Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein

Ilana Golan: [00:00:00] [00:01:00] look, you started entrepreneurship when you literally had no choice. You did a bit as a kid. We'll talk about that too. But you leap to entrepreneurship in a very, very dark place personally and for the family. Can you share what happened, Harley? Harley Finklestein: So as you said, you know, as a kid, I was always entrepreneurial. I always had, you know, I guess what would now be called side hustles. When I was 13 years old, I started a little DJ company. I was always tinkering and toying with little businesses when I was a kid, but it was only when I was 17, I moved from South Florida. where I was living to Canada to go to McGill University. And within about a month into school or so, my parents got into some real financial hardship. My dad was no longer around. He got into some [00:02:00] trouble, and I didn't really know what to do. I felt this wave of angst, this wave of uncertainty come over me. I have two much younger sisters that were living down back in Florida with my mom. And things were, things were about as dark as they could have gotten. And I decided at that point that in a similar vein to when I was younger, and I wanted to be a DJ and nobody would hire me. I started my own DJ company and hired myself. I once again used entrepreneurship when I was 17 to solve this problem, which was not passion or interest or novelty like being a DJ. It was desperation. I had to pay my tuition. I had to pay for my rent. I had to support my mom and younger sisters. And I started a little t shirt business to make t shirts for universities in 2001 and changed my life. It changed my life from a financial perspective. It changed my life from a place of responsibility, helping my mom and sisters. But [00:03:00] entrepreneurship was then and is today still the tool that I take out most often, most readily when I'm trying to solve a problem. It's not to say everyone does it that way, but in my darkest times, And also frankly, even my happiest times, maybe we'll talk about, I just wrote a kid's book for my daughters about entrepreneurship. I use this tool called entrepreneurship to solve problems. And it has been the most effective tool, the most effective way for me to resolve something that is deeply concerning or deeply of interest throughout my entire life. Ilana Golan: Wow, I never thought of entrepreneurship as a problem solving, which I guess it is. But I want you to take me back in time then to this 14 year old that decides to be a DJ. How did you even start? Harley Finklestein: Actually, I'm going to show you something I've never showed anyone. Ilana Golan: I like that. I always do. Harley Finklestein: This was actually my very first business card. Ah! And if you can see it, it says, [00:04:00] Fresh Vibe Entertainments. The reason I have this is because my mother recently founded and gave it to me. But this business card is dramatic to me. It is incredibly meaningful. Why? Because when I came home, I was 13. I'm Jewish. I went to a lot of bar mitzvahs and I thought the DJs were just so cool. They were so interesting. They would take a party that was sitting down kind of lame and, and quiet eating their dinner. I A minute later, they were doing the conga line. I thought that was just so interesting. And so I applied to a bunch of DJ companies and nobody would hire me. One, because I wasn't, I didn't know how to DJ. And two, I looked like I was eight years old or something like that. I've always been sort of shorter than my peers, smaller than my peers. So, yeah. I had this deep desire and so my mom and dad, who didn't have a lot of money, encouraged me throughout my entire life by making this, these silly business cards that were probably made on a simple home computer printer. They would make me these cards and they would validate this [00:05:00] idea that if you want to do something, go create it yourself. And in this case, it was go create your own DJ company and hire yourself. And I ended up DJing about 500 bar mitzvahs and parties between the ages of 13 and probably around 19 or 20 years old. And I loved it. I loved every minute of it. I loved making money. I loved the logistics of it. I loved the performance of it. But ultimately, when I zoom out from those moments, what I then realized was that entrepreneurship was my life's work. It was how I want to spend my time. It's my craft. And you mentioned in the opening that Shopify has grown. We're now a 100 billion company. The entire mission of even Shopify is entrepreneurship. How do you invite more people into this thing called entrepreneurship who otherwise may not have done so? Either they were scared or they didn't have the know how or they thought it'd be very expensive. All of those things are no longer the case. Today, if you have an idea in the shower, you can take that idea and turn it into a small [00:06:00] business. And if you're lucky and you're good and you're adding value, that may turn into a multi billion dollar company. And so that's my roots in entrepreneurship and why it's so meaningful to me. Ilana Golan: That is so incredible because first of all, the fact that they even thought of creating those cards, there wasn't Moo cards or whatever, you know, the typical card creators, right? Harley Finklestein: There wasn't any of those easy to use websites. In fact, there weren't really any e commerce then, but the card itself is less about, The card is more about what it meant to me. It meant that they believed I could do this. They gave me the audacity to believe I can do it. And again, the card is not very fancy. And it just says Fresh Vibe Entertainment, says my name and my best friend's name on there, who is my business partner. But this was Ilana Golan: But it made it real. Harley Finklestein: The beginnings of this. It made it real. Ilana Golan: So to me, first of all, that means that your parents Were a big driver, they understood entrepreneurship when it wasn't. A cool thing yet. [00:07:00] So take us a little bit to where it's college because you're also learning something that is completely not what you do today, but take us a little bit there. Harley Finklestein: So as I mentioned, I moved to Montreal when I was 17 to go to McGill University. Mom and dad needed help financially. Dad was not around anymore. I started selling t shirts because I needed a way to make money. And I didn't necessarily want to do a reduced course load. I wanted to make money concurrently when I was in school. And so there weren't a lot of jobs out there that would allow a student to Take a full course load, but the cool part of entrepreneurship is you as the entrepreneur, as you're building your business, you get to mold the business around your particular needs, your particular schedule, your particular set of circumstances. And