Harley Finkelstein on having an entrepreneurial mindset

Be less concerned with your title, be less concerned about your self-identity within the company, be more concerned about like be an archaeologist. Find something that you say, hey, no one's really focused on this, but I think I can make a really big impact. Welcome to The Path where I, Ryan Roslansky, sit down with the biggest changemakers, innovators, and thought leaders in the world. And at the end, we'll see what turning point shaped the journey of these incredible success stories. Today, I sit down with Harley Finkelstein. Harley is the president of Shopify, an e-commerce platform where businesses can easily set up an online store without writing a single line of code. You've probably used it a bunch of times without even realizing it. Shopify makes up 10% of all US e-commerce, but his journey to running a multinational company was a unique one. He was a DJ, a T-shirt salesman, and even a lawyer. Here's how Harley Finkelstein paved his path. I want to go way, way back in time. Maybe to the first time you ever remember even thinking about what you maybe wanted to be when you grew up. Let me kind of start before I was even born, because my family's story, I think, plays such a big role, not just in our trajectory or our interest, but even in terms of how we think about career in general. My grandparents were Holocaust survivors. They came to Canada in 1956 from Hungary during the Hungarian Revolution. And my grandfather, the only thing he could do when he got to Canada because he had no money, had no family, had no friends, had no, didn't speak the language, was to sell eggs at a farmer's market. It was a way for him to put food on the table using entrepreneurship as a tool for survival. Fast forward, till I guess mid '90s, I'm 13 years old. I went to a lot of bar mitzvahs and bat mitzvahs. I would see these DJs on stage and they were like magicians to me. And so I became fascinated with this idea that I really want to be a DJ. And so I called around a bunch of DJ companies at the time, which of course the answer was no. So my dad said, "You know, why don't you consider starting your own DJ company and hiring yourself?" And that's what I did. I ended up DJing like 500 bar, bar mitzvahs, weddings, sweet Sixteens. A couple years later, I ended up going to McGill University. This is 2001 and Mom and Dad lost everything in the markets. And so once again I took out this tool called entrepreneurship and ended up building a T-shirt business, selling T-shirts to a bunch of other colleges in Canada. What was important to give you that confidence to just go and do it like that? One thing my father did throughout my life, anytime I had a silly business idea, he couldn't give me any money. But he made me a business card for every single idea. And I'm pretty sure in hindsight he probably made that business card like on the family computer on some crappy printer. But it gave me this audacity and it gave me validation, it gave me this confidence that, okay, maybe I'm not so crazy, maybe I could do that. But there were a couple of things that really played a big role here. One was entrepreneurship. Although it's exciting and interesting and compelling, it is also very, very lonely. And I've been really lucky throughout my life that as I was starting businesses, I always had other people that were my peers that were also starting kind of these crazy businesses as well. And by cultivating a bit of a community, it made entrepreneurship and the journey of entrepreneurship a lot less lonely. The second one was this idea that failure is not failure per se, but it's more of the discovery of something that did not work. The DJ business and the T-shirt business, which kind of worked out, there's been like a dozen or two other businesses between those times that did not work out that I'm not even talking about. But this ability to be incredibly resilient, whereby if I tried something, it didn't work, it didn't really affect my inner core belief or my self-identity. I love that. So there's a learning in every failure. One of the things that I found interesting in your path is that you actually decided to go to college. A lot of people, entrepreneur, just forego that step. What were you kind of thinking at that time instead of just going and starting something new again? I viewed education as being very transactional. I viewed it as I was paying money in the form of tuition, and in return, I want to receive a certain set of skills I can take with me in my entrepreneurial journey. A mentor of mine convinced me to go to law school. He felt that law school was this perfect place for me to acquire a set of really important entrepreneurial skills. The truth is, he was right. But because I looked at it as more of a transaction than sort of an experience, I cared less about whether or not I was attaining a certain grade or certain grade point average. I cared far more about, selfishly, was I actually getting better? Was I actually building my book of skills through the program? And I think that's a different maybe more refreshing way to think about