Meet Ashley Freeborn, Founder of Smash +Tess and 2020 RBC Canadian Women Entrepreneur Awards Start-Up Finalist

Ashley Freeborn is the founder, principal and managing director of Canadian fashion brand, Smash + Tess. She was an educator for the better part of a decade, then made the leap to corporate training and culture where she worked in the finance sector for almost three years. Although she loved it dearly, Ashley still felt the need for a fun and fresh creative outlet – enter Smash + Tess. After finding a void in the loungewear market, she attended the summer fashion program at Conde Nast in London, UK, and the rest is history!

My first job ever was… I was 16 and was a hostess at one of the hottest restaurants in Vancouver. 

I decided to be an entrepreneur because… there was a hole in the market that I wanted to fill. That is what led me to starting Smash + Tess. It was the dream of creating the brand and the clothing that kicked off my business venture. I never thought that I would be an entrepreneur, but now I cannot imagine being anything else.

My proudest accomplishment is… my two daughters. They inspire me every day to grow my business and to create a legacy of women uplifting women.

My biggest setback was… my health. I struggle with Crohn’s Disease and sometimes it knocks me down pretty hard. But I’ve always managed to work through it. Of course I have moments of weakness or helplessness — but I don’t rest in those moments for too long or it starts to wear me down. Mindset is key, and I try to keep a perspective of gratitude.

I overcame it by… advocating for myself. Even at my sickest, I truly believe that where there is a will, there is a way. I’ve struggled through different medicines, alternative remedies, lifestyle changes – and just like in business, I’m tenacious and won’t stop until I find a solution that works for me. 

If you Googled me, you still wouldn’t know…  that I love music from the 60s and 70s – my parents passed along their vinyl collection, and nothing puts me in a better mood than listening to Bob Dylan, Van Morrison, or Janice Joplin.

My best advice for aspiring entrepreneurs is… to relish the moments where we feel off balance. It’s ok to feel frightened, because it’s in those moments of uncertainty that we do the most growing.

The one piece of advice I give that I have trouble following myself is…  to let go. I am a natural problem solver and sometimes I have to learn how to let go of the things I cannot control. 

Success to me means… creating the kind of life you love living. There really is no such thing as a weekend for me. I love Monday mornings just as much as I love Sunday mornings. It’s a beautiful thing.

I stay inspired by… listening to our community. The dialogue that I’m lucky enough to have with our #smashtessfam continues to inspire me to be innovative and to disrupt the fashion industry with clothing made for every day, for every occasion, for every woman. 

My next step is… world domination… one Romper at a time!