so a friend of mine was on student council at McGill University. And told me that McGill, I think the original quote was McGill spends 25, 000 a year on t shirts, promotional t shirts. So faculty of science or faculty of arts or [00:08:00] orientation or any of that stuff that you see in a university bookstore on campus. And I knew that Montreal historically had a very prominent, uh, Shmonta business, clothing industry, you have companies like American Apparel and Buffalo Jeans and Paris Succo and Aldo and Browns. A lot of big companies that are now global companies were built, Gildan for example, were all built here in Montreal and so I knew that not knowing anything about the t shirt business that I probably would be able to find people here. in town who would either help me with screen printing or who I can buy blank t shirts from. And it wasn't this big, passionate, I need to be in the t shirt industry. I loved it. It wasn't about t shirts at all. It was, I thought of an opportunity that McGill buys t shirts. I was a McGill student. Most of the t shirts that I had worn that McGill had given me in my first couple of weeks of school were not very good. They were ill fitting. They had large rib collars, which are not fashionable. [00:09:00] They were all kind of boxy. The logos didn't look very nice. It was obvious to me that I could do this better if I was given the opportunity to do so. And so I ended up going to meet the student council of McGill and telling them I'm a student here. I told them I have a t shirt business. I didn't. Fake it till you make it. But I told them I had a t shirt business. And I told them that as a student of McGill, I think I have a lot more empathy and a lot more understanding of what other students may need. And I would really be grateful if they would give me a test order. And I remember they gave me a test order. And you know, I always sort of believe this idea of like, just always over deliver. Everything you do over deliver. And so I think their test order was for like 100 t shirts and I brought in 120 t shirts. And I gave my cell phone number because I knew that all these other big companies, there's no way the sales rep was going to give them their cell phone number. But it was my business. I was the secretary and the assistant and the CEO and the head of production. I was the Jack, I was everything. So I gave them my cell phone number and said, if there's [00:10:00] any problems at all, give me a shout. And that first t shorter went off without a hitch. It was fantastic. And then I began to realize that I can use the same model. At other universities where I would go in, I mostly focus on Canada, but I had friends at every university across Canada at that point, or at least I knew someone at each university, and I would just call and say, introduce me, and they'd introduce me and I'd go in and I'd always over deliver, and the best part about it was when I was competing against these larger businesses that were selling t shirts, they would go in with a catalog, papers of, you know, you can choose this t shirt, this, I would go in with actual t working samples, physically printed samples. So instead of saying, which GSM count, which weight of t shirt do you want? Do you want a poly cotton or do you want just a cotton? Do you want something a little more stretchy? Something a little bit more vintage looking? I would actually bring the t shirts themselves in and so rather than having to select them using paper, they can select them with the physical [00:11:00] samples. And by the end of university, uh, this is 2005, dozens and dozens of universities across the country were buying t shirts from me and I was able to build a real business doing it. It was remarkable. Ilana Golan: And again, this one didn't start with a passion. It started because your back was against the wall, which I think is also important to understand. Sometimes it is really great to follow your passion, but sometimes you also need to do things because this is what you need right now. Harley Finklestein: You mentioned earlier that my parents with the business card brought entrepreneurship to me. It wasn't that my parents were necessarily entrepreneurs or entrepreneurial. It's that my dad's an immigrant. My dad came from Eastern Europe to Canada in the 50s. My grandparents, his parents were Holocaust survivors. When they came to Canada, they were very poor. They didn't speak the language. They had no money. So the only job that my My paternal grandfather was able to have in Canada, the new world in his nomenclature, was he was able to start a little business. [00:12:00] He was an egg merchant. He sold eggs at a local farmer's market. He didn't call it entrepreneurship. He called it survival. He knew that he wanted to put food on the table or had to put food on the table, had to put a roof over the heads of my father and my grandmother and my father's siblings. And so entrepreneurship wasn't this, what it is today, which is follow your dreams, build something with great desire and passion, something with great meaning. He was passionate about surviving, not passionate about the entrepreneurial venture themselves. And so I think the fortunate opportunity that I had was my parents. didn't look at entrepreneurship as a luxury, as this creative outlet, they viewed it as a way to solve problems because that's what they saw their parents using it for as well. Ilana Golan: And like you said, when you're an entrepreneur, you wear a gazillion hats, speaking of hats, you wear so many hats and it is about just solving problems. I see something, I go all in, I see something, [00:13:00] I go all in. But it's never been easier to start a business, which I want to talk about as well in a second. But talk to us a little bit about from selling shirts, how did you join Shopify and how did that all happen? Harley Finklestein: So I finished undergrad college and a mentor of mine, I've always had really great mentors in my life since I was a kid. The group of mentors each has one, I don't know, call it a superpower that I really want to copy or really want to emulate. What I realized was there is no one person that exists on the planet who I want to copy the entirety of them. But I like one aspect of what they do. I like the way they parent their great mom or dads or their great spouses. They have a great relationship with their wife or husband or their life partner. They're in incredible shape. They get to do crazy athletic challenges. Or the way that they articulate themselves is so interesting and so compelling. So I had a mentor of mine who convinced me that [00:14:00] while the t shirt business was a good business, that that wasn't ever going to lead to having a large enough impact. And the t shirt business was a good business, but It wasn't going to change an industry. It