The next big move for Shopify president Harley Finkelstein? Montreal

Harley Finkelstein’s bio includes a number of descriptors: Shopify president, entrepreneur, lawyer, husband, father, mentor, prolific traveller, philanthrope, and part-time podcast host. Come August, it will include one more: Montrealer.

It’s safe to say the president of Canada’s leading one-stop-e-commerce company — powering millions of businesses in 175 countries, with a current market value in the billions — can choose to comfortably live anywhere in the world he wants to. Turns out that what he wants is Montreal. Finkelstein will soon be moving back to the city he was born in with his wife and two young daughters. Speaking with him is speaking to someone who’s very enthusiastic about… well, pretty much everything!

“My wife and I were born in Montreal,” he says. “I was raised in South Florida, returned to Montreal to attend McGill University, moved to Ontario and have been living in Ottawa ever since, building our company.”

While Finkelstein says he and his wife enjoy living in Ottawa, they always felt like something was missing. “As we began to think about where we wanted to raise our four- and seven-year-old daughters it became clear that it wasn’t there.”

Community and culture: Why Montreal won 

Finkelstein says three cities made the Top Three as possibilities on their list. Miami, because he grew up there and still has many friends there, New York City, because he’s there twice a month for work and loves it, and finally Montreal. The couple spent about three to four weeks in each of these cities last year understanding what it would feel like to live and work there.

“Ultimately, Montreal won,” he says. “And it won for two main reasons: culture and community. I once read that, ‘If you want to understand the trajectory of culture in a city, look for where the artists, the musicians, and the chefs are.’ If you see a city with a disproportionate number of artists, musicians and chefs that’s probably a city with great culture. Miami and New York have that, but Montreal has that in spades.”

The second winning element, he says, was community. “People are supportive and look out for one another in Montreal and even though I haven’t lived there in many years, it still felt like home to me.”

Finkelstein’s decision to move to a place that best corresponds to his and his family’s priorities also mirrors his company’s modus operandi. A few months after the pandemic hit, Shopify decided employees could work from anywhere in the world. Company CEO Tobi Lütke would later confirm the change, tweeting “office centricity is over.”

Finkelstein refers to this new normal as being “geographically agnostic,” and says it’s what makes their digital company so competitive in attracting the best talent. 

“The companies that are most innovative are very understanding of the fact that people want to live where they want to live,” he says. “We have thousands of people who work at Shopify, and we don’t really care where you’re based. It’s not necessarily a remote model or a hybrid model, it’s a model of choice. If you want to work at Shopify and you want to live in the country, or L.A., or Toronto, we want to embrace that because it provides us with an unbelievable amount of talent optionality where anyone in the world can come and work with Shopify.”

Finkelstein is now, too, choosing to move back to the city where his family is still based, and where he first tried his hand at being an entrepreneur.

“When I was 17, I moved back to Montreal to attend McGill,” he says. “My family fell on some really hard times, so I built a little T-shirt business to support myself while in school.”

He set up in Montreal’s famous garment district, right by Chabanel, selling T-shirts to universities for their orientation weeks and bookstores. 

“There’s this little underground coffee and sandwich bar called Gentile,” he says. “I used to go in there and listen to people like Sal Parasuco and David Bitton from Buffalo Jeans, these old iconic entrepreneurs talking about the schmatta business and the textile industry. Just being around them… there’s this residue of entrepreneurial energy that just oozes out of Montreal and exists there.”

When Finkelstein started selling his T-shirts online, he became one of Shopify’s first customers ,and after meeting with the company’s founder and CEO at an Ottawa coffee shop, he was hired soon afterwards. The rest, as they say, is history. Since 2020, he’s been the president at Shopify.

How immigrants shaped the city

Finkelstein says Montreal is the perfect city for those who have business in their blood and believes the city’s immigrants have a lot to do with that. “I don’t think there’s any city in the world that is more entrepreneurial than Montreal,” he says. “So many immigrants moved here in the last 80 to 100 years, including my own family who emigrated from Eastern Europe after the Holocaust in 1956. There’s so much small business, so much entrepreneurial activity here. I just recently gave the keynote at Startup Fest in the Old Port, and it was packed.”

Finkelstein believes there are essentially two types of entrepreneurs: passion-based entrepreneurship and entrepreneurship based on survival. “These entrepreneurs fundamentally have no choice,” he says, “they have to go into small businesses because nobody is going to hire them. And that’s essentially my family’s story when they first moved to Montreal.” 

