Leap Academy with Ilana Golan - Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53

Episode Date: September 29, 2026

We’re bringing back one of our favorite conversations from the Leap Academy podcast with Shopify President Harley Finkelstein. Harley Finkelstein didn’t set out to be an entrepreneur. He had no choice. With his father out of the picture, he had to pay for university and support his mother and sisters. So, he turned to his go-to problem-solving tool: entrepreneurship. Starting a t-shirt business changed his life, eventually leading him to Shopify, where he became one of their first merchants and later, its president. In this episode, Harley shares his incredible journey, highlighting key lessons on how entrepreneurship can solve real-life problems and the power of adapting quickly in a fast-changing world.Harley Finkelstein is the President of Shopify. He is also an entrepreneur, lawyer, and investor. He is one of the “Dragons” on CBC’s Next Gen Den and has been recognized among Canada’s Top 40 Under 40 and Fortune’s 40 Under 40. In this episode, Ilana and Harley will discuss: 00:00 Introduction 01:11 Early Entrepreneurial Ventures 07:44 College Years and T-Shirt Business 14:14 Transition to Shopify 19:39 Challenges and Growth at Shopify 45:56 COVID-19 Impact and Adaptation 49:31 Black Friday and Cyber Monday Insights 53:27 Mentorship and Personal Growth 56:31 Encouragement for Aspiring Entrepreneurs 59:57 Conclusion and Final Thoughts Harley Finkelstein is an entrepreneur, lawyer, and President of Shopify. He is an advisor to Felicis Ventures and a notable investor. He has been recognized as Canadian Angel Investor of the Year and among Canada's Top 40 Under 40. Connect with Harley: Harley’s Website: harleyf.com Harley’s LinkedIn: Harley Finkelstein on LinkedIn Harley’s Twitter: @harleyf 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/

We all have dark places we go to, and the question is how to get out of those dark places. So things were about as dark as they could have gotten. It was desperation. I didn't really know what to do. I had a dream, ma'am. I am going to make it. Harley Fickoste, president of Shopify, valued at $100 billion. They're helping millions of businesses and entrepreneurs across the globe, start, sell, and grow their businesses.

I used this tool called entrepreneurship when I was 17 to solve this problem. change my life. You can start a business today. It's an incredible time to be entrepreneur right now. Because the tools like Shopify and some things are doing at Leap Academy have made it easier to learn these things. You can build something faster, more effective. How did you join Shopify and how did that all happen? So I had a mentor of mine who convinced me that... How did you even start? Actually, I'm going to show you some that I've never showed anyone. This. You started entrepreneurship when you started entrepreneurship when you, you started entrepreneurship when You literally had no choice.

You did a bit as a kid. We'll talk about that too. But you leaped entrepreneurship in a very, very dark place personally and for the family. Can you share what happened, Arlie? 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 in some 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 too much younger sisters that were living down back in Florida with my mom. And things were about as dark as they could have gotten.

And I decided that point that in a similar vein to when I was younger and I want 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-shirt 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 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 see 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. Wow. I never thought of entrepreneurship as

a problem solving, which I guess it is. But I want you to just take me back in time then to this 14-year-old that decides to be a DJ, how did you even start? Actually, I'm going to show you some ahead. I've never showed anyone. I like that. This was actually my very first business card. And as you can see it, it says fresh vibe entertainments.

The reason I have is because my mother recently found it 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 bat 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 quiet, eating their dinner. 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 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 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 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 love 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 $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 into a small 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. 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, all the typical car creators, right? 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. It's 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 car 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 the beginnings of this. It made it real. 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. So take us a little bit towards college, because you're also learning something that is completely not what you do today. but take us a little bit there. 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 and is 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 Miguel spends $25,000 a year on t-shirts, promotional t-shirts. So faculty of science or faculty

of arts or 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 schmanta business, clothing industry. You have companies like American Apparel and Buffalo jeans and Parasucco and Aldo and Brownsh. A lot of big companies that are now global companies were built. Gilden, 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 where I can buy blank t-shirts from.

And it wasn't this big, passionate, I need to be in the T-shirt. I loved, it wasn't about T-shirts at all. It was, I thought it in an opportunity that McGill buys T-shirts. I was a McGill student. Most of the T-shirts that I had worn that Miguel 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.