wasn't going to allow me to build something that I really wanted to build, which is something that is multi generational and incredible. And he convinced me to apply to law school. The idea was. I should apply to law school not to become a lawyer, but rather to become a better entrepreneur. And he was a lawyer and he thought that law school would be like finishing school for me as an entrepreneur. I'd learn how to write and think and articulate myself and do all these things that maybe I didn't really have at that particular time when I was in college. And he happened to be teaching law, law school at the University of Ottawa. And so I applied to one law school. It was just the University of Ottawa. I applied there, took the LSAT, fortunately got in. And I moved to Ottawa in 2005 to begin law school. And I realized when I got there that this t shirt business was never going to [00:15:00] survive because ultimately it requires me going and meeting these student council people that were buying t shirts face to face. My entire unfair advantage was I was selling t shirts to students as a student myself. And the business model just kind of broke if I had to go to class and in law school you actually have to attend class unlike undergraduate or college where you can just show up for the exams. So I moved to Ottawa in 2005 and wanted to meet people. You know, I wasn't really Becoming friends with people in law school, they were very serious. They wanted to be lawyers and they were very studious. And I was an entrepreneur. I was a lot more interested in the value extraction from the curriculum of law school. I didn't care about doing well on the exam. I cared about selfishly, you know, it's like an exchange. I'm giving the law school 10, 000 or 15, 000 per year in tuition. In return, I'm demanding 15, 000 worth of value. And so I didn't get caught up in grades. An exam is [00:16:00] because I wasn't why I was there. I was there to extract value, to gain new skills. But as we've talked about ever since I was a kid, the entrepreneur community was always my tribe, my people, my closest friends have always been entrepreneurs. It's still are to this day. And I asked where the entrepreneurs hung out in Ottawa. And I was directed to a coffee shop, and it was a group of entrepreneurs that got together every Friday evening to exchange war stories, and talk about best practices, and share tips and tricks, and they called themselves the Fresh Founders. And I joined this small group of quote unquote Fresh Founders, and one of those Fresh Founders was this brilliant programmer named Toby, who just moved Two years earlier, from Germany to Canada. When he got to Canada, he couldn't get a job because he was a new immigrant, didn't have his working papers. But he knew he could start a business. And he began to sell snowboards on the internet. And he wrote a piece of code on his own, he's a coder, to sell these snowboards on the internet. [00:17:00] And very quickly realized that while these snowboards were a good idea, the code that he'd written to sell the snowboards was a great idea. And that more people may want to use his software to sell their own products. And I was one of those people. I became one of the first merchants, the first customers, the first people to use what is now Shopify. I moved from a wholesale t shirt business to a promotional t shirt business with logos and licenses, Batman, Spider Man, really cool licenses. And I set up an online store on Shopify in 2006. And that was my introduction to Shopify. And after I finished school, I called Toby and asked him if I could join him. A small group of engineers, mostly engineers, and help them build the business. And that was 15 years ago. Ilana Golan: Incredible. So it's almost a third of your life, but who's counting, Harley? Harley Finklestein: More than a third of my life, yeah, crazy. Ilana Golan: But early stage, when you start something, there's going to be a trillion challenges, especially because how fast Shopify grew. Can you [00:18:00] share a little bit of the beginning, some hard moments that you all needed to confront? Harley Finklestein: Well, two things. This was the case then, it's still the case today. In many ways, businesses are a living thing, a living creature. And so, think about biology. Think about out in nature. There's something called the law of ecology, and there's four laws of ecology. And one of those laws of ecology says that for a species to survive in any environment, the species needs to evolve faster than the rate of change of the environment changing. Ilana Golan: Darwin in the making, exactly. That's exactly right. Harley Finklestein: I think companies are like that also, I think when you are early at a company, whether you're the first person in the room or the 10th or the 10, 000th person in the room, every company has a particular beats per minute or a cadence, and that cadence is often a cadence of change, and I think to be successful in any organization, again, early or even later stage, you have to figure [00:19:00] out what the cadence of change is and make sure you are adapting to it. rapidly enough to a degree that is equal to or greater than the change of the organization itself. That's the first thing. Second thing is, I think it's really important, especially in the early days, to act as a bit of Swiss army knife to say, not this is my job. This is what I'm going to do, but rather let me look at the. buffet of problems here. And let me figure out what is the most important problem to solve. And I'll do that first. And then I'll go look at the next buffet. What's the next problem solving? And I'll go focus on that. So the early days of Shopify, we didn't have a CFO. We didn't have a chief marketing officer. We didn't have a head of sales. We didn't have very many people. It was a small handful of people. And so what I tried to do as much as possible is figure out what The teams, very small team needed from me, most importantly, and focus on that. And I remember in 2010, we raised our first round of financing and we were starting to get some term sheets from some great [00:20:00] venture capitalists in the U. S. and there were terms there. They wanted to know what our MRR was and what our CAC to LTV ratio was. Some of them had a liquidation preference and there are some that did not. At that point, you have no choice but to learn it. I had an incredible clip because in those early days, back to the law of ecology, the rate of change of the business of the company is so quickly that in order for you to keep up and be valuable, you just have to continue to grow so rapidly. And if you do, You then requalify for the next phase. And if you don't, you don't deserve to be the next phase. And I always thought of it like that. But even in terms of today, we have millions of stores on Shopify. We