Orillia entrepreneurs describe how business coaching helped turn a skate shop dream into reality
The following article was provided by the Orillia Community Development Corporation.
You don’t have to know the difference between a kickflip and a boardslide to appreciate what makes Pocket Skate & Vintage successful.
Located at 121 Mississaga St. E. in the heart of downtown Orillia, the shop is known for its skateboards, snowboards, accessories, and carefully curated collection of vintage clothing. But ask almost anyone who’s walked through the door, and they’ll tell you it’s about much more than a retail space.
Co-owners Grace Schofield and Mark Watson have created a place where community comes first — from six-year-olds learning their first ollie to adults in their 50s and 60s returning to a sport they loved growing up. Whether you’re a complete beginner, a dedicated teenage skater, or a seasoned rider getting back on a board, there’s a place for everyone.
Long before the doors opened, even the shop’s name was born from that same sense of community during a backyard conversation with friends.
“Pocket” immediately stood out. It was the name of a much-loved cat, but it’s also a skateboarding term referring to the ideal placement of your back foot when setting up for tricks like an ollie or kickflip. The name perfectly captured both the close-knit friendships behind the business and the skate culture at its heart.
Throughout the year, Pocket hosts skate jams, live music, community events, and fundraisers to help build a new skatepark in Orillia.
Schofield’s and Watson’s goal has never been simply to sell products — it’s to create a space where people can connect, express themselves, and feel like they belong.
Two paths, one shared vision
Although Schofield was only 21 when Pocket opened, entrepreneurship had been on her mind for years. She imagined owning a café or retail space — a place where people could gather, build relationships, and feel at home.
“As a teenager, I always worked for small, local business owners, never big-box stores,” Schofield says. “I think that entrepreneurial spirit just rubbed off on me.”
Creating and selling tie-dye and vintage-inspired clothing on the side gave her an early taste of entrepreneurship and confirmed what she already knew — she wanted to build something of her own.
“My extended family never looked at owning a business as an impossible dream,” she says. “It was always, ‘We’ll figure it out.’ Having that kind of support made it easier to believe I could create something myself.”
For Watson, the dream started when he bought his first board at age 11 and quickly fell in love with both skateboarding and snowboarding. From that point on, owning a skate shop wasn’t just an idea — it became a lifelong goal.
Over the next 20+ years, Watson built an impressive career in the skateboarding and snowboarding industry, developing expertise in retail management, sales, equipment, brands, and customer service.
“The knowledge was there,” Watson says. “The challenge was figuring out how to turn that dream into a business.”
Recognizing that entrepreneurship is easier with complementary strengths, Watson partnered with Schofield. Together, they combined his industry experience with her entrepreneurial mindset and passion for building community.
Entrepreneurship during uncertain times
Schofield and Watson had passion, experience, and a clear vision. What they didn’t have was experience running a business — or easy access to financing.
“When we opened in 2020, it was right in the middle of the pandemic,” Schofield recalls. “Banks were hesitant to lend to start-up businesses because of all the uncertainty.” Fortunately, Schofield already knew where to turn.
Years earlier, she had been hired through a Youth Employment Program offered through the Orillia Area Community Development Corporation (CDC), giving her firsthand experience with the organization.
The power of having the right support
When Schofield and Watson decided to open Pocket Skate & Vintage, they had the vision but didn’t have the capital to bring their dream to life. The budding business partners understood the CDC’s commitment to helping local entrepreneurs succeed.
Located on Peter Street South, the CDC is the region’s business centre, providing entrepreneurs with business coaching, educational workshops, and flexible financing to help them start, grow, and expand businesses.
The CDC helped Schofield and Watson build a strong business foundation. “The program gave us the building blocks we needed,” says Schofield. “It covered everything from determining whether our business was sustainable to marketing, payroll, financial projections, and writing a business plan.”
The co-owners received workbooks and planning templates, and they met twice a week with a business advisor who guided them through every stage of the planning process.
“You have to put the work into it,” Schofield says. “Our advisor challenged us, answered our questions, and helped us think through every decision. It was basically business ownership 101.”
With a solid business plan in place, Schofield and Watson applied and were approved for a loan that made Pocket possible. The financing allowed them to purchase their initial inventory, install fixtures and display racks, and transform an empty storefront into the welcoming space customers know today.
Equally important, the loan was structured with flexible repayment terms that gave the new business time to establish itself before full repayments began — something traditional financing often can’t offer.
“That flexibility made a huge difference,” Schofield says. “It allowed us to focus on building our customer base instead of worrying about immediate loan payments.”
Today, the loan has been fully repaid, but Schofield says the impact of the CDC extends far beyond the financing.
“They didn’t just give us a loan,” she says. “They gave us the confidence, knowledge, and support we needed when traditional financing wasn’t an option. Without the CDC, opening Pocket Skate & Vintage during the pandemic would have been much more difficult, if not impossible.”
Looking back, Schofield considers the CDC an essential part of their success. “They were instrumental in our journey,” she states. “They genuinely care about local businesses and want to see entrepreneurs succeed. Having that support gave us the confidence to take the leap.”
More than a store
Today, Pocket employs five people, including Schofield and Watson. Their staff aren’t simply retail employees — they’re passionate members of the skateboarding community who enjoy sharing their knowledge and helping newcomers feel comfortable.
That sense of community doesn’t stop at the shop’s front door. It extends to the broader business community, where Grace and Mark believe collaboration is far more valuable than competition.
“Community is always more important than competition,” Schofield explains. “There’s enough business for everyone. When local businesses support each other, Orillia and the surrounding community benefit.”
Looking ahead
As the business continues to grow, Schofield and Watson are already thinking about the future.
They hope to move into a larger location with additional retail space and a dedicated area for their in-house printing operation, while creating a better environment for customer meetings and collaboration with local artists.
Pocket Skate & Vintage has become far more than a retail store. Inclusivity, community, and connection are core enduring values that have transformed this Orillia business into a destination where people come not just to shop — but to belong.
The right time to start a business
Schofield often hears from people who dream of starting their own business but wonder if they should wait for the “right” time.
Her advice is simple. “There is no perfect time,” Schofield says. “If you wait until everything feels certain, you’ll probably never start. It’s scary, but sometimes you just have to leap.”
But taking that leap doesn’t mean doing it alone.
For Schofield, the biggest lesson is that entrepreneurship is not about having everything figured out before you begin — it’s about being willing to learn, ask for help, and take that first step with the right support behind you.
“The CDC was instrumental for us,” she says. From developing a business plan and understanding financial projections to accessing financing and having an advisor to answer questions, the CDC provided the foundation Grace and Mark needed to turn an idea into a successful business. “They helped us understand what it takes to run a business and supported us every step of the way.”
Thinking about starting a business?
The Orillia Area Community Development Corporation helps entrepreneurs plan, start, grow, buy, and sell businesses through coaching, educational workshops, and flexible financing.
To book a consultation or for more information on the Orillia and Area Community Development Corporation, click here or call 705-325-4903.