John James (JJ) Wilson, 30, is a retail entrepreneur who has worked with brands such as Lululemon, Holt Renfrew and wings+horns. He co-founded clothing company Kit and Ace, which was sold in 2018, and today co-owns Ride Cycle Club, a chain of indoor spin studios in Vancouver and Toronto. He recently launched a Ride clothing brand and is a partner at Very Polite Agency. Mr. Wilson has a Bachelor of Commerce degree in entrepreneurship and retail management from Ryerson University and recently graduated from Harvard’s owner/president management program.
I was born and raised in Vancouver to an ultra-conservative Catholic mother, Nancy Herb, who I love dearly, and a free-spirited, entrepreneurial hippie father, [Lululemon founder] Chip Wilson, who I also love dearly. I have one full brother and my father got remarried and had three more sons with his wife, Shannon.
My passion for starting businesses and enrolling people to help build them started when I was a kid. I started a little clubhouse in my neighbourhood – inspired by one of my favourite movies back then, The Little Rascals – and we did things to raise money like sell lemonade and wash cars. Chip, being the entrepreneur he is, always tried to coach us through things like operating costs and gross margins. My playtime, until I was in my teens, was the clubhouse and our passion was finding ways to make money.
Chip wasn’t a traditional father. He would pull us out of school to go to a trade show, to visit a manufacturer overseas or to go and join the [initial public offering] tour. I also started working at the Lululemon stores. I loved every minute of it. Chip did an amazing job of integrating us into the business while also being a parent.
I worked as a trend forecaster in Toronto at Holt Renfrew, while finishing my degree at Ryerson. I then moved to New York City and later Boston, before coming back home to Vancouver, where I started working at wings+horns. I then left to work full-time at Lululemon, with a focus on its growing men’s line.
Our family wasn’t aligned with the Lululemon board. Ultimately, the board asked the Wilson family to leave the business. Effectively, I got fired from the company my family started. It was an interesting feeling and experience. I went through the grieving stages: I was angry, then sad, then I forgave.
When Chip, Shannon and I co-founded Kit and Ace in 2014, it was successful immediately and grew at a rapid pace. The challenges we had weren’t necessarily out of our control. The biggest problem was that the business had too much access to capital. It didn’t put pressure on the business to be creative in how it ran itself. This is my biggest learning. Also, Shannon, Chip and I all had a slightly different vision and approach. I don’t look at Kit and Ace as something that didn’t work out. It’s still around and doing a really good job.
I started Ride Cycle Club with my business partner Ashley Ander in the same year we started Kit and Ace. I first fell in love with spinning when I lived in Toronto. When I came back to Vancouver, I couldn’t find what I wanted. I wanted to start my own place, but I needed a business partner since I was also working at Kit and Ace.
Based on my experience at Kit and Ace, I’m very cautious about how much debt Ride Cycle Club takes on to grow the business. People are telling me ‘you can grow faster, you can be so much bigger.’ I’m not saying I don’t want to be, but for me, slow and steady wins the race. Selfishly, we are having so much fun with the business. I am enjoying myself and don’t want to compromise that.
The best advice I’ve had in business is to be egoless about what you don’t know and hire people around you that know things better than you. I get a lot of enjoyment around creating an idea and bringing people together to help create and execute that idea.
I’ve been doing a lot of work lately on developing a purpose statement for myself. What I discovered is that my purpose isn’t necessarily to go and be an entrepreneur. What brings me joy and puts me ‘in flow’ is having an idea and putting people together and then seeing those minds come together to bring that idea to fruition.
This interview has been edited and condensed.
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