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 at McGill and telling them I'm a student here. I told them I have a t-shirt business. I didn't.

They could tell you make it. But I told them I had a teacher 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 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 any problems at all, give me a shout. And that first t-shirter 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 it introduced 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, I would go in with actual 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 samples. And by the end of university, 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. 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. 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 paternal grandfather was able to have in Canada,

in the new world in his nomenclature was he was able to start a little business. 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, and somebody 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 outlets. They viewed it as a way to solve problems

because that's what they saw their parents using it for as well. And like you said, when you're an entrepreneur, you wear Brazilian 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 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?

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. usually the group of mentors each has one, I don't 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 in 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 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, while the T-Shure Business was a good business, that that wasn't ever going to lead to having a large enough impact. And the T-Shure 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 learned 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. I 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 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 $10,000 or $15,000 worth of value. And so I didn't get caught up in grades and exams because I wasn't why I was there. I was there to extract value, to gain new skills. But as we 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, quote, 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, 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 then 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, 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 can join him and a small group of engineers, mostly engineers, and helped them build the business. And that was 15 years ago. Incredible. So it's almost a third of your life, but who's counting? More than a third of my life. Yeah.

Crazy. Okay. But early stage, when you start something, there's going to be trisillion challenges, especially because how fast Shopify grew. Can you share a little bit of the beginning? some hard moments that you all needed to confront. 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. Darwin in the making, exactly. That's exactly right. 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 out what the cadence of changes and make sure you are adapting 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 to solve? And I'll go focus on that. So they really is to 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 focused 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 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 some of them did not. At that point, you have no choice but to learn at an incredible clip because in those early days, back to the law of ecology, the rate of change of the business

of the company 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 re-qualify 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 one trillion with a T,

the one trillion dollar 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. 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 changed 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 $100 billion global commerce platform is that the people that work at Shopify, to be successful, we expect that they re-qualify every year for their job based on what the company requires of them. And what the famous, what got you here, we'll 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. 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 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. 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 Jim Shark. Jim Shark is a merchant on Shopify. Ben Francis started that company in 2012. Ten years after he started in 2022, Jim Shark 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 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 an easy, easier way to grow into scale. That is not the case. Today, entrepreneurship is as much of a meritocracy as it's not a perfect meritocracy. There are still people that don't have access to the internet around the world. So obviously there are some people that are starting from further back in the race. But 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. 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 other stop. You asked specifically some of the things that that helped me climb. Let me be very specific. A 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, set it on stage a few months ago, and there's been a bunch of blonde posts

and articles written about Founder Mode. Founder mode is very simple. 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 every word choice I use is specifically geared towards the message, the audience, the timing 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 my business. That works less well in my marriage. I mean that my wife and I have a great relationship. I've said this publicly before, but since getting married 11 years ago, we've been seeing a couple's 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. It 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 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 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% trust battery. and over time with consistency and them doing what they say they're going to do

and you doing what you say you're going to do, the trust battery goes up and eventually 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 do everything. And to me, that's just a proxy for intentionality. I think that I put as much effort into editing those quarterly earnings 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 the 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. I don't wear a suit every day.

I wear a black t-shirt, but the person who makes my black t-shirts, the name is James Purse. James Perce 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.

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. You'll never really know exactly what number. You're never going to say I'm at 87% or 50%, 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. 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 cultures to the mission. Can you talk a little bit about that, Harley? Yeah. 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 is 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 incredible results. Our mission is very simple. We want to create more entrepreneurship. Full stop. And this idea, inviting more people into entrepreneurship means that the people that use Shopify, they can find their own versions of success. For Ben Francis from Jim Sharick, like I mentioned earlier, his definition was to change the athletic apparel industry. And he did. Jim Shark is incredible. They can be with the biggest companies on the planet. In the case of Trina, who is the founder of Figgs,

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 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 of 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, that want to learn more about them. And I'm really proud of the culture we built the shop. We're about 8,000 people at the company today. I'm very proud of the culture. But I think part of it is that that we are mission aligned, that everyone that comes to work with us believes that 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 at this massive scale. And if you feel that's important, you'll probably do really well at Shopify. And that's incredible. And by the way, it's interesting because we feel your passion, right? I mean, I think everybody listening and people sing on YouTube, like, you see the passion. It's contagious. Yeah. Thank you.

