Harley Finkelstein cites ‘special connection’ and ‘particular responsibility’ to Jewish community
“I know I’m never going to be the smartest guy in the room, ever. But I will be the guy who works the hardest.”
Harley Finkelstein is known for his hustle.
The 30-year-old entrepreneur has made his home in Ottawa as the chief platform officer (CPO) of Shopify, one of the fastest-growing tech companies in Canada.
“Hustle is just about persistence. It’s about being smart and creative.”
Finkelstein said his chutzpah was initially tested seven weeks into his first semester at McGill University in 2001, when his mother called from the family home in Florida with a message: “We are broke.”
Finkelstein’s father had been “leveraged to the hilt” and now owed creditors millions.
He was given a choice: leave McGill, go back to Florida and try to work everything out as a family; or try to make it on his own in Montreal, without any financial support and tuition costs of $18,000 per year.
He chose to stay in Canada.
“I needed to do something that would put food on the table and pay the bills,” he said.
“Most people become entrepreneurs out of passion, ambition. I wish that was the case for me. It wasn’t. That, to me, sounds so glamorous, so awesome. But, for me, it was disparity; it was having nothing.”
Out of desperation, with no money or experience, and very minimal equipment, Finkelstein launched a promotional apparel company to sell T-shirts to McGill.
Finkelstein eventually had a run of success during his undergrad years, which involved a transfer to Concordia University, which had more flexible scheduling to accommodate working students.
Challenges aside, Finkelstein – who moved to Ottawa in 2005 to attend law school, a move that threatened his T-shirt business – said he knew he had generations of history of the Jewish community from which he could find inspiration.
“We’ve all come here over the last 100 years and, in some cases, we’ve built the largest, most successful businesses in North America – we’re hustlers. There’s a real connection with the Jewish community and entrepreneurship,” he said.
“We’re a self-made people and we’re a survival people. The companies that I sort of look up to the most, a lot of them are run by Jewish entrepreneurs.”
It was Finkelstein’s weekly meeting with a small group of local entrepreneurs, including Shopify founder and CEO Tobias Lutke, which allowed him to save his T-shirt business and ultimately realize his life’s work.
Finkelstein took his business online using Shopify’s software and launched Smoofer.com, retailing licensed T-shirts.
Lutke later realized he wanted Finkelstein on his team at Shopify, and brought him onboard as CPO. Finkelstein said he couldn’t be happier with the result.
“Most people spend their entire life working a job to eventually retire and start their life’s work. What I’m saying is, find your life’s work as early as possible and do nothing else. Shopify and building businesses like Shopify, that is my life’s work,” he said.
“That’s really part of what I want to explain to students and younger entrepreneurs. They don’t have to believe me, they don’t necessarily trust me, but I do want them to at least have a different perspective,” he said.
Conventional wisdom that has typically come from school and parents, Finkelstein said, can be soul-crushing if a young adult chooses a secure career path simply for the sake of long-term security.
“Find something you love doing. To spend 40 years working a job and saving money, so when you retire you can start your life’s work? I think that’s backwards. I think we should start thinking about what our life’s work is right now,” he said.
“The Jewish community has always been very supportive of me and everything I’ve done. I’m not religious, but I’m very traditional. And, so, I give advice to a lot of people, but I feel a certain loyalty and a certain connection to the Jewish community.”
Shopify has hosted Shabbat at Shopify for Young Professionals, including medical, law and graduate students, where the Ottawa office offers its space
for the evening.
For an entrepreneur and CPO whose time is now his most valuable commodity, getting time with him can be a challenge, Finkelstein advised.
“What’s interesting is that people who really know how to hustle always figure it out,” he said.
“I feel a connection to all entrepreneurs and all young people, but I feel a special connection, and a particular responsibility, to help Jewish entrepreneurs and the Jewish community in particular,” he said. “I think that’s really important.”