Finkelstein’s grandfather opened a little egg stall at Jean Talon Market, le Capitaine, which is still there today and now run by his uncle. “It was entrepreneurship by necessity,” he says. “My grandfather was not especially passionate about eggs. He was passionate about survival. He came to this country with no money, didn’t speak the language, had no education. But then, once he started doing it, he became the egg guy at Jean Talon Market, and he was the egg guy until he passed away a few years ago. A lot of people in Montreal are doing what they consider to be their life’s work. And that is very different from having a 9 to 5 job.”

As the grandson of Holocaust survivors, Finkelstein says he wants to give back to Montreal’s Jewish community, but also the city as a whole. 

“My wife and I want to get involved philanthropically,” he says. “It matters to us. Every single community makes this city better and so much more interesting. The Jewish community, the French community, the Greek and Italian communities, etc. The key is to bring it all together with this understanding of mutual respect and enthusiasm for everyone’s culture. The more colour we have, the more vibrancy we receive. You don’t want everyone wearing the same basic thing, listening to the same basic music, eating the same basic thing. The world is more interesting when you bring more voices rather than fewer voices.”

As he prepares to make the move back to his hometown, Finkelstein welcomes feedback (@harley on Instagram. His DMs are open) and says he’s eager to help shape the city’s narrative. 

“This is personal to me,” he says. “I’m not just moving to Montreal for my work. I’m bringing my kids, my wife, we’re all coming there, this is going to be our new home. If you want to have a great city, I think every single person who lives in the city has a responsibility to figure out a way to help promote that city.”

‘Something in the water’

Finkelstein has no doubt that immigrants who found a home in Montreal have contributed to shaping the city’s entrepreneurial spirit. 

“They created role modelling for future generations to say, ‘If you’re actually creative and ambitious, entrepreneurship may be a wonderful thing for you to pursue.’ That is very different from cities where the primary industry is finance or bio-tech. You have more people taking more risks. You have this default-to-yes mentality here.” 

Wanting to speak with some of these titans of industry himself, Finkelstein started a podcast called Big Shot with David Segal, the founder of David’s Tea (another Montreal start-up) and the largest Canadian-based specialty tea boutique in the country. 

“David and I sat down with people like Charles Bronfman, who brought Major League Baseball to Canada, Aldo Bensadoun, who created Aldo Shoes, Jonathan Weiner from Canderel, Issy Sharp from Four Seasons Hotels. All of them have deep connections to Montreal,” he says. “Aldo came to Montreal with nothing and built this billion-dollar empire.”

Finkelstein believes successful people here want to be the best at what they do, not just in Montreal, but on a global scale. “They just happen to want to do it from Montreal.”

Finkelstein also credits ambition as a major driver in the city. “Guy Laliberté doing tricks in Old Montreal and then building this global empire with Cirque du Soleil?’ You have quality of life and creativity here, but you also have deep ambition.”

Immigration, he says, is a major source of ambition and he applauds government efforts to increase immigration in the country. “More immigration is a good thing,” he says. “We’re bringing in people who are ambitious, who are talented, who want a better life for their families.”

He says he’s been fortunate to have incredible mentors in his life who’ve helped shape his career. “A disproportionate percentage of those mentors are either from Montreal, or live in Montreal,” he says. “People like Stephen Bronfman. Mitch Garber, Leonard, and Anik Schlemm. It seems like there’s something in the water here. So, let’s invite more people to see what’s in the water in this city.”

An enthusiastic ‘Oui, oui’ to French 

As a soon-to-be Quebecer (again), Finkelstein admits he’s not yet fully bilingual but is happily embracing the challenge of learning French. He doesn’t see it as an impediment but as an opportunity and an asset. 

“If we can put aside some of the tension regarding French versus English and tone down the rhetoric a little and just say, ‘If you’re going to live in Quebec, you really should learn to speak French. It’s important and it’s going to be valuable to you.’ I think that conversation is far better than, ‘If you live in Quebec, you must do this and must do that.’ 

Finkelstein says he’s embracing the challenge and wants to eventually be able to present at least half of a future keynote speech in French. “I can’t do it right now,” he adds, “but it would be really cool if in a year or two I’m proficient enough that people can understand me.”

Rather than a point of contention, he thinks French should be embraced.

“Talented people are moving here and they’re coming notwithstanding the fact that there is some uncertainty regarding language laws, but the truth is that French actually makes Montreal more compelling and interesting because you have different cultures and different languages spoken here.”

