One man proves that hustle pays off.

Harley Finkelstein - Ottawa’s No. 1 Hustler

Harley Finkelstein
COO – Shopify | Canadian Entrepreneur

I read an article in which you were quoted as saying “Today, entrepreneur is a state of mind.” What one piece of advice would you give to every entrepreneur?

It’s easier to get into entrepreneurship today than it’s ever been. Barrier to entry is super low. Anyone with passion and a laptop can start a business. But while the media may paint a picture of it being super sexy, and social-media-moviesque and all Mark Zuckerbergs building Facebook – entrepreneurship is still really tough. Failure rates for entrepreneurship are probably one of the highest of any profession.

If I could give one piece of advice, I would say that perseverance is really, really important.

Despite the fact that entrepreneurship may be a state of mind, and it may be something you’re passionate about, and it may be easier now than ever before – it’s still really, really difficult and perseverance is important.

Shopify has offices in Montreal, Toronto and Ottawa. These three cities have very different fashion identities. Which one do you identify with most?

Personally, I identify most with Montreal because that’s where I come from. That being said, I started Shopify as a lawyer coming from a big firm in Toronto. I showed up at Shopify on my first day in a suit and tie and very quickly, my attire went from a 10 to a 2 in formality.

Today, I find myself wearing jeans, sneakers and a t-shirt every single day. It’s my uniform.

You started a t-shirt business when you were in University. How did you come up with the name Smoofer?

I had a friend named Mike Smith whose nickname was Smoof. When we were sitting in class thinking of names for the business, he was there with us so we decided on Smoofer. At the time there were a lot of companies like Zappos, Google and Twitter who came up with names that didn’t really mean much. We thought Smoofer was kind of cool and had a personal connection for us – but more importantly, the .com was available.

I’m assuming you must have a massive collection of t-shirts – which is your all-time favorite?

Right now, I’m almost exclusively wearing James Perse t-shirts. For a long time, I was wearing American Apparel t-shirts, mostly because I had so many samples from my days in the t-shirt industry, but today it’s James Perse.

I’ve read and heard from many people that Shopify has a very unique work culture. I loved the “hustle your way in” job posting – brilliant idea. How would you describe the Shopify culture in three words?

Passionate, chaotic and fluctuating.

Passionate in that the people here are very passionate about what they do. This isn’t a job for them, it’s their life’s work. It’s chaotic in terms of the fact that we embrace chaos here. Whether it’s Shopify putting out a new product or starting a new marketing campaign – we like chaos. We’ve gotten really comfortable with being uncomfortable. Third of all, we’re constantly in flux.

This is a culture of change.

If you’re not changing what you’re doing on a daily basis at least once a month, you’re probably not doing the right thing. I don’t think our culture is about having two chefs, or giving everyone housecleaning, or having a slide. I think those are just perks of the office. Our culture is the aggregate of 425 personalities.

You started a DJ business in your early teens. If I were to take a look at your current playlist – what type of music would I see?

Right now, you’re going to see a lot of James Taylor and a lot of Crosby, Stills, Nash & Young. Paul Simon as well. On a normal basis, you’ll see a lot of eclectic music from the new Drake album, to things like old-school hip hop – I’ve been listening to the re-released Best of The Notorious B.I.G. album. But right now, I’m on a bit of an old-school rock kick.

How would you define your personal style?

I would say utilitarian. I like wearing jeans, t-shirts and sneakers everyday, but I want to have the best, most comfortable t-shirt, and the coolest pair of jeans I can find, and the nicest pair of sneakers. I’m very loyal too. Once I find a brand I love, I’m going to stick with it. It’s the same with the car I drive – I’ve found a type of car I like, and I’ll probably be driving it for the rest of my life.

Whose male celebrity style do you like most?

It’s the first time I’ve ever been asked that question. I don’t know too many celebrities, but I think in some American cities they try too hard. I wouldn’t do well in New York because you have to wear a buttoned-down shirt with a v-neck sweater on top and a sport coat – I don’t have the patience to do that. I think in California, there are a lot more laid back styles. Distressed jeans, sneakers and jeans seem to be big there, so I would fit right in. But I don’t have one favourite male style.

Some men collect watches, jerseys or baseball caps. Do you collect anything?

Things that say “Hustle.” Also things that inspire me, like artwork. I don’t have one particular obsession, but I like nice things. I don’t want to have 10 watches. I prefer to wait until I can afford that one watch that I really, really like. To me, quality always trumps quantity.

Finally – what is your favorite quote?

Discipline is remembering what you want.

Many of us are very passionate and excited about many different things, but really, to be disciplined is to remember what you want and keep focused on that. It’s one of the reason I write so many things down – I want to make sure I’m always focused.