just crossed the 1 trillion with a T, the 1 trillion mark of total GMV, of total sales on our platform, which is unbelievable. But in those early days, It was e commerce for small businesses. And now we help power commerce in physical retail stores, on social media, on marketplaces. We have merchants in 175 countries. [00:21:00] We have very large merchants like Mattel and Procter Gamble using us. So, Even from a product perspective, the product of Shopify has changed so much that we can no longer simply just be e commerce for small businesses. Today, we have to be commerce for everyone. And that changes the way you make decisions. It changed the way you think about the future. It changes the business model of the company. But the one thing that has not changed from a tiny little company in Ottawa, Canada, to a hundred billion dollar global retail company, Commerce platform is that the people that work at Shopify to be successful. We expect that they requalify every year for their job based on what the company requires of them. And what the famous, what got you here will get you to where you want to go. That is true. What you did last year was great for last year. It is not good enough for this year. Ilana Golan: I'm hearing a few things that I think I want to make sure the listeners are really, really hearing. Because. You became that person [00:22:00] that is there for whatever is needed. If there's a problem with finance, we don't know you're in. If there's a problem with operations, you're in. And it sounds like this is part of the reason why you zoomed up the ladder and eventually became COO. We'll talk about that. But that's probably one of the reasons why you became because you're right. Otherwise, you lose relevant as a speed that we've never seen before, especially now. Like, I feel things are moving so fast. Harley Finklestein: The pace of company building. You can't see it, but it's just on the side of my desk here. I have the original screen print from Gymshark. Gymshark is a merchant on Shopify. Ben Francis started that company in 2012. Ten years after he started in 2022, Gymshark was a billion dollar company competing with Nike. In the history of the world, we have never seen acceleration and pace of growth of company building that we're seeing right now. Never before would a company go from [00:23:00] zero in a college dorm in the UK to a billion dollar behemoth competing with Nike in a span of one single decade. So the amazing part is that if you understand this and If you understand what you need to grow from an education perspective, from a philosophy perspective, from a hustle perspective, the energy that's required, you can build remarkable things. And those things weren't possible for some random person to build 20, 30, 50, 500 years ago. 500 years ago, the people that were building the biggest companies had a lot of money. They had a lot of connections. They had incredible backgrounds and they were someone's grandson or niece or something. There was something in their family history that allowed them to have this incredible, not easy, but an easier way to grow into scale. That is not the case today. Entrepreneurship as much of a meritocracy is, [00:24:00] it's not a perfect meritocracy. There are still people that don't have access to the internet around the world. So obviously there, there are some people that are starting from further back in the race as a whole, specifically in the developed world. The amount of opportunity that someone has right now is unlike anything we've ever seen. And that's what keeps me so optimistic about the future of entrepreneurship. Ilana Golan: And I think you're right. And I think that the listeners, again, not everybody's built for entrepreneurship, but it's never been easier. It's never been cheaper. It's accessible. It's accessible to anyone that is willing to continue when most others stop. Harley Finklestein: You asked specifically some of the things that that helped me climb. Let me be very specific. Couple things. There is a meme or a narrative right now on this thing called Founder Mode. Brian Chesky, who's the founder and CEO of Airbnb, said it on stage a few months ago and there's been a bunch of blog posts and articles written about Founder Mode. Founder Mode is very simple. [00:25:00] It just means you have to be in the details and you don't have to be a founder to be in the details, but as a leader, I think the best way to operate today is in founder mode when I am working on something, a project. I expect the people I'm working with to know a lot about it, but I often will go five levels deeper into the details. When we're doing an earnings call, for example, I know there are certain metrics I want to talk about, there's a certain narrative. I need to write my own script. I need to ensure that it's Every word choice I use is specifically geared towards the message, the audience, the timing of, of when we're talking about it. Toby still writes code when he's working on an important project. He'll still go in and write code to make sure that it's done a particular way. So one is I think getting into the weeds is really important at any stage of company. The second is, I have a default to action. One of my superpowers is being exothermic. I try to add energy to things. But when I see a problem, my first instinct is to try to solve it. That works very well in [00:26:00] my business. That works less well in my marriage. I mean that. My wife and I have a great relationship. We've been I've said this publicly before, but since getting married 11 years ago, we've been seeing a couples therapist just to kind of help us make sure that we're communicating properly. And I think when she comes to me with a problem, her name is Lindsay. When Lindsay comes to me with a problem, my first instinct is to try to solve the problem. Doesn't work great. Because sometimes she just wants me to commiserate, be empathetic, to just be sympathetic, to say, yeah, that sucks. I don't have that. And that's not great in, in a marriage perspective, but in a business perspective, default to action really, really does help. The other thing that I think is super helpful is, I mentioned this term earlier, but I'm really an eternal optimist. I think getting things done is important, done is better than perfect, but sloppiness is not acceptable. But when I see a problem, I try to figure out what is the best version of the solution for that. I also think that, The people you work with on a day to day [00:27:00] basis, one metaphor that I really love, we use it at Shopify a lot, is the trust battery. This idea that when you begin to work with someone for the very first time, you started a 50 percent trust battery. And over time, with consistency, and them doing what they say they're going to do, you doing what you say you're going to