Harley Finkelstein
Appearances
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 can join him and a small group of engineers, mostly engineers, and help them build the business.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And that was 15 years ago.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
More than a third of my life. Yeah.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
I think companies are like that also. I think when you were 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And I think to be successful in any organization, again, early or even later stage, you have to figure out what the cadence of change is 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,
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 the early days of Shopify, we didn't have a CFO.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
At that point, you have no choice but to learn an incredible clip because 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 re-qualify for the next phase. And if you don't, you don't deserve to be the next phase.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
So as you said, as a kid, I was always entrepreneurial. I always had, 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 $100 billion global 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And what the famous, what got you here won't 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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. 10 years after he started in 2022, Gymshark was a billion dollar company competing with Nike. In the history of the world,
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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,
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 is as much of a meritocracy. It's not a perfect meritocracy.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
You asked specifically some of the things 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, 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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,
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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. 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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. 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
James Purse thinks as much about black t-shirts as Elon Musk thinks about rockets and thinks about lithium ion batteries. There are these people that get so interested in these challenging things. I love that. That inspires me.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
You'll never really know exactly what number you're at. You're never going to say I'm at 87% 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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'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
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 of inviting more people into entrepreneurship means that the people that use Shopify, they can find their own versions of success.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 is the founder of Figs, they completely disrupted the modern-day fashion hospital scrub industry.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And so what we try to do at Shopify is, because we're a company focused on entrepreneurs, we try to hire entrepreneurs. 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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. We're about 8,000 people at the company today.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 that entrepreneurship is important and that Shopify is 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And if you feel that's important, you'll probably do really well at Shopify.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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. 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 your personal mission and your professional mission overlap.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
Well, it is a luxury to be able to do something that you feel deeply passionate about. They were doing something that they felt that 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 thing. And there are times where you just have to get shit done. I mentioned my kids.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
I have a five-year-old Zoe and an eight-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 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
But 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 this chief operating officer, COO 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 COO of the company. But something was missing. And so I did it. I made sure I gave it everything I could.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And I think I have a chance to be the best in 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 going to enjoy it. Like that is my craft. And today, I'm the president of Shopify. Our COO, Kaz, is an exceptional COO.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
He's amazing at 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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'm really enjoying it.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 gonna let somebody else down if you didn't do it? Is it ego? Is it that you just don't wanna admit that this is not right for you? But this idea of doing more of what you love I think is an amazing thing.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 is it going? And you can have these conversations. For everyone that I work with, I know what their Tours of Duty end dates are.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And we can have a conversation leading up to it as saying, how was that tour? Does it make sense to do 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 that going to be better for your employer, your company? Is it better for your life?
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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,
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
when things were going crazy and all these offline businesses 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
But there are moments, because every company has ebbs and flows, there are moments where you're in a particular period, 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And the surfboard people grab their surfboard 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 things we have to do right now? We have to extend.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
We have a capital product for cash advances whereby we were in one country, I think we were 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 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, call it wartime or peacetime, whatever term you want to use.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
Actually, I'm going to show you something I've never showed anyone.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 medium-sized businesses not just survive this thing, but thrive. And companies like Mattel, which has been around for 80 years,
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
They created Mattel Creations at that time. Companies like FIGS started handing out nurses' uniforms, doctors' uniforms to frontline workers. You saw all these incredible companies all over the world that were supported and powered by Shopify were 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
This was actually my very first business card. And if you can see it, it says Fresh Vibe Entertainments. The reason I have this 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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...
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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,
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
Or it's Kith who's launching a new 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 time to show up behind the scenes and make sure they're 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
But it's... If you love entrepreneurship the way we do, the way I do, I think you do too, Alana. 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 might be, including a big brand like Apple.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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, Bitco from Montreal. Every time we buy soda water from Bitco, I'm voting with my wallet to say, I like what your product is. I like drinking it. It's delicious, you know, delicious water. But I want to see more companies like this exist in the world.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 has taken a different track.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 directors now, 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 up? is the question I hate the most.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 grow up.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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,
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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, 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 to 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 else.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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, 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?
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 business.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
We all have dark places we go to, and the question is, how do you get out of those dark places? So things were things were about as dark as they could have gotten. It was desperation. I didn't really know what to do.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 card's not very fancy and it just says Fresh Vibe Entertainment.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
It 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And so a friend of mine was on student council at McGill University and told me that McGill Thank you. I knew that Montreal historically had a very prominent schmata business, clothing industry. You have companies like American Apparel and Buffalo Jeans and Parasuco and Aldo and Brown. A lot of big companies that are now global companies were built.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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. It wasn't about t-shirts at all. It was...
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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. They were all kind of boxy. The logos didn't look very nice.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 teacher business. I didn't. Fake it till you make it. But I told them I had a teacher business.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 believed this idea of just always over-deliver. Everything you do, over-deliver.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And so I think their test order was for like 100 t-shirts, and I brought in 120 t-shirts. And I gave them 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 everything.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
So I gave them my cell phone number and said, if there's any problems at all, give me a shout. That first t-shirt went off without a hitch. It was fantastic. Then I began to realize that I can use the same model at other universities. where I would go in, I mostly focused on Canada, but I had friends at every university across Canada at that point, or at least I knew someone at each university.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
I used this tool called entrepreneurship when I was 17 to solve this problem. It changed my life. You can start a business today. It's an incredible time to be an entrepreneur right now 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 effective.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 working samples, physically printed samples.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
But I like one aspect of what they do. I like the way they parent. They're great mom or dads. Or they're 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
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
Well, 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
So I had a mentor of mine who convinced me that... How did you even start? Actually, I'm going to show you something I've never shown anyone.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
And he happened to be teaching 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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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. The business model just broke if I had to go to class.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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. 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. I was an entrepreneur.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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.
Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
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. They still are to this day. And I asked where the entrepreneurs hung out in Ottawa. And I was directed to a coffee shop
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
So actually, I think this idea of the creator economy, it's just the economy, except that there's this really cool advantage, which is that you have a built-in audience for your products. And maybe third of all, just sort of on the larger companies, a lot of companies either never sold direct to consumer. If you think about the CPGs, for example, Heinz Ketchup has a store on Shopify.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
Heinz Ketchup never sold direct to consumer. Heinz would sell through a grocery store. But there's some people that really care about, like, they're obsessed with ketchup. They love ketchup. And they want to buy direct from Heinz called Heinz at Home. And for the first time ever, those big brands are actually having direct relationship, whether it's through social media.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
I remember years ago, the Wendy's account was like, had a real personality. And a lot of these social media accounts of big brands actually have personalities to the extent that their fans, their consumers want to interact with them. And so you have a couple of things happening with the big companies. One is the big companies are beginning to act a lot more entrepreneurial.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
They want to have a direct relationship with the consumer. But also, they're experimenting. They're trying new things. A couple years ago, one of the cool things I thought that Oreo did, which is owned by Mondelez, is you can put, as a Christmas gift or holiday gift, you can put, you can personalize Oreos. So there's someone in your life that loves Oreos.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
You can make a, you know, Harley's, Harley's, you know, um, Harley's Oreos, happy holiday, something like that. That is really interesting. So when you come, so each of those things on their own are kind of interesting. When you combine those things, you see big companies acting very entrepreneurial.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
You think you see creators, uh, just, just on the creator side, think about these artists, like these musicians, people like, um, you know, drew house with, with Justin Bieber's brand that he built, or OVO, what Drake has built. You see these traditional, you know, what would be a traditional musician completely expand their scope of what they're actually building and selling and creating.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
When I used to go to a concert when I was a kid, I would go to the merch table. It was usually some sort of like shitty screen print on some basic t-shirts, like Fruit of the Loom t-shirt. And it said like, I don't know, the Rolling Stones on the back was a bunch of tour dates.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
Well, now you go to these concerts and you go to like a Drake concert and they're selling like Canada Goose OVO collab jackets. Or you go to, you know, a Pharrell concert and you see some of the crazy stuff he's selling that like, you know, he's selling like cosmetics at the concert that he's created himself. So big companies are actually entrepreneurial.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
Artists are now actually expanding from just being, artistic creators around music and art and film to actually creating product. And you can even look at the actors and actresses that have done. And then of course you have just more people generally becoming entrepreneurs and more people saying, I make amazing chicken soup and now I'm going to sell that chicken soup to the world.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
And I think when you combine all those things, you see people that traditionally had not entered entrepreneurship doing so. And they're scaling at a pace that just has never been seen before. And that's why that's a long answer to a very short question. But that's why I think there's an entrepreneurial renaissance happening.
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
So actually, I think this idea of the creator economy, it's just the economy, except that there's this really cool advantage, which is that you have a built-in audience for your products. And maybe third of all, just sort of on the larger companies, a lot of companies either never sold direct to consumer. If you think about the CPGs, for example, Heinz Ketchup has a store on Shopify.
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
Heinz Ketchup never sold direct to consumer. Heinz would sell through a grocery store. But there's some people that really care about, like, they're obsessed with ketchup. They love ketchup. And they want to buy direct from Heinz called Heinz at Home. And for the first time ever, those big brands are actually having direct relationship, whether it's through social media.
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
I remember years ago, the Wendy's account had a real personality. And a lot of these social media accounts of big brands actually have personalities to the extent that their fans, their consumers want to interact with them. And so you have a couple of things happening with the big companies. One is the big companies are beginning to act a lot more entrepreneurial.
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
They want to have a direct relationship with the consumer, but also they're experimenting. They're trying new things. A couple of years ago, one of the cool things I thought that Oreo did, which is owned by Mondelez, is you can put as a Christmas gift or holiday gift, You can put, you can personalize Oreos. So there's someone in your life that loves Oreos.
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
You can make a, you know, Harley's, Harley's, you know, Harley's Oreos, Happy Holiday, something like that. That is really interesting. So when you come, so each of those things on their own are kind of interesting. When you combine those things, you see big companies acting very entrepreneurial. You think, you see creators, just on the creator side. Think about these artists, like these musicians.
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
People like, you know, Drew House with Justin Bieber's brand that he built. or OVO what Drake has built. You see these traditional, you know, what would be a traditional musician completely expand their scope of what they're actually building and selling and creating. When I used to go to a concert when I was a kid, I would go to the merch table.
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
It was usually some sort of like shitty screen print on some basic t-shirts, like Fruit of the Loom t-shirt. And it said like, I don't know, the Rolling Stones on the back was a bunch of tour dates. Well, now you go to these concerts and you go to like a Drake concert and they're selling like Canada Goose OVO collab jackets.
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
Or you go to, you know, a Pharrell concert and you see some of the crazy stuff he's selling that like, you know, he's selling like cosmetics at the concert that he's created himself. So big companies are actually entrepreneurial. Artists are now actually expanding from just being, artistic creators around music and art and film to actually creating product.
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
And you can even look at the actors and actresses that have done. And then of course you have just more people generally becoming entrepreneurs and more people saying, I make amazing chicken soup and now I'm gonna sell that chicken soup to the world. And I think when you combine all those things, you see people that traditionally had not entered entrepreneurship doing so.
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
And they're scaling at a pace that just has never been seen before. And that's why that's a long answer to a very short question. But that's why I think there's an entrepreneurial renaissance happening.