The Next Generation of Skiis & Biikes


words :: Colin Field

When Paul Montgomery started the Caledon Pro Shop back in 1978, he couldn’t have known all the challenges that were coming. His timing was spot on though; ski shops and outdoor shops were popping up all over the place.

But a ski shop wasn’t a license to print money; lots of hours and hard work went into Montgomery’s success. With an emphasis on service and a mission to get families outside having fun in the winter, he soon found his loyal clientele.

Paul Montgomery in his original shop at the Caledon Ski Club. October 2, 1978.

In 1986 Montgomery opened his flagship store in Mississauga calling it Skiis (with two ii’s so he could trademark the name). To support the store through the summer months, he started selling bikes too, his other favourite sport. The store officially became Skiis & Biikes in 1988. The company continued to expand; a Collingwood location in 1996, a Don Mills location in 2002.

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“Being self-employed comes with unique hurdles,” says Paul. “In 1980, a month before Christmas the store burned to the ground. Five days later we re-opened it in the living room of my tiny house. With the help of dedicated staff and loyal customers within a year we were back to normal. Years later on Christmas Eve we had a pipe in the Mississauga store break and it flooded the store. We worked until early Boxing Day morning and opened on time.  Most of the staff and all the customers just noticed how clean the carpets were, they had no idea what had happened. Then during the massive ice storm in Toronto in 2013, when the power was off for days over Christmas, we remained open with staff-issued headlamps and wearing ski jackets to stay warm. We continued to help our customers get their Christmas shopping done and equipment serviced. During these moments you wonder how you’re going to cope, but after you dust yourselves off and pat each other on the back, you say, ‘We avoided that disaster.’ We look back at these moments as builders of the company.  Customers are loyal to us, we have to be loyal to them and don’t just close the doors because things get tough. No matter how tough it gets, you regroup, create a plan, roll up your sleeves and execute the plan.”

In 2008, following the old adage, “go west young man,” Paul’s son Devin headed to Whistler where he opened a new shop at Creekside in 2008. The McGill business school graduate saw it as an adventure and was up for the challenge. Paul had always dreamed of having a shop in Whistler. So much so they acquired two more shops out west in 2009, one in Whistler and one in Vancouver. But this is where the biggest challenge began.

1987. Fancy tuning gear at the fancy Mississauga flagship store and the first of the Skiis & Biikes shops.

“By 2015 we were in a pretty desperate situation,” says Devin of the BC shops. “We had three stores in BC and this is after purchasing over a million dollars of tuning equipment and trying to integrate staffing into the business and deal with all that growth. On top of that we had two pretty bad winters; in 2013, 2014 there wasn’t a lot of snow, not a lot of confidence in skiing. Pair all of that with a real estate market that shot up out of nowhere, especially in retail rentals, and we had a perfect storm that just really tested the business’ limits.”

“I didn’t research Whistler enough,” adds Paul. “Margins in Whistler and Vancouver were lower than even in Ontario. Wages were higher and the staff pool was challenged. Rents were 10 times higher than Mississauga. It was an impossible situation. We are not quitters but there was no light at the end of this tunnel.”

But for the Montgomerys, adventure is in their genes.

“We were basically on the ropes,” says Devin. “We sold the assets in Whistler, and did not renew our lease in Vancouver. Then in 2017 I moved back to Ontario to help rebuild our foundation.”

“Do I regret opening Skiis & Biikes in Whistler? No,” says Paul. “I could have done it differently, maybe, and been somewhat successful, but the resort has all the cards and independent shops are at a huge disadvantage. I’m glad we tried as we learned a lot and made a lot of friends, had a lot of experiences and adventures. Devin learned the difficulties of running his own shop. For me, it was always my dream, so now on my deathbed, in about 35 years, I won’t be saying, ‘if only I had opened in Whistler.’”

After the original shop was destroyed by a fire, Paul Montgomery worked in this A-frame for a number of years at the Caledon Ski Club. Fall 1981.

Back in Ontario, Devin’s younger sister Gillian had joined the company too.

“Gill’s value to the company comes from analytics, operations, ultra-organized and she has an MBA,” says Paul. “Devin’s strength is creative digital marketing, HR, plus he’s a good boot fitter.“

Back in Ontario, Devin, Gillian, and Paul divided up the jobs based on strengths and started attacking.  

“My strength was 40 years in business, so I know and have dealt with all the credit managers and presidents of all our suppliers,” says Paul. “I went to work to buy us time and increase margins. Gillian streamlined our systems to be more efficient. Devin did his marketing magic, created great teams and built the web site.”

With Paul at the official retirement age of 65, Devin and Gill are poised to take over the business.

“We’re trying to entice him with travel and things like that,” says Devin. “He just has so much passion for the shop that he built. He gets so much joy from outfitting families. He’s still in the shop. I think maybe semi-retired is what we say right now.”

The family that skiis together; Paul, Gillian and Devin Montgomery enjoying some quality family time and some Japow.

Businesses have lots of hiccups. This one has only made the family and the business stronger.

“We weren’t prepared to expand that quickly into a market that we didn’t know,” he says. “It’s a huge gift to be able to survive from a mistake that large and to have that experience, especially as a person in business and an industry where a lot of mistakes take people out.”

So as the managing partners Devin and Gillian Montgomery slowly take over the business from their father, they’re thankful for the opportunity and have refocused on what’s important for Skiis & Biikes. They’ve streamlined the company, moving their Don Mills store over to Yonge and Eglinton, while continuing to run the Collingwood and Mississauga stores with the service and expertise they’re known for.

Going up! The managing partners of Skiis & Biikes earning turns in Japan.

“In the ‘90s we were really well known, we had such a great brand and I think we kind of lost our North Star,” says Devin. “We really operate very well in the Southern Ontario area. So I think we’re just getting back to the basics. And now we’re in a better situation, we get to do the fun stuff. We get to do more events, we get to be out in the community, we get to do really ramp up our initiatives with giving people skiing; getting people excited about skiing.”

And getting people skiing is what the business has always been about.

“I think the kids can now really see what it takes to truly be successful,” reflects Paul. “I built them a foundation, I’m confident they can now build the house. One more person must be mentioned; Sharon, my wife, the kid’s mom has been the rock behind the scenes that keeps our perspective.” 

—ML

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