do, the trust battery goes up. And eventually it gets to 100%. And when it gets to 100%, that's when you're cruising. That's when you can really jive with someone. You can work so well together because you can rely on them. And that's really important. The flip side is, eventually, if it doesn't go well, the trust battery gets lower, and lower, and lower. And like an old cell phone that hasn't been charged in two years, eventually, It could never be recharged. And so thinking about the metaphor directionally of, do I have a full trust battery or not is a good litmus test to ask. And the last thing I'll say is I mentioned my wife, our family motto with my wife and my children is how you do anything is how you [00:28:00] do everything. And to me, that's just a proxy for. intentionality. I think that I put as much effort into editing those quarterly earning scripts or closing a large partnership as I do into writing an email to one of our merchants to say thank you. I think this idea of being super intense, you don't have to do everything, but things you do do that are important, being really intentional about. The level of effort and energy you put into it really, really matters, and people see that. People, I don't wear a suit every day, I wear a black t shirt, but the person who makes my black t shirts, his name is James Purse. James Purse thinks as much about black t shirts as Elon Musk thinks about rockets, and thinks about lithium ion batteries. They're these people that get so interested in these challenging things. I love that, that inspires me. Ilana Golan: Oh my God, I love these nuggets. I was totally writing this down because I never thought about it as a trust battery, but it's so true and it's so accurate. Harley Finklestein: You'll never really know exactly what number you're [00:29:00] at. You're never going to say I'm at 87 percent or 52, but you can sort of understand directionally. Yeah, the trust battery with this person is going up or it's going down. And if it's going down, it better go up pretty soon. Otherwise, you're going to have a problem. Ilana Golan: And the other thing, Harley, that I believe from everything that I've seen with Shopify through the years, culture has also been a big play for you, right? Aligning with the mission, believing in a mission, aligning the people and the culture to the mission. Can you talk a little bit about that, Harley? Harley Finklestein: Well, first of all, I think culture has a lot of definitions. The best way I have found to gauge culture is, what do people do when no one's watching? It's a very simple heuristic, but it speaks volumes. When no one is watching, how does someone on your team in your company operate? And I think when you match being really good at hiring the right people and giving them a really great mission, you get [00:30:00] incredible results. Our mission is very simple. We want to create more entrepreneurship, full stop. And this idea of inviting more people into entrepreneurship means that the people that use Shopify. They can find their own versions of success. For Ben Francis, from Gymshark, like I mentioned earlier, his definition was to change The athletic apparel industry, and he did. Gymshark is incredible. They can be one of the biggest companies on the planet. In the case of Trina, who's the founder of Figs, they completely disrupted the modern day hospital scrub industry. If you walk into any hospital now, you see most doctors and nurses and frontline workers wearing certain scrubs, and you see a few, some percentage, wearing Figs. And the ones wearing Figs look better, feel better. So that was Trina's definition of success. But for a lot of others. Their definition of success is not disrupting the industry. It's not to become a billionaire. It's not to take their company public. It's just like my grandfather. It's to put food [00:31:00] on their table. It's to create a better life for their children and grandchildren. It's to afford ballet lessons, or football equipment, or whatever their children and their families require of them. And so what we try to do at Shopify is, because we're a company focused on entrepreneurs, We try to hire entrepreneurs for founders by founders is sort of the thing I love to talk about. This idea that if you had been affected by entrepreneurship in whatever way, in most positive ways possible. Come help us spread more of that around the world. Bring in more people into this idea of entrepreneurship. And I think when you do it, when you marry people that care about something with a company that cares about something quite similar, where the Venn diagrams begin to overlap. You get an incredible culture. You get a culture of people that are obsessed with the people they serve, that are curious about their stories. I want to learn more about them. And I'm really proud of the culture. We built the chopper, but 8, 000 [00:32:00] people at the company today. I'm very proud of the culture, but I think part of it is that we are mission aligned, that everyone that comes to work with us believes in entrepreneurship is important and that Shopify is spreading entrepreneurship in a disproportionate way to pretty much anybody else. Not to say there's not other people doing it, but we are doing it this massive scale. And if you feel that's important, you'll probably do really well at Shopify. Ilana Golan: And that's incredible. And by the way, it's interesting because we feel your passion, right? Like, I mean, I think everybody listening and people saying on YouTube, like it's contagious. Yeah, it has to be. I don't think you can fake it. Harley Finklestein: Going back to the fake it till you make it. You can fake it till you make it for a period of time. I did that with t shirts. The mentor of mine in 2005 who said, Your t shirt business is nice, but this is not going to be your life's work. That concept. He was right. I think where you find your life's work is [00:33:00] where your personal mission and your professional mission overlap. They don't have to overlap entirely, but where they begin to overlap, you begin to see glimmers of what people often refer to as life's work. And this idea of life's work is not something that my grandfather, my grandmother could have ever even, the term was not something they ever thought about because. That almost seems like a luxury. Well, it is a luxury to be able to do something that you feel deeply passionate about. They were doing something that they felt they had no choice but to do. But if you can find something like that, one, I think it makes you a lot happier, a lot more satisfied, a lot more optimistic. There's a lot more meaning in your life. But two, I think that's how you build the most successful businesses, is where you actually really care about it. We are not selling widgets anymore. Go back 50 years ago, and you