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Meet Ashley Freeborn: founder of Canadian fashion brand Smash + Tess

Founder and Managing Director of Smash + Tess,  Ashley Freeborn spent the better part of a decade working as an educator before making the leap to corporate training and culture, where she worked in the finance sector for almost three years. Although she loved it dearly, she 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 a hostess at a hotspot in Kits, Vancouver BC. I was 16 years old and loved the freedom associated with earning my own cash!

The biggest lesson I have learned from my two big career transitions is… That you are never stuck! I’ve learned to open my mind and say ‘yes’ to opportunities. Good things come to those who are open and aren’t afraid to take a calculated risk!

I decided to be an entrepreneur because… I didn’t choose the entrepreneur life, the entrepreneur life chose me! When I started Smash + Tess I knew that it was something special, but I always intended to keep my corporate job. I was more comfortable with the idea of having job security. But now, I can’t imagine not being an entrepreneur. I LOVE that I can affect change quickly and that I’ve found an avenue for my creative side.

My proudest accomplishment is… Creating a brand and community where women uplift other women – where women of all shapes and sizes are celebrated equally. Smash + Tess is all about girl power and I have always considered us as more of a lifestyle brand, encouraging positivity, comfortability, and fun!

My boldest move to date was… Leaving my 9-5. If I’m being honest, I still wait for the sky to fall. I’m so conservative by nature, and continue to engage in a lot of self-talk and self-love, assuring myself that Smash + Tess is not just going to fail overnight. As an entrepreneur, your highs are so high, and your lows are so low. So I’m learning how to find balance and security in this new kind of life that I’ve created for myself.

I surprise people when I tell them… That I was a teacher for 10 years and have a Masters’s degree in Education. But really so many of those skills are now parlayed into my current career. Being an educator is really about building a community- and that’s my main focus of Smash + Tess… also, it definitely helps with all of the public speaking engagements!

My favourite product in my collection is…Definitely the Sunday Romper. It was the first Romper we ever did and it really started the Romper Revolution. It looks amazing on all body types, never loses its shape, and continues to be our bestseller. Many brands have done jumpsuits in the past, but Smash + Tess truly pioneered our signature silhouette, feel, and branding.


At the end of the day, you have to trust your gut — it will tell you what the right path to take is… you just have to listen.


My best advice to people thinking about leaving a 9 to 5  to start a business is… Do what feels right for you. There is no one way to take this leap. If you feel more comfortable transitioning slowly then do it your way. If you want to do a swan dive into the unknown — then go to it! At the end of the day, you have to trust your gut — it will tell you what the right path to take is… you just have to listen.  

A piece of advice that I often give but find it difficult to follow is… To relish the moments where you feel off balance. It’s in this discomfort that all of the learning happens. 

I would tell my 21-year old self… To GET IT GIRL! I was so unsure of who I was when I was 21. I could have been an entrepreneur then, but I was so scared. I’ve always been petrified of failure- but what I’ve since realized is that these failures mean growth, and growth is so important to me and my goal to be the most self-actualized human I can be!

My biggest setback was… My own self-doubt. Continuously worrying myself sick that I won’t succeed and that I’ll let myself, my family, my partners, and my team down.

I overcame it by… Putting one foot in the front of the other… I just keep plugging away and staying focused on my goal. I always say, the harder I work, the luckier I get.

The best thing about being an entrepreneur is… The creative freedom. I LOVE that I get to have an idea and very quickly, that idea becomes a reality. It is so exciting and having an ability to express my creative side is almost as important to me as the air I breathe.

If I had an extra hour in the day, I would… Hang out even more with my 2-year-old daughter. She has taught me so much about the world, about love, and about myself.

If you googled me, you still wouldn’t know… That I LOVE to ride motorcycles!

The future excites me because…I have SO many ideas that it’s hard sometimes to keep them straight! I’ve learned about the incredible things that can happen when you act on your dreams… and I have a lot of dreams… so look out!

My next step is… World domination- one Romper at a time! Bringing joy to the lives of our #smashtessgirls continues to drive me every day!