UpTrajectory Review
Jemma Chapman’s journey from job seeker to entrepreneur highlights the resilience and creativity often required of small business owners. After struggling to find work in architecture upon moving to Toronto, she turned her passion for illustration into a unique venture by selling her art through gum vending machines. This innovative approach not only showcases her artistic talent but also reflects a growing trend among entrepreneurs who leverage unconventional methods to reach customers.
For small business operators, Chapman’s story serves as a reminder that setbacks can lead to unexpected opportunities. Her ability to pivot from a traditional career path to a creative business model underscores the importance of adaptability in today’s market. As more individuals explore alternative revenue streams, consider how you might innovate within your own business. This week, think about what unique skills or passions you can transform into a product or service that stands out.
“I thought that before I invested in a job, I'd travel.” — Business Insider
Takeaway: Embrace setbacks as opportunities to innovate and explore new business ideas.
From the original item — Business Insider:
Courtesy of Jemma Chapman
- Jemma Chapman is a Toronto-based illustrator and the founder of Toonie Stamps.
- She moved to Toronto from the UK on a visa in 2025 and couldn’t find a job.
- She decided to sell tiny prints of her illustrations via gum vending machines.
This as-told-to essay is based on a conversation with Jemma Chapman. It has been edited for length and clarity.
I’m British, and I moved to Toronto in January 2025. I had qualified as an architect the previous summer and realized I had spent most of my adult life studying and not really living.
I thought that before I invested in a job, I’d travel. Traveling provides you with a great perspective as a designer.
I got a Young Person’s Visa between the UK and Canada, which allows me to live in Canada for two years. That’s when I came up with a unique idea.
I first had trouble finding a job
I came to Canada to find a job in architecture, but I struggled to find employment for eight months.
Only a handful of people responded to me. It affected me. I kept telling myself it was because I was a foreign talent.
It was hard because I had been building a life. My personal life was going great; I was meeting people and volunteering. I was enjoying Toronto, but the job was a key missing component for the longevity of living here.
In my free time, I had been drawing little illustrations of buildings and memories throughout the city. I’d frame them at home as stamps because stamps are a nod to a place and time, and I wanted to have icons of my time here.
Courtesy of Jemma Chapman
My friends told me I should share them on social media. I was worried about accumulating more debt and about people not being kind to me.
But on a particularly rubbish day last October, I thought I’d make one video about my art project. One hundred people followed me, and then another hundred more. Very quickly, they were asking where to buy them. It was crazy because I don’t see myself as an artist.
I began selling my tiny prints
I believe the only way people can appreciate and value art is by having access to it, engaging with it, and understanding the joy of owning it.
I began selling my tiny prints for $2 online under the name Toonie Stamps.
I wanted to provide people with a way to access them physically, too, because this project is a documentation of my experience in Toronto. I wanted to encourage people to explore the city. I bought a gum vending machine on Facebook Marketplace, not knowing if my art would even fit inside. I painted them and branded them, and a friend who worked in a barbecue restaurant told me he could put the gum vending machine there. I did that in January 2026.
Courtesy of Jemma Chapman
I now have 6 machines. Each of my machines has a neighborhood map. If people are going to that area of town, maps are a way I can encourage them to explore other local places in that neighborhood.
I’m coming from a country where independent retail is on its knees, so I wanted to celebrate that Toronto has a high percentage of independently and locally owned small businesses. Canadians are proud of where they live and very attached to it, so I think championing this helped me get a community behind it.
The art project became my business and changed my life
This art project has become how I earn a living, but it’s also linked to my ethics as a person, what I believe in, and what I’d like to use my art to champion.
I have six total machines now. One is installed in a historic post office downtown. That, plus the barbecue restaurant one, are my two permanent vending machines. I rotate the other four. Three are currently in subway stations because I recently launched a collaboration with the Toronto Transit Commission.
I now live off of three parts of my project combined: the machines and my online print sales, a mail club where I send pieces from the project to about 150 people a month, and commissioned work.
My visa expires in January 2027, but I can extend it for another year. I hope I get a sign-off on it.
I would encourage everyone to share their art with the world. It was scary at first; I still feel nervous when I share new designs, but it’s always a pleasant surprise at how well they’re received.
My advice: Emulate in the world what you want to see. Fill the gaps you think are missing; you might be surprised by how many others are happy to see those spaces taken up.