, its largest shift. And part of it is that there's a couple of big macro trends happening here. So one macro trend, I think that that's, that's driving it is this idea of direct to consumer or disintermediation is another way to put it. So I ride a boosted board most days to work in the summertime, which is this amazing motorized skateboard from my home to, to the office. Um, If I were to walk into a big department store or a big electronic store that sells a ton of different brands, and I were to ask them, tell me about the Boosted Board. Tell me about this new Boosted Board too that just came out. What's the range of it? You know, what's the battery life of it? How fast does it go? I would probably get some sort of weird look from the salesperson because I'm not actually sure that that person knows more about the board than I do as a very typical consumer. When I go to BoostedBoard.com, which is an online store on Shopify, I A little chat box pops up in the bottom right corner, and I can ask all these questions. I can get answers in real time from the people that are making the product, that care a lot about the product, that are, that have a real understanding about the R and D behind this new boost or two that has just come out. So from a consumer perspective, I, and I think many others are now, a lot of us prefer to go …

AI assessment note: “prefer to go direct to consumer because I get a better experience as a consumer”