“Knowledge is pain,” Harley Finkelstein told an audience of rapt 20-somethings as he perched cross-legged on the end of his chair in jeans and a T-shirt.
“In the early days, I had this misplaced sense of cockiness. I didn’t listen to people. Now I’m 33 and I feel like I know very little,” the native Montrealer, currently chief operating officer at e-commerce company Shopify, declared with the world-weariness of someone years his senior.
Finkelstein, who spoke Oct. 26 at downtown law firm Torys as part of the Disruptors Speaker Series hosted by Genesis: UJA Federation’s Centre for Jewish Innovation, has been working as an entrepreneur since he was 17.
He was interviewed by Jay Rosenzweig, founder of Rosenzweig and Company Inc.
Raised in Boca Raton, Fla., Finkelstein returned to Montreal to attend McGill University and, he explained, was hit in the first week of school by news that his parents were facing financial hardship and his father could no longer work.
“I was given an ultimatum: move back to Boca Raton to live with my parents, or stay in Montreal and fend for myself,” he said.
He chose the latter, and, after various attempts to find work, he started selling T-shirts to universities.
“My competitors would go in with pictures of T-shirts and I would print the actual T-shirts and show up with them already made. I’d say, ‘This is what you’re going to get from me.’ I made the process fun. I created mini-fashion shows in their offices. The guys that came in after me would be in suits and ties.”
It was this type of scrappiness that Finkelstein says got him where he is today and that he stresses is crucial to getting ahead in business.
“Today, access to capital has become almost easy. Every city and town has nine different accelerators, so in a heartbeat, someone’s going to give you $50,000, and I think, in many cases, it does a disservice,” he said.
Finkelstein went on to get his law degree and his MBA at the University of Ottawa, where he co-founded the JD/MBA Student Society and the Canadian MBA Oath.
He is also one of the Dragons on CBC’s online series Next Gen Den.
After law school, he did an articling placement in Toronto, describing the experience as the worst year of his life.
“Law is the antithesis of entrepreneurship. Entrepreneurship is all about meritocracy. The person with the best arm throws… In law, I was the articling student… they’d allocate work based on how long you’d been there.”
Finkelstein described meeting Tobias Lutke in Ottawa, the entrepreneur who started Shopify, and Finkelstein eventually moved to the city to help build the company, which in 2015 had revenue of $205 million.
In addition to his hardscrabble teen years, Finkelstein credits his raw ambition, penchant for networking and strong mentors for his success.
“I may not be smarter than everyone in the room, but I’m always going to work harder than anyone in the room… I’m ambitious… I have the kind of stress that makes me, when I wake up in the morning at 6:30 a.m., want to get out of bed because there’s so much I need to do… It’s a stress that manifests itself in ambition.”
As for mentorship, Finkelstein said he’s been able to “curate” a group of mentors throughout his life who advise him on all manner of things, from business to family life to investment decisions.
“People will meet someone who inspires them and go, ‘That’s my mentor…’ but mentorship means commitment, whether it’s a phone call once a month or a coffee once a quarter.”
With things having gone so well for him, he wants to give back, Finkelstein said, both to the Jewish and the start-up communities.
In addition to wanting to mentor young Jewish entrepreneurs, he’s become an angel investor in several companies and is on the board of a few venture funds. “The entrepreneurial and Jewish communities are the ones that have given me the most, so those are the ones I want to focus my time on.”