In May 2020, Matthew Kesselring and his friend Luke Macintosh started an online skateboard delivery service, Skatedrop.
They initially wanted to sell and deliver skateboard goods to their friends but then decided to expand it into a small business for the local skateboarding community. During the COVID-19 pandemic, the two friends came up with the idea of selling and delivering skateboards for the community in Kitchener-Waterloo. They partnered with Thrift Piff, a local vintage store, where they got a physical space for their business.
When Macintosh left Skatedrop in September 2020, Jerry Quartz joined as a co-founder and oversees media and website management for the business.
They decided to start their business in Kitchener-Waterloo since they grew up in the community.
“We felt like our business is a way to give back to our community,” Kesselring said. “There was really a big gap in the community. Like there were no local skate shops.”
To attract customers, skateboard shops need distribution deals with multiple skating brands. They initially formed a partnership with a skateboard brand, Dwindle. When they started their business, they found it difficult to find distributors interested in partnering with them.
“Skateboard brands have a weird set of rules that you need to follow to form partnerships with them,” Kesselring said.
Skatedrop gained much support from the local community once it opened to the public.
“The reaction was immediate. Instantly, people were buying our stuff, following us on Instagram, and supporting us,” Kesselring said.
They went on to partner with Apollo Cinema for the premiere of All the Streets Are Silent, a sports documentary released on July 23, 2021. They even screened an ad and sold merchandise such as trucker hats through their partnership.
The owner of Thrift Piff contacted the business earlier this year, asking if they would like a physical space for their business.
After getting a physical space for their business, Skatedrop expanded its distribution and partnerships with other skateboard brands, such as Comacan Skateboards.
Quartz described how the service operates around the local community of Kitchener-Waterloo and other regional communities surrounding it in a 30 km radius. He also said skateboarding has become a mainstream leisure activity and sport in the Kitchener-Waterloo area due to its four skate parks and people’s enthusiasm to learn how to skateboard. He is glad that skateboarding has become inclusive to 2SLGBTQIA+ and racial communities across Kitchener-Waterloo.
“It’s refreshing to kind of see more and more diversity within the community,” he said.
Skatedrop has shown interest in selling merchandise other than skateboards to promote the shop.
However, they say they want to focus more on skateboards since it’s the main product of the shop.
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