academia and education. I love the framing, you know, how do you continuously make yourself stronger and better. By the way, did you ever practice law or no? I practiced law for 10 months. I didn't make it longer than 10 months. I thought practicing may actually give me this sort of new skill set like school did. And by month 3, it was clear, I wasn't learning proportionally to what my opportunity cost was. And so I called Tobi. To introduce Tobi, we need to rewind a bit. While Harley was building what he called his personal board of directors, he met a fellow entrepreneur, Tobi Lutke. Tobi was a computer programmer who was selling snowboards online. But in order to sell those products, he created a software that would later turn into Shopify. And Harley was one of its first users. I ended up becoming a store number 136 on Shopify, and I sold T-shirts all throughout law school and business school. The key though, was this one moment, I can remember it so clearly, where I was sitting in tax law class and I remember opening my, I had my laptop up and taking notes and I remember seeing an order come in and I was like, "Oh my God, I just sold the T-shirt." It just, I was blown away, that this 21-year-old kid with very little money sitting in law school in Ottawa, and I sold something to someone in Vermont. And it felt to me that if you combine someone with ambition, like I had, with this incredible tool, this like superpower, that I now call Shopify, these amazing things can happen that we can actually give people an unfair advantage. We can level the playing field in a way that business has really never been leveled. And so I called Tobi and said, "Look, you guys are three brilliant engineers. Let me come in and be your Swiss Army knife. I don't know what I'm going to do for you. I don't know how I'm going to help. But I will ensure that I come in and add value." And that was about 13 or 14 years ago. Harley would eventually become Shopify's Chief Platform Officer and COO, building up programs that made Shopify user friendly, all while bringing on corporations like Procter & Gamble, Tesla, and Red Bull. Today, Shopify hosts millions of merchants in more than 175 countries. To all of the entrepreneurs out there that are just getting started or think about going, what's your advice to someone right now thinking about starting their own company? Entrepreneurship is about as old as currency, and currency is about as old as time. So for thousands and thousands of years, entrepreneurship has existed. And for the first time ever, right now, as we sit here, the cost of failure is as low as it's ever been in the history of entrepreneurship. We are all talking about our highlight reels, most entrepreneurs really don't talk too much about their blooper reel, but we all have massive, massive blooper reels. We all have this line behind us of failed companies and failed ideas. But if you believe you're entrepreneurial but you don't know where to start, the best thing you can do is to find something that you're already doing and think about the commercialization of that. Okay, last thing, not everyone is going to be an entrepreneur. So when an employee inside of Shopify today comes to you and says, "Harley, what's your best career advice for me in general?" What do you normally tell someone? One of the best pieces of career advice that I ever received was, be less concerned with your title, be less concerned about your self-identity within the company, be more concerned about, like be an archaeologist, go deep on a particular topic and understand the history there, you can add more value. Find something that you see, hey, no one's really focused on this, but I think I can make a really big impact. But by sort of forgetting about the title and forgetting about some of the leveling, but rather focusing on how do I add the most amount of value. And the second thing I would say is that this idea of, like there's sort of this meme of hustle culture on social media, I actually think everyone needs to have a really good understanding of what they need to be at their best. If that means Friday night you have to, you know, you want to have dinner with your family or that means Saturday morning you want to go play tennis or you want to go mountain biking or you want to go for a walk, whatever those things are, the sooner you're able to figure out a way to have that in your life, it means you can have more sustainable growth as opposed to more of that growth that sort of, where eventually you end up burning out. So here's my takeaway. Entrepreneurs like Harley have a mindset that sets them up for success and often leads them to unpredictable paths. They are audacious and unafraid to fail. Just think of when Harley was 13 years old and no DJ would hire him. He had the confidence to just go for it anyway. He built a network of like-minded people to help him navigate a sometimes challenging and lonely journey. To me, the entrepreneurial mindset can help anyone unlock their full potential, even if you're not a business owner. And in the end, these tools will give you the ability to seize any given opportunity.