look at the person running Coca Cola, or the person running Chrysler, or the person [00:34:00] running Goodyear tires. Unless it was a direct descendant of the family, I suspect that to them, it was just another widget. And whether they're selling soda, or selling tires, didn't matter to them. It was just, their job was to sell the thing, the widget. That's not the case anymore. We're actually a lot closer to the olden days where the baker sold bread, the cobbler sold shoes, and man, that cobbler really cared about their shoes. Ilana Golan: but what you said, I think is really, really important here in terms of when you talk about that zone of genius and that luxury. I remember one of my hardest moments was as you climb up the ladder, VP, whatever you get the salary, it's very comfortable. And even though it's killing you from the inside, you are feeling ungrateful, right? I have a roof over my head. I'm paying my kids. Why am I ungrateful? Why am I not happy? And so first of all, it comes with a little bit of shame around [00:35:00] how can I not be satisfied and grateful. And on the other hand, it's that nudge that actually made me leap and start Leap Academy, entrepreneurship, et cetera. And that created, I've never been this happy in my life. So how do you balance between that, you know, I would love to eventually also talk about that COO role, because I think that's also part of the story. Harley Finklestein: I was going to mention that particular example. So one is, I don't think you can trick your subconscious. You can tell yourself, you can, positive visualization and mindfulness practices. You can trick yourself for a period of time that what you're doing is the right thing. And actually, in some cases, You don't really have a choice. If things are going a particular way for you personally, or the company's in a state of change, you kind of just need to get it done. One of the major expressions you hear around Shopify is, Get shit done. Just get it done. We just need to get to the next stage of this [00:36:00] thing. And there are times where you just have to get shit done. I mentioned my kids. I have a five year old Zoe and an eight year old Bailey. When they were newborns, as anyone who, you know, who's a parent knows, There's no way to be mindful and be thoughtful when you have a newborn crying at four o'clock in the morning, and you haven't slept in five weeks, and you kind of just need to get it done. There's a time and a place just to get it done. Once the fog leaves and you have some clarity, that's where I think There is no trickier subconscious. And for me, in 2016, I was asked to be the Chief Operating Officer, COO of the company. And I wanted to be a really great COO. How you do anything is how you do everything. I wanted to be really great. And so I had mentors who were some of the best COOs of the largest companies talking to me, giving me advice. I was reading all these books, like writing Shotgun, which is the famous COO book. I was constantly trying to get better at this stuff that was required of me as a CEO of the company.[00:37:00] Something was missing. And so I did it. I made sure I gave it everything I could. But eventually, as I began to kind of think about, is this the best way for me to be increasing the value, increasing the velocity, making Shopify better? There was this thing that was nudging me, which is, I really am a storyteller. That's my craft. I'm not the best in the world at it, but I'd like to be one day. And, I think, I have a chance to be the best in the world one day at being a storyteller thing. I'm not sure I'm ever going to be the world's best COO. My mind is not in the weeds, in spreadsheets, constantly thinking about operational excellence. I can do it, but am I the best at it? And so eventually I had some really good discussions with Toby and with her board and just with the people around me and it became clear that this other thing, that is where I think I can add more value, I can learn more, I can create more [00:38:00] impact, and I'm just really going to enjoy it. Like that is my craft. I'm the president of the shop line. Our COO Kaz is exceptional COO. He's amazing what he does. He loves operational efficiency. He loves tweaking all those dials, getting a little bit more here and monitoring. He's just, he's so good at it. And it reminds you that the thing that you may not enjoy in your life, in your job, in your career, that is someone else's dream job. And the job I have right now is my dream job. It's the reason why I can spend my life doing it. Because it's high impact for the company. I feel like I'm learning a ton every single day. I get a lot of satisfaction from the work. I work 70 or 80 hours a week every week. I'm okay with that. In fact, I love it. I really enjoy it. So I think some of it, when you sort of think about the role that you're in right now, you have to ask yourself, Are you doing this because? You feel like you're going to let somebody else down if you didn't do [00:39:00] it? Is it ego? Is it that you just don't want to admit that this is not right for you? This idea of doing more of what you love, I think is an amazing thing. And we have this concept at Shopify which is really cool. It's called Tours of Duty. And a Tour of Duty is three years. It's really wonderful because it means that every three years you get an opportunity to reassess And address, how is it going? How's it going? And you can have these conversations for everyone that I work with. I know what their tours of duty and dates are, and we can have a conversation leading up to it as saying, how was that tour? Does it make sense to another tour like this? Or does it actually make more sense for you to do a different tour? How can you be most valuable to Shopify? How can Shopify be most valuable to what you want? And sometimes, not all the time, but sometimes those things really line up. And rather than being a jack of all trades, being very good at a lot of things, what if you went deep? So rather than being horizontal shaped, what if you actually are vertical and you go really deep into one thing? Is [00:40:00] that going to be better for your employer, your company? Is it better for your life? And every now and then, my feeling is, it often is, but it's very difficult to have those conversations. Now, let me preface all this by saying, it has to be at the right time. In the middle of the global pandemic, when things were going crazy, and all these offline businesses were moving online, and the market was in turmoil, and people were losing their jobs. That is the wrong time to be talking about, do I have the right rules? That is wartime, that is all about focusing on getting shit done. There are moments, because every company has ebbs and flows, there are moments where you're in a particular period, you're like, alright, I'm