Some entrepreneurs start businesses out of passion, or a great idea. Not Harley Finkelstein. ”I always had a certain natural gravitation towards entrepreneurship,” he says, but maintains his introduction to entrepreneurship was a little less glamourous. “It was less about passion and more about necessity.” He was born in Montreal but grew up in Florida in the wealthy community of Boca Raton, and moved back to Montreal to attend McGill University after graduating high school. “I lived a bit of a sheltered life, and didn’t really know the value of a dollar, at least the way I do now,” he says. A few months into school his dad lost his business. “Effectively, we were broke,” he says. “I had two options. I either had to move back down to South Florida to live with my parents or stay in Montreal and support myself.” He tried part-time jobs but he didn’t want to interrupt his studies, and after speaking with a friend on student council who told him how much the school spent on promotional t-shirts every year Finkelstein got the idea to start his own t-shirt company.

Harley FinkelsteinHe scraped together enough money to buy a screen printing machine, and began printing t-shirts out of a small office that he was able to use for free. He managed to get local schools including McGill on board within the first few months, and by the end of 2002 he had five customers. Between 2002 and 2005 he continued to build the business, and the company grew to about 50 clients. He hired some staff that allowed him to spend less time in the office. “By the time I finished my undergrad the company was pretty much self-sustaining,” he says. He went on to law school in Ottawa with the idea that he would still run the company but with no day-to-day responsibilities. “Today my responsibilities are absolutely minimum,” he says, and while the company isn’t growing as much as it was in the early days it’s still operational. His company’s t-shirts are still worn by corporate clients including Beaver Tails, but 90-95% of the business is focused on selling to schools. Finkelstein says there were (and still are) advantages to working with schools. “The people making the decisions to purchase shirts weren’t necessarily the ones paying the bills,” he says. Also he was pitching people his age who understood where he was coming from. And he didn’t like how fickle corporate clients could be – whereas he knew schools would need an order every year, corporate clients would order from him one year and disappear the next. “Our sweet spot is really universities.”

His lessons during that first business really stemmed from the reason he started it. “Necessity is a major motivation,” he says. “That in itself was a huge driving force, and a huge catalyst for my success.” He also says he learned the importance of an entrepreneur being an extension of their brand. He says that clients trusted him because they could reach him at all hours of the day, and he was the ones doing the sales pitches. “It was really ‘well it’s Harley’s company, he’ll go above and beyond for us, we have his cell phone, if it’s Saturday night and we need shirts for Monday we can call him and we know that he’ll be in the office Monday morning printing t-shirts for us,’” he says.

Finkelstein’s latest business venture is also related to retail, but with an online twist. He joined Ottawa-based startup Shopify earlier this year as the director of business development, after striking up a friendship with the company’s founder Tobias Lütke at a local founders meetup. Lutke founded Shopify because it was too difficult to get an online store up and running – now the company is an online-retail platform bringing advanced commerce functionality to businesses of all sizes. The company currently has customers in over 60 countries, and processes more than $100 million in revenue for its over 10,00 clients, including Tesla Motors and General Electric. But while they may have big-name clients, the company is also focused on helping smaller retailers set up an online storefront quickly and easily.

Shopify also recently closed a $7 million round of Series A funding from Bessemer Venture Partners, FirstMark Capital and Felicis Ventures. Finkelstein says the company will use the money to expand internationally and focus on becoming a better-run company. “I know that’s vague, but the reason is that we really didn’t need the money,” he says. “The investment is more strategic.” He says the people who invested in the company are thought-leaders who can lend their expertise to the company going forward.

Finkelstein can point to a couple specific reasons why Shopify is so successful. “The reason we’re fairly successful is because everyone here loves what they do,” he says. “I am obsessed with this company.” He says in his opinion the idea of work/life balance is strange, because if you love what you’re doing it’s all just ‘life.’ “Your business is just part of that. If you can find something you love doing and do it every day you’ll be successful.” He says passion is really important at Shopify, and that while you can teach business acumen and technology, passion is a prerequisite as a startup. “I don’t wish anyone had to go through an incident like I went through when everything got turned upside down in my world,” he says. “But I have to say that experiences like that do make you stronger, it’s motivating. In one respect it was the worst thing that ever happened to me, but in hindsight it was the best thing that ever happened to me, and I wouldn’t be anywhere near where I am today without those experiences.”

This was a guest post by Erin Bury and was published today on the Sprouter Blog. Toronto-based Sprouter facilitates networking and collaboration between entrepreneurs globally.