An entrepreneur’s secret to success: hustle

Award winners’ stories show similarities

They are both lawyers who became entrepreneurs but on the surface, Wes Nicol and Harley Finkelstein don’t appear to have very much else in common.

For one thing, Nicol was born in the 1930s, whereas Finkelstein is just a few weeks into his 30s. Nicol is looking back on a long and successful run in the bricks-and-mortar world of homebuilding while Finkelstein is still near the beginning of a promising career in the digital space with rapidly growing Shopify.

Yet it was fascinating to note the similarities in their stories, not to mention their parallel passion for Ottawa, when they took turns speaking at the Best Ottawa Business Awards last week. Each earned a standing ovation for his inspiring words.

Nicol, the Tartan Homes founder who was honoured with the Lifetime Achievement Award, endeared himself to the crowd with talk of his childhood in Ottawa, when he began delivering groceries and selling newspapers to make a few cents at a time.

That’s how he paid his way through law school and set up his practice.

Then, seeing an opportunity in a growing city, he launched his real estate business.

Finkelstein, the Newsmaker of the Year, captivated the audience with his keynote speech.

For the first time, he shared the real reason he became an entrepreneur, reacting out of “necessity and desperation” to his family’s financial troubles when he was still a teenager. He launched a Tshirt business to pay his way through university.

For both men, it wasn’t the concept, but the effort and implementation that made the difference.

“Many of us have a great idea,” says Finkelstein.

“It’s those of us that execute and hustle that ultimately make it happen.

“I’ve had to become really comfortable with being uncomfortable. I’ve had to accept that rejection will happen 10 times more than getting a yes. I’ve had to sit with the idea that most people don’t want what I’m selling. And I’ve had to compete with those that have more capital, more resources, more connections than I do and still figure out a way to beat them. Ultimately I had to learn how to hustle.”

Beyond the similarities in their bootstrapped beginnings, it was clear that Nicol and Finkelstein share a genuine desire to see other people succeed and Ottawa thrive.

Nicol has long had an interest in young people just like Finkelstein. He’s donated millions to Carleton University, and for the past decade has financed the Nicol Entrepreneurial Award, a national business plan competition for university students.

Shopify has a similar passion for budding entrepreneurs and executives. For one thing, it employs a number of them. Finkelstein is one of only a handful of people at Shopify who remember the 1980s. It’s the kind of workplace from which future Finkelsteins will graduate to start their own companies.

In the meantime, though, Shopify is determined to hang on to as many of its growing list of employees as possible with an ambitious human resources strategy.

I talked to the parent of a new Shopify employee recently who was astounded at the benefits provided to employees — free lunches, biweekly home-cleaning and more.

Beyond that, Shopify has become a leader in the community of local startups. Finkelstein invites executives from other companies to the Shopify space in the ByWard Market to hang out and share stories and challenges. When you talk with him, it’s just as likely you’ll hear him promoting one of these other companies as talk about Shopify.

I’m struck by the fact that both Nicol and Finkelstein make frequent use of the word “hustle.” A few years ago, Nicol told me the secret to his success was that he never stopped working. “The hustle paid off,” he said.

For Finkelstein, the word has become a bit of a hashtag for his life.

He used it several times in his speech and it appears often in his musings on social media (I suspect the same would be true for Nicol if Twitter had arrived at a different time in his life). It’s not surprising that both men have an unstoppable industry about them.

But both also feel a deep connection to their community. Nicol says he chose to work in his hometown over Toronto despite the advice of friends at law school that he would be better off in the bigger city. “They were wrong,” he says.

Finkelstein, who moved here to go to law school, said having an “incredible local support system” has been a competitive advantage for both him and Shopify.

As an admirer of both men, it’s hard not to think it’s the city that is most fortunate, to have two fine examples of entrepreneurs who made something out of nothing, care deeply about their community and have blazed the trail for others.