“I started Craig’s Cookies out of my tiny one-bedroom in Parkdale. A decade later, we have five locations across the city”

In Newfoundland, a lot revolves around the kitchen. I grew up in St. John’s, in a family that loved food and showed their love through food. Both my mother and my grandmother were avid cooks and bakers. When I was around eight, my mom brought me into the fold, teaching me how to make her chocolate chip cookies. I loved those cookies. My classmates felt the same way: in high school, I brought them to potlucks and watched people go back for seconds and thirds. 

After graduation, I studied saxophone at Memorial University and contemplated becoming a priest before finding my heart in acting. In 2004, I moved to Toronto, where I went to George Brown College to study theatre. I spent four seasons performing at the Shaw Festival in Niagara-on-the-Lake. My mom’s cookie recipe followed me to Ontario: I used to bring cookies to our Shaw openings and watch them disappear off the plates. Eventually, I found myself wanting to do newer works for a contemporary audience, so I moved back to Toronto to pursue a different kind of theatre. 

Related: How Craig Pike went from actor to king of a cookie empire

By 2013, I found myself back in the city, bartending to get by in between acting gigs. One day, late in April, the restaurant I worked at fired its whole staff, and suddenly I needed a way to pay my bills. I was going away in June to do a six-month acting role, so I didn’t want to take another job, but I also needed to buy groceries. From somewhere in my subconscious emerged a vision of chocolate chip cookies.

I had a small one-bedroom apartment in Parkdale and an oven that could only bake one dozen cookies every 10 minutes. I made a batch, took some photos and started posting them on Facebook and Instagram. At the time, no one was really doing food marketing on Instagram, and the cookies took off quickly. Before I knew it, I was baking around the clock. By the end of the month, I had sold 200 dozen cookies, at $8 a dozen, just through social media. I packaged them in brown paper bags with Craig’s Cookies written in marker and rode across the city on my bike, handing off batches.

Over the next few years, without fully realizing it, I built my brand one bike ride at a time. I started doing small markets, like the Parkdale Flea, in between filling more and more online orders. In 2017, I was invited to be on the cover of EnRoute magazine, which introduced my cookies to the Bay Street crowd. Williams Sonoma offered me a pop-up shop later that year. I got up at midnight and baked for nine hours. The cookies sold out in two. Then Williams Sonoma invited me to do a six-month pop-up in Eglinton Mall. That was when things started to get serious: in the first two months, the pop-up sold 40,000 cookies. I had to get a business number and a Costco membership.

At the same time, I was rehearsing a play and conducting a choir. Then I got an order for 10,000 cookies. Not knowing anything about how businesses work, I said yes. I was now baking at Williams Sonoma and in a small kitchen I had rented. In December 2017, I slept seven hours in five days. One day during that week, I was at Williams Sonoma and a customer was giving me a hard time. I just started crying. I thought to myself, This isn’t worth it. I’m exhausted, and I don’t even love cookies. My passion is the arts, and my passion is suffering because I’m so busy with this cookie business. I decided that I would stop Craig’s Cookies. It was a good run, five years, and that would be that.

Then, at the beginning of 2018, a friend tagged me in a post about a Parkdale storefront. I had always said to myself that, if there was ever a 200-square-foot space, I had to take it. That way, people would feel like they were coming into my kitchen: popping in for a cookie, telling me about their day and then going off again into the world. I took out a napkin and wrote down the numbers. If I could sell $80,000 worth of cookies a year, with myself and two other people working, I would be able to pay my rent and maybe go on a trip. I had never been somewhere tropical. I wanted a vacation. 

Related: “I had a successful corporate career, but food was my passion. Leaving it all behind to open a bakery was the best decision I ever made”

When we opened, in April of that year, BlogTO came by and did a video. It got 1.4 million views. Overnight, we went from selling $300 of cookies a day to over $1,000. Our staff went from two to nine. We finished that first year of operations at $570,000 in sales—and I did get to take a vacation.

Several months after we opened, I had an “aha” moment about what this business really was for me. It was Pride, June 2018, and I was looking at our yellow building. I realized that I had a responsibility as a small-business owner to have Craig’s Cookies reflect what I wanted to see in other businesses. As a member of the queer community, I wanted Craig’s Cookies to offer a safe and inclusive place for 2SLGBTQIA+ employees and customers.

So we painted the building rainbow. In addition to the fun decorations, we also started celebrating Pride every year with a signature cookie, in partnership with local queer organizations. This year, we have the Ruby Red: a white chocolate chip cookie dipped in pink chocolate with pink glitter. All proceeds from it go to Friends of Ruby, an organization that supports 2SLGBTQIA+ youth.

Creating that safe space also meant creating a good place to work. We pay our employees a living wage and offer benefits including mental health support. I match any kind of addition that our employees put into a group retirement savings plan. I also try hard to listen to our team and appreciate how they navigate the world. We do check-ins weekly, monthly and quarterly to try to ensure that staff members feel heard. At the end of the day, it doesn’t matter how many cookies you sell—people need to feel comfortable coming to work.

I’ve also had to learn how to navigate the emails we get concerning people’s, shall we say, distaste for rainbows. There’s still a lot of bigotry out there. I used to spend a lot of time replying to homophobic comments that trolls left on our pages. Five hours would go by, and I would just be so upset. Now, I do a segment on Instagram where I read out mean comments and make light of them. I try to focus on giving back to my community however I can.

In 2023, 10 years after I delivered my first batch, Craig’s Cookies now has five locations in Toronto, one in Newfoundland, and our first franchise opening in Niagara-on-the-Lake. I’ve also been able to re-invest into my passion for the arts. Last August, I launched That Arts Group, an umbrella organization that houses my choral work and a new theatre company. This fall, we’re producing Angels in America with Toronto-based queer theatre company Buddies in Bad Times. 

I’ve been very fortunate. Thanks to my mom’s recipe, the cookies basically sell themselves. But working with people, learning how to really see them and how to be brave enough to represent your values—those lessons take work. Growing up in Newfoundland, I never thought I would be living in Toronto and running a business. The big city is not where I expected to end up. The truth is, I had no dreams or ambitions to own a business at all. What I said to myself that day in Williams Sonoma is still true: I don’t love cookies. I love connecting with people. I love what cookies—and all food, really—can do for communities. They bring people together.