Finkelstein believes Montreal should embrace the fact that it’s a bilingual city and use a carrot to promote French and not a stick in the form of laws and legislation. “I think we actually need to pivot to the carrot because I think that’s where you’ll get a lot more results.”

As far as linguistic tension goes, Finkelstein believes it’s a very simple ‘solve’: mutual respect. 

“If I walk into a café and I hear people speaking French I will say, ‘Je voudrais un café avec de la glace.’ I’m sure my accent sucks, I’m sure it’s not exactly how you ask for a coffee, but the woman behind the counter understood. There was an immediate change in dynamic because she immediately saw that I’m not francophone and I obviously don’t speak French that well, but she appreciated the fact that I was putting in the effort. And I did that because it felt like the right thing to do. It felt respectful. It felt like something that would lead to better engagement.”

Why Montreal’s future could be very bright 

As more and more people are going to have the choice of where to live, Finkelstein believes Montreal has the opportunity to become one of the most important cultural hubs in North America. 

“Historically, large cities had exclusivity on the best jobs,” he says. “If you wanted to get a big job at a particular bank or company, you had to move to the city. Post COVID, there’s way more flexibility. ‘Digital by design’ means you can live anywhere you want to and still work in a company of your choice.” 

According to Finkelstein, that means that every single city in North America is now on the table and people are being a lot more thoughtful about where they live.

“Many people are now thinking, ‘Where can I live in a place that inspires me?’ Alexander Chalmers wrote there are three tenets of happiness: ‘Someone to love, something to look forward to and something to do.’ I believe there’s a fourth one, and that’s being in a place that deeply inspires you. I’m on the road probably 100 days a year for work and I’ve been to every major city, and there’s something about Montreal that is so deeply inspiring, and it has nothing to do with the fact that I’m from there, or that I have friends and family there.”

Finkelstein believes the work-from-anywhere model presents as a major opportunity for a city like Montreal. 

“Every city has issues,” he says. “But Montreal has the chance — specifically in North America, if you want a particular lifestyle and culture and you have more optionality about where you’ll live — in the next decade, to probably be one of the most interesting cities you can live in on the continent.”

Finkelstein believes the city should be louder about what makes it so special. “We need to tell people about what’s happening here,” he says. “I can’t wait to bring friends of mine who are also tech entrepreneurs from around the world and show them the Tam-Tams on Sundays on the mountain, the late-night restaurants, bring my children and their friends to Piknic Électronik. We should celebrate the things that make us unique and not take them for granted. I know I’m new here and it’s all still shiny, but I’m choosing Montreal over pretty much every other city on the planet because I think it’s the best place for me to be.”

He’s not the only one who feels that way. “Random friends of mine are now calling to tell me they’re also moving to Montreal. The city has some swagger. It’s not for everyone, but for a particular type of person, there’s nowhere in the world like it.”

A good time to take a chance 

Finkelstein may have a BA in Economics, a Law Degree and an MBA, but it’s clear when talking to him that his one true passion is entrepreneurship.

The businessman, who’s made it on Canada’s Top 40 Under 40 and serves as mentor and advisor to various organizations and incubators, believes that right now is one of the most interesting times to start a business.

“I think entrepreneurship is the greatest thing in the world,” he says. “It allows you to create something, build something, and then share it with everyone. I don’t think there’s any better way to spend your time.”

And now, he says, is a very good time to jump in.

“In this new era of business creation, the cost of failure is as close to zero as you can get,” he says. “Tinker on things, play with different ideas, try new stuff. If people like it, they’ll tell you. If they don’t like it, they’ll also tell you.”

Finkelstein says people often get discouraged because they don’t see what happens before the success. 

“You only hear about people’s highlight reels,” he says. “You hear about Shopify, but you don’t hear about the eight different companies I started when I was in Montreal that completely failed. The poker-chip company that didn’t do very well. A slipper company that completely failed. I think aspiring entrepreneurs look at the successes and think, ‘Well, they just hit it out of the park, home run.’ No. Every successful entrepreneur has a past that is littered, littered with failure.” 

The best entrepreneurs, Finkelstein says, are resilient enough that they don’t lose any enthusiasm or ambition as those failures mount up. “If you can actually have a failure and come back to the next one with the same enthusiasm, the same spirit and ambition as the previous one, you end up winning.” ■

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Read more weekly editorial columns by Toula Drimonis.