Behind the Brand with Harley Finkelstein

Behind the Brand with Harley Finkelstein

I was lucky enough to chat recently with Harley Finkelstein. He is probably best known for being the President of Shopify, but what I came to learn during the course of our chat was that his real passion is helping entrepreneurs.

Finkelstein was born in Montreal and told me that he is always interested in creating opportunities to solve problems. Finkelstein, who is Jewish, says that he began attending numerous bar and bat mitzvahs in his youth. He marveled at how the DJ, with just a few key phrases and inflection in their voice, could change the entire energy and vibe of the party. Finkelstein says he wanted to be a DJ, but couldn’t get hired, so he started his own company.

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Later, he started a T-Shirt company while attending McGill University, but it wasn’t until he was in Law School that he realized he needed a business that could run while he was in class. He met Shopify founder, Toby Lütke, became friends with him, and then became one of the first merchants on Shopify. Now, about a decade later, Finkelstein is running the show. He’s a brilliant mind, a fascinating teacher, and a self-proclaimed power extrovert. I was impressed by how many brilliant tips for entrepreneurs he could pack into our short interview. So here are some of my favorites. I’m calling it Harley Finkelstein’s Lessons in Entrepreneurship.

Ask yourself, was it a good day? 

Finkelstein mentions to me his admiration for the renowned author and speaker Jim Collins, who for a long time would rank himself on a scale of -2, -1, 0, +1, +2 to see how his day was. Finkelstein notes that after tracking his days for a long period of time, Collins would reverse-engineer how he had the days where he ranked the highest. Finkelstein says he does something similar.

“I did sort of make mental notes of the days that I thought I was feeling at my best. I was feeling most engaged, most excited, most productive; I was having the biggest impact and I just sort of noted, hey, like that was a good day, what did I do again? Oh, right I helped a bunch of entrepreneurs, oh, I spoke to this small business and helped them digitalize, or whatever it was…”


The second lesson that Finkelstein brings up is the Japanese concept of Ikigai, which I’m quite familiar with after having lived in Japan and having studied the language and culture there.

“It helps to assess what do you love? What does the world need? What can you be paid for? And what are you good at? And if it’s two of those things like for example… what are you good at? and what can you be paid for?–well then it’s a profession. What the world needs? and what can you get paid for?–It’s a vocation. What do you love? And what the world needs? Well, that’s a mission… and finally, what do you love and what are you good at? That’s a passion. But if you can actually put together [all four] the centerpiece of that Venn diagram overlap is this idea of Ikigai. Reason for being, or what I’d call life’s work.”

Finkelstein acknowledges that curating a career that fits into the idea of Ikigai is an incredible privilege, one that many of our ancestors would never have dreamed of being able to do. He tells me that he feels inordinately lucky to do what he loves for his career and changes people’s lives. I personally vibe with the idea of Ikigai, and it’s part of the reason that I’ve made some of my own career moves and pivots over the years. If you can love what you do and you’re good at it, why do anything else?

Using Entrepreneurship to Solve Problems

When it comes to his own experiences as an entrepreneur, Finkelstein says that he always used his entrepreneurial spirit to solve problems. He started a DJ company in his youth because he knew he couldn’t get hired by any existing DJ companies due to his lack of experience. He started his first Shopify store to help make money while he was sitting in Law School classes.

“I think what entrepreneurship is is being really, really reful,” he says. “Finding creative solutions to problems that you want to solve. So, I wasn’t necessarily overly intentional about it, but all of these little breadcrumbs I picked up like DJ-ing… [I asked myself] well, why do I like that? Oh, I understand. [It’s] because I can actually change someone’s energy; I can change their mood; I can give them something that maybe they didn’t know they needed and make their life a little better. Why have I devoted my life to Shopify? Because what Shopify is is effectively just giving people the tools that traditionally they did not have, and they use those tools to share their gift with the world. That lines up perfectly with my Ikigai. And how I redefine my purpose.

What actually is failure?

Finkelstein notes that being an entrepreneur isn’t always a path toward making millions of dollars. His own work with Shopify has exposed him to million-dollar companies like AllBirds or Bombas. Still, it’s also exposed him to smaller businesses comprised of people wanting to serve their communities because it gives them joy. He cites his own experience opening an ice cream shop with his wife in Ottawa–where he lives–because they felt that their neighborhood lacked a good ice cream parlor. He even talks about one Shopify store owner, Mike D from Durham, North Carolina, who started a BBQ sauce store to create a family business that his children could work with one day.

“It’s true, most small businesses do fail,” he says. “That’s doesn’t necessarily mean that you shouldn’t try because most small businesses fail. Just because I’m never going to be the fastest runner in the world doesn’t mean that I should never run. I get a lot of enjoyment out of running… It clears my head, it makes me feel good, there’s a lot of benefits to it. So, that definition of failure to one might be complete success to another… Success is a very individual personal thing, and if success for you is just, I’m gonna share delicious ice cream with my neighbors, then you can be a success and not make a million dollars.”


We’re living in a time where we’ve never needed to be more adaptable. The Covid-19 pandemic showed us how quickly the world, life, and our work could change. Humans never love change, and we tend to resist it, but when we can embrace it and re-position ourselves to succeed, not only can our business endeavors thrive, but we also thrive personally.

“When Covid hit, what we saw two different types of entrepreneurs, two different types of people,” Finkelstein says. “We saw folks that reacted by saying, alright, new information is in, I need to change some things around…so you saw some of these entrepreneurs and these people being really resilient. They saw this tidal wave and they grabbed their surfboard. But you saw others that are waiting for the status quo to continue. They didn’t grab the surfboard and surf when they saw the tidal wave, they ran to the shore and grabbed their towel. If you can be adaptable to any circumstance, any environment, regardless of what’s being thrown your way…you are going to be set up as a great human, because no matter what happens to you, you understand that you can react to it.”

Balance risk-taking with lesson learning

Finkelstein talks about how the risk level for trying out a business these days is much lower than it once was. Platforms like Shopify make it relatively simple for businesses to see if their new idea is feasible, marketable, profitable, etc… There was a time when a burgeoning or aspiring store owner had to rent out a storefront, buy insurance, hire numerous employees to come work shifts… they might have had to buy a certain level of inventory to fill the store shelves and open. Today with platforms like Shopify, Etsy, et al., entrepreneurs can start their business with much lower risk levels. The benefit I see in this is that people can try out different things before finding out what works best for them and what they love the most. Finkelstein says that failure is the successful acquisition of something that didn’t work. In other words, we learn from our mistakes.

“Entrepreneurship now is so much more accessible than it’s ever been. And technology is a massive catalyst for that,” he says. “The Internet is this new incredible city, in my mind, that is brand new, and it means that we’re all closer and we connect with more like-minded people and it’s so dynamic. So those examples of starting a brick-and-mortar store verses starting a digital store and being able to get information and pivot and adapt… it’s just the risk tolerance required is very different, which means that there’s no better time–maybe in the history of the planet–to be an entrepreneur than right now.”

More with Finkelstein here:

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About Tips Clear

Tips Clear is a seasoned writer and digital marketing expert with over a decade of experience in creating high-quality, engaging content for a diverse audience. He specializes in blogging, SEO, and digital marketing strategies, and has a deep understanding of the latest trends and technologies. Tips Clear's work has been featured on various prominent platforms, and he is committed to providing valuable insights and practical tips to help readers navigate the digital landscape.