getting the hang of this, maybe it's the right time for me to figure out whether or not, for the next tour of duty, I should try something different. Ilana Golan: That's brilliant, the tour of duty. And I think a lot of it is hardly experimentation anyway, right? Because whatever you studied at age 20 is [00:41:00] irrelevant to what you're doing usually anyway. So if you don't experiment, how can you tell? But talk to us a little bit about COVID because there was definitely some changes that needed to happen. It was a stressful time for everybody. Retailers were closing doors in many cases. Can you talk a little bit about it? Harley Finklestein: I mean, COVID was, was wild for, I think, anyone, certainly for us. If you think about e commerce as a percentage of retail, we basically had. three to five years worth of acceleration in that growth rate of e commerce in eight weeks. So all of a sudden, all these physical retailers had never sold online were coming to Shopify to sell online and we had to be ready for them. And so I'm actually really, really proud of how Shopify showed up during COVID. There's this great metaphor that a friend of mine uses, which is the tidal wave that when a tidal wave is coming, there are two types of people. There are the towel people and the surfboard people. The towel people grab their towel and run for the shore. And [00:42:00] the surfboard people grab their surfer and run for the tidal wave and surf it. Shopify is a surfboard company. We see these tidal waves coming and we don't retreat. We jump in and figure out how do we surf these new waves? What do we need to know that we don't already know? And so we throw out our roadmaps in 2020 and we said, what are the things we have to do right now? We have to extend, we have a capital product for cash advances, whereby we were in one country, I think we're in the U. S. We're like, we need cash advances for Canada and the U. K. as fast as possible, where a large chunk of our merchants are as well, in addition to the U. S. We needed to have curbside pickup. We needed touchless pins for point of sale so you can avoid contamination with COVID. We focused on the things that were most important, and I don't think companies should be gauged, or I don't think you should look at companies, you know, In terms of how they do in times of when everything is fine, I think the true gauge of a company's culture, a company's [00:43:00] strength or performance is in times of great change, call it wartime or peacetime, whatever term you want to use. But that's when you see the very nature, the actual true character of a company. Of a company and it was one of my proudest moments is watching how Shopify and our team operated in those years because it wasn't about us. It was about how do we help small businesses and mediums of businesses, not just survive this thing, but thrive and companies like Mattel, which is, you know, it's been around for 80 years. They created Mattel creations at that time, companies like figs started handing out nurses uniforms, doctor uniforms to frontline workers. You saw it. All these incredible companies all over the world that were supported and powered by Shopify were doing their, creating their own impact in their own communities, in their own industries. It was an amazing thing, but I'm glad it's behind us. That was a very stressful time, but I'm very proud of how our company showed up for certainly the [00:44:00] first global pandemic of my lifetime. Ilana Golan: And to me, I think that's a lot about that adaptability. But speaking of incredible times. Black Friday and Cyber Monday are historically massive for Shopify and for everybody on the platform. Why is it such a great opportunity? And talk a little bit about the numbers because you, Harley Finklestein: Oh, yeah, the numbers are crazy. So, uh, so it used to just be Black Friday, and then it became Black Friday and then Saturday, Sunday, and then Cyber Monday was added. And then it was Black Friday, Cyber Monday weekend, four days. Then it became a week. And then it became a month. And now it's almost like a season. Like, once back to school is over, you begin to sort of think about the holiday shopping season, which is epitomized by BFCM, or Black Friday, Cyber Monday. The reason it's so meaningful to us is because We have millions of stores on our platform for a lot of them, that is their Superbowl that they make not just in terms of the money they make, but that's when they engage with the [00:45:00] most amount of customers, they have the most amount of shipments, they have the most amount of attention on them. And so our feeling is being the guardians and the support system for these millions of businesses and stores. Is that we need to make sure they show up in the best way possible. And so if they're Super Bowl, but we're there making sure that they have all the stability they need, whether it's a company like Supreme who does these massive flash sales every Thursday, they have a flash sale. It's always the largest flash sale that they've ever had. So, the amount of throughput, the amount of infrastructure that's required, is an engineering marvel. And we have to make sure that they can do anything they want without ever slowing down. And, you know, whether it's Taylor Swift who sells on Shopify, or it's Kith who's launching a new, you know, collaboration with Giorgio Armani. These are iconic retail brands and they rely on us. And so it's their time to shine, but it's our [00:46:00] time to show up behind the scenes and make sure they have everything they need. And in 2023 from Black Friday to Cyber Monday, we saw about 9. 3 billion with a B sold on Shopify this year. Hopefully it will be even larger than that, but it's. If you love entrepreneurship the way we do, the way I do, I think you do too, Alana, like, this is where the spotlight of the world is on entrepreneurs. And we as consumers, we support them. We vote with our wallets to buy from small businesses, from local businesses, from brands. Every time we buy something from a brand, Whatever the brand may be, including, you know, big brand like Apple, we are voting with our wallets for more Apple to exist in the world. Every time we buy something from a small business, it's a local seltzer company, uh, Bicco from Montreal. Every time we buy, you know, soda water from Bicco, I am voting with my wallet to say, I like what your product is. is I like drinking it's delicious, you know, delicious water, but I want to see [00:47:00] more companies like this exist in the world and commercial retail. It's not just transactional. There is deeper meaning in it. And that's what I think. BFCM, those four days epitomize. Ilana Golan: Amazing. This is so, so strong and the numbers are insane. I have to say, like, I need to wrap my head around it. Harley, what would you say