A few months ago, Sam Armeland walked into Craig’s Cookies on Bloor Street, asked to leave a note for the owner, and went home. The note said he had started a cookie business and wanted to collaborate. He was 9 at the time.
Craig Pike saw the note. Shortly after, Sam’s dad Adam ran into Pike at an industry conference, and Pike mentioned he had been planning to reach out. After a few months of back and forth, they landed on World Book Day, April 23rd, as the right occasion. Sam would take over the counter at Craig’s Church Street location at 483 Church St., manage store operations while Pike stepped back, and direct 100% of proceeds from his cookie pick to the Toronto Public Library Foundation.
On the day of the event, Sam’s Pick sold out.
“The first point of contact was actually Sam walking into Craig’s Bloor Street location and dropping off a note saying he had started a cookie business and wanted to collab,” said Adam Armeland, President of Toronto-based Kitchen Hub. “And then I ran into Craig at a conference, and he mentioned he had seen the note and was going to reach out. After a couple of months of going back and forth, we landed on a nice reason to collab, which was to raise money for the Toronto Public Library.”
What made the event unusual was the direction of the mentorship. Craig Pike, who has built one of Toronto’s most recognized food brands over 13 years, was not there to teach Sam how to run a cookie business. He was there to learn from him. The two held a Milk and Mentorship session where Sam offered business advice to Pike in front of customers. A 9-year-old, behind the counter, telling a founder with 24 locations what he thought about the business.
“Entrepreneurship is learned through practice, through trial and error, failing, starting small, and trying again,” Adam said. “The earlier you start developing these skills, the better equipped you are to build something meaningful later in life. What makes this collaboration special is watching an established entrepreneur like Craig recognize that mentorship works both ways. Sam’s approach to business, his creativity, his hustle, his willingness to just start, has lessons for all of us.”
For Pike, the moment Sam walked through the door on World Book Day carried real weight. “When I saw that note Sam had left for me, I knew this kid had something real,” Pike said. “Any young person willing to walk into a store, introduce themselves, and put their idea in writing deserves to be taken seriously.”
Pike built Craig’s Cookies starting in 2013 by delivering cookies on his bike to cover his rent. He posted on Facebook and Instagram, sold 200 dozen cookies in his first month, and spent five years building entirely through delivery and word of mouth before opening his first retail location in 2018. COVID, unexpectedly, accelerated things.
“Everybody wanted cookies,” Pike said. “It really helped build the brand in ways we did not expect.”
The brand now operates 24 locations across Canada, with a franchise in Halifax that opened roughly three months ago and a location in St. John’s. The Union Station opening was a personal milestone. “I remember standing outside on opening day thinking, what is life. This is wild,” Pike said. “I’m from Newfoundland. I moved to Toronto 20 years ago. To be able to have our presence at Union Station and share our cookies with even more of the city, that was something else.”
The city has since claimed the brand entirely. “They just call it Craig’s now. Not Craig’s Cookies. Just Craig’s. That still blows my mind.”
Hosting Sam at the Church Street location, one of Craig’s earliest stores, was deliberate. “Having Sam here at Church Street, one of our first locations, being able to give him a full tour, it all comes full circle,” Pike said.
Behind the counter that day, the two talked cookies the way people who actually bake talk cookies. Craig’s favourite of the day was the cinnamon bun cookie Sam had brought from home. “It is so cinnamony and the dough is so good,” Pike said. “That is my favourite cookie right now. Your cookie.”
Sam had done his research on the Craig’s menu before arriving. “I found one that I thought would be really crazy to actually get,” Sam said. “A Root Beer Float Cookie.”
They debated a lemon cake bun Sam has been working on. “It is hard to make the texture of the lemon cake for the bottom,” Sam said. “I haven’t tried it yet but I know it is going to be hard.”
Pike’s response was grounded in experience. “We tried to make a lemon meringue pie cookie and that was really difficult. We just keep testing. Sometimes it takes weeks to get it right.”
When Craig asked what the wildest thing Sam would ever put in a cookie was, Sam said pizza. Pike leaned in. “I have tried that before. Can I tell you the secret? It is really good.”
Sam’s Pick, the Mars Bar cookie, sold out. His process for choosing it was straightforward. “I just looked at the website and picked the one I thought I would like the most,” he said.
When 6ix Retail first covered Sam Cooks last October, Sam had sold roughly 750 cookies in three weeks through samcooks.ca, a site he built overnight using Webflow and AI prompts. On his busiest days he wakes at 6:30 a.m. to bake up to 240 cookies before school. Seven months later, total sales sit at approximately 4,000 cookies. His menu has grown from a single chocolate chip to Oreo, red velvet, birthday cake, and Biscoff. A Mini Eggs flavour came and went.
“No one really ended up ordering it that much so we decided not to make it anymore,” Sam said. “But every once in a while we would get a note saying can you please bring it back.” The person sending those notes, it turned out, was his grandmother. She now gets a custom batch when she asks.
Mother’s Day was the biggest single run yet. Sam introduced a pink velvet and a birthday cake cookie with pink sprinkles. “It was on fire,” he said. “We did 300 cookies in two days.”
The operation has grown structurally too. “What has been really cool to watch is Sam learning to delegate and build a small team around him,” Adam said. “Every Wednesday night he and his mom Jess go over inventory and upcoming orders. He assigns tasks to whoever is helping, and when he needs extra hands he brings in a friend and pays them for their time. He is running an actual operation.”
The Craig’s Cookies event generated two new partnership inquiries that Sam and Adam are not yet ready to name publicly. Sam has also been invited to speak at his school about starting a business, and his school librarian has asked him to speak to his sister’s class specifically about the Toronto Public Library collaboration.
For Pike, the collaboration reinforced something he has been building toward since 2013. “Our goal from the beginning has been to make delicious cookies and make people happy, but also to engage with the community in a meaningful way,” he said. “Working with Sam reinforced that for us. It is not about chasing big co-branded deals. It is about looking around your community and asking how you can show up for the people in it.”
After the event, Sam’s friends and family had one consistent reaction. “They mostly said that was so fun and they want me to do another collaboration with someone,” Sam said.
He will. He is heading into summer with two partnership conversations underway, a sold-out collaboration on the books, and a s’mores flavour in development. He is also going to the same Nova Scotia camp his dad attended as a kid, where cookies are delivered to cabin doors every night. He is already thinking about whether he can arrange to bake for the whole camp one evening.
“Then all my friends might want to order it when we get back,” he said.
Dustin Fuhs is the founder and Editor-in-Chief of 6ix Retail, Toronto’s premier source for retail and hospitality industry news. As the former Editor-in-Chief of Retail Insider, Canada’s most-read retail trade publication, Dustin brings over two decades of expertise spanning retail, marketing, entertainment and hospitality sectors. His experience includes roles with industry giants such as The Walt Disney Company, The Hockey Hall of Fame, The Canadian Opera Company, Starbucks Canada and Blockbuster.
Recognized as a RETHINK Retail Top Retail Expert in 2024, 2025 and 2026, Dustin delivers insider perspectives on Toronto’s evolving retail landscape, from emerging brands to established players reshaping the city’s commercial districts.