Leap Academy with Ilana Golan
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
Thu, 14 Nov 2024
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: - His early roots in entrepreneurship - The t-shirt business that changed his life - How he set himself apart by overdelivering - Entrepreneurship as a tool for problem-solving - Why you must thrive in rapid change to stay relevant - Embracing ‘founder mode’ by focusing on the details - Why the future of entrepreneurship is limitless - How he became one of the first Shopify users - How Shopify built a mission-aligned culture - Finding your life’s work - And other topics… 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. As one of the "Dragons" on CBC's Next Gen Den, Harley brings his wealth of knowledge and experience to the forefront. His leadership extends beyond Shopify, having been on the Board of Directors for the C100 and the CBC. He’s also a proud member of the Order of Ottawa and currently serves on the board of Operation Hope, focusing on financial literacy empowerment. Connect with Harley: Harley’s Website: http://harleyf.com/about/ Harley’s LinkedIn: https://www.linkedin.com/in/harleyf/?originalSubdomain=ca Harley’s Twitter: https://twitter.com/harleyF Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training
Chapter 1: What inspired Harley Finkelstein to become an entrepreneur?
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, something with great meaning. He was passionate about surviving.
not passionate about the entrepreneurial venture themselves. And so I think the fortunate opportunity that I had was my parents didn't look at entrepreneurship as a luxury, as this creative outlet. They viewed it as a way to solve problems because that's what they saw their parents using it for as well.
And like you said, when you're an entrepreneur, you wear trizillion 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 know, call it a superpower that I really want to copy or really want to emulate. What I realized was there is no one person that exists on the planet who I want to copy the entirety of them.
But I like one aspect of what they do. I like the way they parent. 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
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.
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Chapter 2: How did Harley's early experiences shape his entrepreneurial journey?
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.
But eventually, as I began to kind of think about, is this the best way for me to be increasing the value, increasing the velocity, making Shopify better? There was this thing that was nudging me, which is, I really am a storyteller. That's my craft. I'm not the best in the world at it, but I'd like to be one day.
And I think I have a chance to be the best in the world one day at being 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 going to enjoy it. Like that is my craft. And today, I'm the president of Shopify. Our COO, Kaz, is an exceptional COO.
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.
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.
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.
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.
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.
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