I was heading to the opening of Jimmy's Coffee newest location: 100 Portland. When I got there the coffee shop was humming with activity— busy for an opening day.

I was meeting Ryan Maloney, the Director of Operations for Jimmy's Coffee. Ryan had been managing the day-to-day operations for the last two years ago and I wanted to find out what it took to run an independent coffee shop in Toronto— which, as he framed it, is "one of the most competitive coffee markets in North America."

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Above: Patio at Jimmy's Baldwin Street location.

My first impression of Jimmy's Coffee was when I moved to Queen West a few years ago. I began to see Jimmy's iconic yellow coffee cup everywhere. The yellow is unusual and stands out— you can spot it from across the street.

I always assumed the cup was a clever branding touch— but Ryan says the origin is unclear, "some people believe it was an intentional choice and others believe it was by accident." If it was by accident, it was serendipitous.

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Above: The iconic yellow cup.

Jimmy's got started when the founder, Phil Morrison, bought an investment property near Portland and King in 2009. At that time the property was "literally a crack house" and Phil wasn't sure what to do with it. So he thought, why not start a coffee shop?

He thought about naming the shop after Jimmy Carter before a friend convinced him that basing it off one Jimmy was too specific. Instead it would become Jimmy's Coffee as an homage to all famous Jimmy’s. (Pictures of Jimi Hendrix, Jimmy Fallon and Jimmy Kimmel adorn all locations.)

The first Jimmy's Coffee happened to be in the right place at the right time, "King West was developing as a neighbourhood and people flocked to Jimmy's for an urban experience... and away from that corporate environment."

From there they've continued a steady expansion within the downtown core— with an eight location in Etibicoke opening this fall.

LEFT: Baldwin Street location. RIGHT: Front Street location.

LEFT: Portland Street location. RIGHT: Mccaul Street location.

Ryan says, "any place you can get a coffee is competition." Which, when you think about it, is a lot of competition: Starbucks, Keurigs, McDonalds and the countless independent coffee shops across Toronto.

So how do you compete?

Location is one critical element. Ryan explains, you need "offices around you, retail to draw people to the neighbourhood and a backing of residential."

Of the three, office is most critical. "Most people get to their office, drop their stuff off and then go get a coffee. You really need those people working near by."

You also have to have proximity to your customers: "we don't sit in a board room making decisions, we rely on seeing what resonates with our customers." This means that often the best ideas "bubble up from managers, baristas or customers themselves."

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Above: Jimmy's Queen West location.

When you visit Jimmy's Coffee, Ryan says you should "have an interaction more than a transaction." The difference between an interaction and a transaction is ambiguous. It's hard to put your finger on it— but that doesn't mean it's not real.

The way to enable positive interactions is people— full stop. For Ryan, the ideal Jimmy's barista "likes to talk to people and have fun with customers." Though Ryan is quick to add that it's not just intense extroversion, "it can also be someone respectful and polite."

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Above: Ryan Maloney, Director of Operations for Jimmy's Coffee

Because people are so critical to Jimmy's success, Ryan works hard to take care of employees.

For example, managers have a chance to build up complimentary skills by doing things like running social media or photography. Twice a year Jimmy's runs have a company-wide competition where barista's compete to develop their speciality drinks. The winners get cash prizes and (often) a spot in the seasonal menu. Full-time workers also have health insurance.

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Above: Interior of the Ossington Street location.

But of course, the drinks also have to be good for a coffee shop to succeed. I asked Ryan if their lattes were better than Starbucks and he immediately responded confidently, "oh yeah."

He admitted he's certainly biased, "but when it comes to Jimmy’s lattes, our grind is a high priority and so is steaming of the milk... milk scalds easily." Ultimately what it comes down to "is a passion and technique at Jimmy’s that can’t be matched at big companies."

Story by Steve Benjamins & Photos By Jimmy's Coffee · Published July 5 2018