Philip Rimer remembers offering some fatherly wisdom to Harley Finkelstein when his young protege told him he wanted to pursue a career in business rather than the courtroom.
Harley Finkelstein is the chief platform officer for Shopify.
By David Sali
“My advice to him was to really think hard before he left law,” says Mr. Rimer, one of the city’s top real estate lawyers, of that conversation more than four years ago. “Once you make that jump (out of the legal profession) … it’s difficult to get back in.”
Mr. Finkelstein, he notes with a chuckle, “considered and dismissed” his counsel.
After all, there’s never really been much doubt where Mr. Finkelstein’s true passions lie. If the label “born entrepreneur” fits anyone in town better than the chief platform officer of the capital’s hottest company, Shopify, no one’s found him yet.
But Mr. Finkelstein showed a much different side of his personality at the Best Ottawa Business Awards in late November, when he shared with 600 captivated listeners the real story of what fuelled his first commercial success.
Seven weeks into his first semester at McGill University, Mr. Finkelstein, then 17, felt like a big man on campus, driving a brand new car and living in a fancy apartment. He “had life by the horns,” he told the crowd.
Then one day, his mother called with three words that turned his world upside down: “We are broke.”
His father was bankrupt and owed millions to creditors. Mr. Finkelstein was left with a tough choice: he could either return to his family in Florida or stay in Montreal and fend for himself. He stayed.
“I had to do something drastic,” he said.
For a while, he worked at a cafe and a travel agency, struggling paycheque to paycheque. Then a friend on McGill’s student council told him there might be money to be made selling T-shirts to the university. Mr. Finkelstein bought a cheap screen printing machine and started calling everyone on the council’s executive every morning at 9:30 sharp.
“Maybe that was harassment,” he told the audience. “I didn’t care.”
His persistence paid off. He soon landed the contract to supply the university with 200 T-shirts, delivering his first order three days early. He threw in an extra 20 shirts for good measure.
“That changed everything for me,” he said.
Three years later, he was supplying apparel to 50 universities across the country.
“I learned more from that experience than I have from anything else in my entire life,” he said.
What he learned has become his mantra, and a frequent hashtag on his many tweets: hustle.
“Many of us have a great idea,” Mr. Finkelstein says. “It’s those of us that execute and hustle that ultimately make it happen.”
Mr. Finkelstein’s friends knew of his early struggles, but he’d never talked about them publicly until that night at the BOBs, when he was honoured as Newsmaker of the Year.
“That was me as vulnerable, I think, as anyone has ever seen me,” says the 30-year-old Montreal native. “I really started my first business not out of passion, but out of necessity and desperation. But that being said, I always had some entrepreneurial ambitions in me.”
Those ambitions go all the way back to his early teenage years. At 13, an age when most enterprising teens’ idea of a money-making venture would probably be a paper route, Mr. Finkelstein went to a bar mitzvah, where he watched a DJ work the crowd into a frenzy.
Or rather, everyone else saw a DJ. Mr. Finkelstein saw a business opportunity.
Soon, he was hauling sound equipment to parties and bar mitzvahs on his bicycle and convincing buddies to assist him. It wasn’t a lucrative venture.
“We made no money,” he says with a laugh. “I don’t think we were a very good business, but early on it did teach me about things like customer service, things like being responsible. At 13 years old, you have an event on (Friday) night, for example, if you’re in school all day long, you have to be very effective with your time.”
The lessons he learned in those early days have served him well ever since. Mr. Rimer, who calls Mr. Finkelstein “the son I never had,” says his longtime friend’s “drive and focus” are his greatest attributes, and rarely have they been as evident as in his days hocking T-shirts and struggling to help keep his family afloat.
“I really did a degree in T-shirts,” he says with typical candour. “I was doing an economics degree, but I very rarely went to class. I wasn’t the model student, because frankly I was spending most of my time on Chabanel (Street, Montreal’s garment district) in my office printing T-shirts. My focus for that period between when I was 17 and 21 was really all about survival.”
After finishing his degree at Concordia, which was more willing than McGill, he says, to accommodate his career as a budding entrepreneur, he moved to the nation’s capital in 2005 to do a joint law degree and MBA at the University of Ottawa.
A serial networker, Mr. Finkelstein did some digging and soon found out about a coffee shop in the Glebe where some of the city’s brightest young business minds hung out. What happened next would ultimately change the face of Ottawa’s high-tech sector.
“I showed up there and I got a chance to meet a bunch of these entrepreneurs, and one of them was Tobi,” he says.
A programmer by trade, Tobias Lütke was in the midst of transforming an online snowboard shop into the groundbreaking enterprise now known as Shopify. Mr. Lütke had written software to provide an inexpensive, easy-to-use virtual storefront for online businesses, and was looking for customers.
