Inniskillin Changemaker: Ashley Freeborn


“Instead of getting beaten down, let’s remember that we started our businesses to accomplish something great. Let that guide you.”

In partnership with Inniskillin, Canada’s first estate winery, Startup Canada is celebrating and spotlighting leading entrepreneurial changemakers and disruptors across Canada. Startup Canada was pleased to sit down with Ashley Freeborn, CEO of Smash + Tess to learn about their journey and the impact of their work.  

Born and raised in Vancouver, BC, Ashley graduated from Simon Fraser University with a BA in English, a BEd, and an MEd. She taught school for a decade before co-founding Smash + Tess with her mother in 2016. The idea for Smash + Tess rose out of Ashley’s recognition of an unfilled niche in fashion —a void in the loungewear market. Deciding to fill that void with affordable, stylish, comfortable loungewear, she attended the summer fashion program at Conde Nast in London, UK. Bootstrapping her idea to life, S+T has grown from two employees into a team of 23 in just four years. In 2019, the business achieved 100% YOY growth, surpassing $10 million in sales.

Ashley recently published her first children’s book, Frankie and the Magical Romper, now on sale at Chapters Indigo. Business in Vancouver named her to their 2019 Top Forty Under 40, and the CANIE BC Region chose her as their 2020 Entrepreneur of the Year. Ashley is also one of the top three finalists in the startup category for the RBC Canadian Women Entrepreneur Awards and was also named by the Globe and Mail as the  #1 female founded growth company in 2020. Most recently, she was named as one of Canada’s Top 40 under 40.

SC: In one sentence, what does being an entrepreneurial changemaker mean to you?

AF: Being an entrepreneurial changemaker is about taking creative action to fill a void in the market, challenging the status quo with disrupting and exciting ideas, and following that up with practical application.

SC: Tell us about your entrepreneurial venture(s) – what do you do? What role has it played in your life?

AF: We are pioneering the romper revolution at Smash + Tess. We exist to make the lives of our women customers – and now men and children customers – easier. We do this by offering clothing that is locally made by skilled artisans that are made to last. But most importantly, we are simplifying our women’s line by having “the outfit to go from the streets to the sheets” in. Life is hard enough and you shouldn’t have to stress about what to wear every morning. We exist to uplift and support women but more importantly we really are a community, a lifestyle, and a shared digital and creative space.

In terms of work-life balance… what balance? For me, work and life truly are the same. I am SO excited about Mondays – I love Monday mornings – it’s my favorite time of the week. I find so much fulfillment out of what I do that it doesn’t feel like work. I do understand that at times it can be consuming while running a business but I also get that there are times when we need to unplug and just connect with our family. I have two little girls and they keep me grounded – they really snap you out of the work side of things – usually with lots of laughs and lots of cuddles. Really, I think it’s about finding and making time for the things that make you happy. Just carve out the time.

SC: What motivated you to become an entrepreneur?

AF: I never thought I would be an entrepreneur. I started off as a teacher for 10 years then moved onto the corporate world for a bit. What motivated me was that I saw a hole in the market and a void that needed to be filled. I have a very creative and tenacious side so I knew I wanted to fill that void. That’s what drove me and still drives me. I never set out to have this lifestyle and sometimes it is very scary being an entrepreneur, especially in 2020. But at the end of the day, that hole in the market I noticed four and a half years ago still keeps me going.

SC: What are you most proud of related to your venture(s)?

AF: I would say the community. I am so proud of this shared digital space that we have created that really does uplift women and cheer for women. For me, I have been so fulfilled and so deeply honoured to be a part of this community that literally fills my soul every single day. I could say I am most proud of the clothes – and I am, I absolutely love our products – or our Instagram growth, but honestly I am most proud of the community.

SC: Tell us about your biggest hurdle – what was it and how did you persevere  through it?

AF: I think anyone in apparel would say that production is a really big challenge. I think starting a new brand and not having any connections or not knowing how to bring your ideas to life is the top question I get from other entrepreneurs. It’s really about putting your feelers out there, putting one foot in front of the other and asking everyone you come across the right questions. The biggest thing, though, is your tenacity. You have to have that tenacity. For us, it was so hard to find production houses that wanted to work with us as we didn’t have a lot of volume to offer and we didn’t even really know where to start. We definitely made mistakes in the beginning but I think we just persevered – we pushed through. I always say that it’s not that I am any smarter or work harder than anyone else, I just have my sights set and push through even when there are one million obstacles in my way.

SC: What has your biggest learning been along the way?

AF: I always say my biggest takeaway has been trying to sit in the discomfort and fear of risk taking and knowing that it is okay to feel off balance because that’s actually when we are learning. It is in those moments when we feel completely thrown off balance that we often experience the most growth, we learn the most about ourselves, about what it takes, and about what we are made out of. For me, when things are too calm and too easy I start to get a little bit antsy and that’s when I realize it is time to start growing again.

SC: What drives your motivation when things get tough?

AH: Our customers. I believe in what we offer, our products, and our community. It can sometimes be easy to get wrapped up in the negativity when things aren’t going the right way, but at the end of the day I think about all of the smiles that we bring to our customers and how much these people deserve to feel and look amazing. That pushes me forward.

SC: Where can people go to learn more about your journey and organization?

AH: Social media is big for us – our Instagram handle is @smashtess. On our website we have a blog that myself, my co-founders, and our customers regularly contribute to. Under the about us section, people can learn where our clothing is made as well.

SC: What is your ideal vision for Canada’s entrepreneurship community over the next 20 years?

AF: Ultimately it is time for Canada to grow our impact globally. I think there are a lot of powerhouse brands that come out of Canada and it is a uniquely collaborative country that has led to a uniquely collaborative entrepreneurial community. If we keep working together, I think Canada can continue to make a great impact globally.

SC: What do you think today’s entrepreneurs should be focused on for a better, brighter future?

AF: We need to be focused on our ethos. As entrepreneurs we need to remember what our values are – especially right now with things being so challenging for a lot of entrepreneurs. I believe if we stay true to what we set out to do and what our mission was without sacrificing those values, it is clear we will have that brighter future. Additionally, I think it is important for entrepreneurs to have full confidence in what they offer. Instead of getting beaten down, let’s remember that we started our businesses to accomplish something great. Let that guide you.

Are you an avid supporter of Canada’s entrepreneurship community? Share Ashley’s story or showcase your OWN entrepreneurial changemaker across social platforms with the hashtag #CheersToTheChangeMakers!