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Ashley Freeborn

Forty Under 40 winner 2019, Co-owner, Smash + Tess, Age 37
Chung Chow photo

Ashley Freeborn had long dreamed of becoming an entrepreneur but it was not until the summer of 2014 when she became determined to make that dream a reality.

She had enrolled in the Condé Nast College of Fashion & Design in London for a three-month course that summer and was inspired to return to Vancouver and put together the business plan for what would become Smash + Tess.

She is the Smash in that name, while her mother, co-founder Teresa Freeborn, is the Tess. The duo put plans in place and designed and produced their company’s line of rompers – comfortable one-piece fashions for women.

“I was very out of my comfort zone,” she told Business in Vancouver.

“If you’d asked me 10 years ago, I would have never thought I would have been an entrepreneur.”

Her father, she said, had drilled into her the importance of going to university and getting a secure job, and she took that advice to heart.

She completed bachelor of arts, bachelor of education and master of education degrees at Simon Fraser University.

That led to more than a decade of teaching in School District No. 43 in Coquitlam.

Indeed, she continued teaching when she co-founded Smash + Tess. She left that job to work from Vancouver for California-based Xceed Financial Credit Union, overseeing the credit union’s loan portfolio and then teaching staff.

“It wasn’t that Smash + Tess was a hobby,” she said. “I probably could have quit the corporate world a long time before I did, but I’m extremely conservative, and I needed to make sure that my cash flow would be good. I didn’t want to take the risk because being an entrepreneur was not something that was ingrained in me.”

Annual revenue now exceeds $10 million, and she is aiming to increase that to the $15 million range next year thanks in part to a partnership with Corus Entertainment to make rompers that incorporate images of Sesame Street characters.

She has been recognized as a finalist at the 2017 Mompreneur Awards, in the Startup category. She was also a finalist at the 2019 YWCA Women of Distinction Awards.

Birthplace: Richmond, B.C.

Where you live now: Vancouver and Los Angeles

Highest level of education: Master’s in education from Simon Fraser University

Currently reading: What Remains: A Memoir of Fate, Friendship and Love by Carole Radziwill

Currently listening to: Khalid or Van Morrison. Depends on my mood

When you were a kid, what you wanted to be when you grew up: A singer or a fashion designer. One of those things I am; the other I am as well – but maybe just alone in my car

Profession you would most like to try: Author. I wrote a children’s book last year. I have several book ideas. If only I could clone myself

Toughest business or professional decision: To leave my safe, corporate career a year and a half ago and put everything into Smash + Tess. Turns out it was the right decision

Advice you would give the younger you: To never be afraid to take the leap; all of the best learning happens when we are thrown off balance

What’s left to do: World domination – one romper at a time

Join us to celebrate the 2019 Forty under 40 Awards on January 30, 2020, at the Westin Bayshore. For tickets and event information visit