“The timing was right,” says Mr. Finkelstein. “Here was this brilliant, brilliant programmer whom I really liked and really respected and truly I was inspired by in many ways. And I needed a business that was more virtual.”
He became one of Shopify’s first customers, selling T-shirts online using Mr. Lütke’s platform.
“That was the first time I was sort of able to get a glimpse of what I thought the future of retail might look like,” Mr. Finkelstein says. “Frankly, I was excited by it. I thought it was democratizing. I just thought that this was the most exciting thing I had ever seen.”
After completing his law degree and MBA, he spent a year articling with a big Toronto firm. The dynamic, hustling Mr. Finkelstein and corporate law were not exactly a match made in heaven.
“To be honest, that was one of the most difficult years of my life,” he says. “That was the year I realized I truly am an entrepreneur, I want to be an entrepreneur. I found that practising traditional law in a law firm in downtown Toronto, it was a very risk-averse profession. And frankly, often as an entrepreneur, you have to take risks – calculated risks, of course, but you have to take risks.”
He returned to Ottawa and had a chat with Mr. Lütke, who had decided he’d had enough of the ultra-demanding Mr. Finkelstein as a client and wanted him as a co-worker.
“To be honest, he was the biggest pain-in-the-ass customer ever,” says Mr. Lütke, who’s become one of Mr. Finkelstein’s best friends and mentors.
“He always tried to get an even better deal on Shopify, so I essentially made his account free at some point so he would stop calling me. I thought, ‘Wouldn’t it be great to have that bundle of energy working for me rather than against me?’ Harley agreed and joined Shopify to run business ops and our platform team.”
At the time, Shopify had fewer than 20 employees, most of them website developers and designers.
“You had incredible hackers there,” Mr. Finkelstein says. “I guess I was one of the first hustlers that joined the company. As they say, the rest is history.”
Today, they are a superstar team, the Lennon and McCartney of Ottawa’s startup scene. Shopify, which has more than 320 employees, was named Canada’s third fastest-growing tech company in a recent Deloitte survey. Its platform serves more than 75,000 customers in 100 countries, including heavy hitters such as Budweiser, Gatorade and General Electric. The firm has offices in Montreal and Toronto in addition to its headquarters in the ByWard Market.
Shopify was one of the first high-tech outfits in Ottawa to set up shop downtown, away from Silicon Valley North’s traditional Kanata hub. That decision helped give the company a funky, hip vibe that fits the lifestyle of Shopify’s youthful workforce, Mr. Finkelstein once said, and sparked a tech renaissance in the Market.
Defying conventional wisdom is just part of Mr. Finkelstein’s DNA, say those who know him well.
“He and Shopify very much epitomize having to do things differently to have some success,” says Kanata lawyer Debbie Weinstein, who employed Mr. Finkelstein as a summer student when he was at the University of Ottawa. “If you really want to be successful, it probably means cutting some new cloth. And to do that, you’ve got to be a little different. And you’ve got to be pretty innovative.”
Never one to rest on his laurels, Mr. Finkelstein is pushing the company further into new territory. Earlier this year, the firm launched Shopify Payments, which allows merchants to process credit cards without a third-party payment gateway. It has also created a point-of-sale app that allows merchants to keep track of in-store sales and inventory and run online storefronts on an iPad.
“The truth is that magic happens when you step outside your comfort zone,” Mr. Finkelstein says. “We do a lot of experimenting. We try something out. If it works, we scale it. If it doesn’t work, we acknowledge that and perhaps we move on.
“For many of us, this is our first rodeo. So we don’t have scar tissue from previous experiences saying, ‘Well, you can’t do that.’ That’s not how it is. We’re just doing what feels right to us. We make a lot of mistakes, but we learn from our mistakes. And if you’re not making mistakes, you’re probably not running fast enough.”
But as driven as Mr. Finkelstein is, his friends also describe a generous man whose door is always open to aspiring entrepreneurs and who gets as much of a kick out of their successes as his own.
“He’s a very easygoing, friendly, yet direct kind of a guy. He’s a very complex person. For a kid his age, I could learn things from him. He’s ambitious, yet sincere,” says Mr. Rimer.
Mr. Finkelstein, who married his longtime girlfriend Lindsay earlier this year, doesn’t stop at pushing boundaries in business. He also recently began exploring an artistic side he never thought he had.
“In September, I decided that I wanted to take a course in something that I just knew that I was not going to be good at with people that I don’t really know, so I took a pottery class,” he says. Next month, he starts guitar lessons.
It’s all part of his guiding philosophy: if you’re sailing along on smooth seas, it’s time to steer into uncharted waters.
“In the same way that I put myself in uncomfortable positions professionally, I also try to do that personally,” he says. “I think that makes me more well-rounded. It reminds me that there’s so much more to life that I have to learn.”