is maybe something that maybe sometimes people don't necessarily know about you, but that builds you to who you are today? Harley Finklestein: I mean, I mentioned mentorship a little bit. Mentorship is very important to me. I sort of built myself a bit of a personal board of directors. And it's not permanent. Every couple of years I swap one out for another one. Someone who I feel like is not necessarily, maybe I've learned everything I can from that person. Or maybe that person is, has taken a different track. But I have this sort of personal board of directors in my life. And as I grow and as I need new things, you know, I'm a new dad now. So I didn't really have anyone in my life who I thought was a really great father. And so I've added more people to the board of [00:48:00] directors now, of my own board of directors, who are great fathers because I want to learn from them. So. That's sort of one thing, I think. I want it to be very well rounded. At some point, someone must have told me, if you're going to be a leader of a company like Shopify, you have to be very well rounded. I'm not well rounded. I don't really want to be well rounded. I want to be really spiky. I want to be really spiky and really sharp on the thing that, that I care most about. Storytelling, being Shopify's president, telling our, our narrative to the world, to investors, to the public, to the media, to merchants, to partners, to everybody. And I'm want to be self aware enough to know all the other stuff that I'm not good at and then invite people in to help me with the things that I'm not good at. So maybe that's the second one. Maybe the third one is, I mentioned my kids a few times. I recently wrote a kid's book. It's called We Can Be Entrepreneurs. I want more people to have the business card experience when they're kids. I want more parents to be talking to their children about, hey, The famous question, what do you want to be when you grow [00:49:00] up, is the question I hate the most. My kids were asked it, it led me to write a kid's book about that very question, because I never asked that question. When I said, my parents said, what if you did this right now? And what if we made you feel like you can do it right now? And that ultimately has led to my entire life, my entire career, my, me being at Shopify, is that no one ever asked me what I want to be when I grow up. Instead, I was told you can do whatever you want right now. And this is not my childhood. I didn't grow up wealthy. I didn't grow up with a lot of money around. I went to public school in South Florida. Big public school at 5, 000 kids, not a rough environment per se, but this wasn't like some sort of pampered existence. And those are the things right now that I think a lot about that have led me here. And this idea of how you do anything is how you do everything as a personal motto, as a family motto means the things that Lindsay and I, my wife and I work on together are always deeply intentional. Ilana Golan: So maybe last question for you, Harley, because [00:50:00] these are such important points. Our listeners, many of them, are either want to go to entrepreneurship, but are afraid. Some of them are starting, but it's really hard to find the first client. What would you say to people who are debating, they're afraid of the financial element, they're afraid of what will people say, what if I fail, like there's a lot of fear around it, Harley. What would you say to them? Harley Finklestein: I would say to remember that the cost of failure in 2024 and beyond. is the lowest it's ever been when it comes to entrepreneurship. The lowest. What I mean by that is if you try something and it works. You can build a multi billion dollar company. And if it doesn't work, it's not as if it's going to change your life dramatically. Because what now costs 39 a month on Shopify. This isn't a pitch for Shopify, but just to quantify it. Which a lot of people spend on [00:51:00] coffee. On a monthly basis, right? Like Starbucks coffee or a lunch or something like that for the cost of a couple Starbucks coffees, you can start a business today and because the Internet has democratized distribution because the tools like Shopify and and some things you're doing a leap Academy have made it easier to learn these things you can build something faster, more effectively. But again, if it doesn't work, okay. The cost of failure is as low as it's ever been. Whereas for my grandfather, the cost of failure would have been losing his home, not a nice home, but whatever home he had, or not putting food on the table. That's not the case anymore. So if you think it's hard, it is. If you think it's complicated, it is. But also, you can do it. And you don't have to have experience in it. Some of the largest stores on Shopify that sell billions of dollars, this is their first business. They've never done it before. It's not expensive anymore. It used to be hundreds of [00:52:00] thousands or millions of dollars, set up a beautiful online business. Now you can do it for 39. And if it doesn't work, you can just pivot and try something else and pivot and try something and you can start small. Let's say you're selling. bubbly water, you can go to Reddit, or go to Facebook, or go to, you know, X or Instagram, and you can find the other people who also love soda water, and you can just start a conversation. You can say, what are the three things you love about your favorite soda water, and what are the three things you hate? And you take those three things that they hate, and you actually make something that doesn't have, that has a list of those things. And you go back to those people and say, remember we had that conversation with soda water? I made a new soda water. It's an incredible time to be an entrepreneur right now, and it could potentially change your entire life. It could change the lives of your children and grandchildren. So, I don't know, it feels like there's a lot of talk about the doom and gloom around entrepreneurship, that there's been less entrepreneurs created in the last five years versus the previous 20 years. I don't know, it feels like we are entering into the golden age of entrepreneurship right now. [00:53:00] Ilana Golan: I agree a thousand percent, Harley. We call it in Leap Academy, the new possible. I think the plateau of possibilities is endless and I love that Shopify makes it so much easier for people to just try it out, you know, go for it. I love this. Harley, thank you so much for coming in the show. Crush it. Continue changing people's lives because it's just incredible and it's in the masses. Harley Finklestein: And you, you too, what you're doing with Leap is amazing. You're bringing more people into this arena, which I think is incredible. Thank you for having me on your amazing show. It's a real honor for me to be here.