It has to be. I don't think you can fake it. Going back to a little fake it until you make it. You can fake it until you make it for a period of time. I did that with T-shirts. But 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.

That I think where you find your life's work is where you're. 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 or 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 deep, but 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, but there's a lot more meaning of 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 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, it 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. But what you said, I think, is really, very 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 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 rule

because I think that's also part of the story. 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 companies in a state of change, you kind of just needs 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 thing. And there are times where you just have to get shit done. I mentioned my kids. I have a 5-year-old Zoe and an 8-year-old Bailey. When they were newborns, as anyone who is a parent knows, there's no way to be mindful and be thoughtful

when you have a newborn crying at 4 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. But once the fog leaves, 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 this chief operating officer, CEO of the company,

and I want to be a really great COO. How you do anything is how you do everything. I want to be really great. 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 Riding 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. But something was missing. And so I did it. I made sure

I gave 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 think, I'm a story tell you. And I think, I'm a I think I have a chance to be the best the world one day at being the 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?

I don't think so. 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 impact, and I'm just really good to enjoy it. Like, that is my craft. And today, I'm in the president's shop, our COO, Kazz's 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, and 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 to let somebody else down if you didn't do it? Is it ego? Is it that you just don't want to admit that this is not right for you? But this idea of doing more of what you love, I think is an amazing thing. And we have this concept of 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 every three years you get an opportunity to reassess and address how is it going. How does it go? 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 win deep? So rather than being horizontal shaped, what if you actually are vertical and you go really deep into one thing? Is 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 business were moving online. and the market was in turmoil and people 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. But there are moments,

because every company has ebbs and flows, there are moments where you're in a particular peer, you're like, all right, 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. 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 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? Yeah, I mean, COVID 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 shop they 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 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 do 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 we're most in place.

important. And I don't think companies should be engaged or I don't think you should look at companies 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 strength or performance is in times of great change, called 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. 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 has been around for 80 years, they created Mattel creations at that time. Companies like Figgs started handing out nurses uniforms, doctors uniforms to frontline workers. You saw all these incredible companies all over the world that were supported and powerful by Shopify, we're creating their own impact in their own communities and 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 first global pandemic of my lifetime. 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 guys are. Oh, yeah, the numbers are crazy. 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 Super Bowl, that they make, not just in terms of the money they make, but that's when they engage with the most amount of customers. They have the most amount of

shipments. They have the most amount of attention on them. And so our feeling as 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 it's their 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 whether it's Taylor Swift, who sells on Shopify,

or it's Kith who's launching a new collaboration with Georgia or Armani. These are iconic retail brands, and they rely on us. And so it's their time to shine, but it's our time to show up behind the scenes and make sure they're going to need. And in 2023, from Black Friday and 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, Atlanta. 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, a 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 is a local

seltzer company, Bickho 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. I like drinking. It's delicious, you know, delicious water. But I want to see more companies like this exist in the world. In commercial retail, it's not just transactional. There is deeper meaning in it. And that's what I think BFCM, those four days, epitomize. 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 built you to who you are today? 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 swapped 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 has taken a different track. But I have the 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 directors now, of my own board directors, who are great fathers because I want to learn from them.

So that's sort of one thing, I think. I wanted 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, if you've been 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 I care most about, storytelling, being Shopify's president, telling our narrative to the world, to investors, to the public, to the media, to merchants, to partners, to everybody. And I 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 their children about, hey, the famous question, what do you want to be when you grow 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, me being a Shopify, is that no one ever asked me what I want to be when I grew 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, 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. So maybe last question for you, Harley, because these are such important points. Our listeners, many of them are either. They wanted 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? 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 coffee on a monthly basis, like Starbucks coffee or a lunch or something like that. For the cost of a couple Star Wars coffees, you can start a business today. And because the internet has democratized distribution, because the tools like Shopify and some things you're doing at Leap Academy have made it easier to learn these things, you can build something faster, more effectively. But again, if it doesn't work, 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 through 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 thousands or millions of dollars set up a beautiful online business. Now you can do it for 30,000. 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 X or Instagram. 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 three things you hate? And you take those three things that they hate and you actually make something that doesn't have, that is 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. 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. And 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.