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From educator to founder, Ashley Freeborn of Smash + Tess shares why building community should be at the top of every entrepreneur’s checklist.

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Fashion trends may come and go, but you know what will never go out of style? Comfort, convenience, and community. At the helm of a movement that celebrates all three is Ashley Freeborn, Founder and CEO of Smash + Tess.

Originally a teacher, who then ventured into corporate culture and training in the finance sector, Freeborn found her true calling as an entrepreneur when she noticed a gap—and a problem—in the fashion industry. Not only was fashion a huge contributor to issues like global warming and the destruction of women’s self-esteem, shopping for clothes (at the time), was primarily a time-consuming, in-person activity. She knew there had to be a better way.

So, she packed her bags and set off for the Condé Nast College of Fashion & Design. She took what she learned, came back to Canada, and launched Smash + Tess. 

Known for creating the “Romper Revolution,” Freeborn was an early adopter of e-commerce technology, size-inclusivity, and using social media to build community. The result? A dedicated online fanbase of over 290,000 Instagram followers and a booming business.

“It’s really built by the input of the community, what they want to see, what styles, what colors,” said Freeborn. “I think the product is key for sure, don’t get me wrong. But I think what’s sustaining and building the momentum in this movement, which we call ‘The Romper Revolution,’ is the community.”

Freeborn says it took a while for the fashion community to accept and recognize Smash + Tess’s one-piece wonders, aka rompers, as fashion, and credits the brand’s community for really putting it on the map. Now, rompers are a must-have in the closet of everyone who values comfort while staying fashionable.

Over the years, Smash + Tess has been able to count many notable names as fans, including Kate Hudson, Gabrielle Union, and Hilary Duff (who recently released a collaboration with the brand). But for Freeborn, the best part of her job is seeing how Smash + Tess gets to be a part of the joy in people’s everyday lives around the world.

“It’s like a “pinch me” moment. I never take it for granted. I feel so much gratitude when I see someone’s wearing it [Smash + Tess] on their child’s birthday and they’re matching [with their kid] on such a special day and I get to be there, through our clothing,” she said.

For this week’s Entrepreneur of the Week, Bay Street Bull spoke with Ashley Freeborn, Founder and CEO of Smash + Tess about the importance of cultivating community, building a socially responsible brand, and leading the “Romper Revolution.”

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You have this whirlwind of a career, from being an educator to going into the corporate world, in the finance sector, to taking a leap of faith and entering a summer fashion program in the UK. What was running through your mind when you decided to make that career change?

I didn’t always think I was going to be an entrepreneur. I went into teaching, and obviously, I wanted to build community, but I also really enjoyed the security of it. So, I never started Smash + Tess thinking that I was all of a sudden going to take this entrepreneurial leap. 

What I felt was a hole missing, not only in the clothing and loungewear industry but also in the way that we shopped. At the time, 2014, I went to Conde Nast College and brick and mortar was the thing. People were online shopping, but not in the same way. And so the vision I had was to create comfortable, beautiful clothing that was going to simplify the lives of busy women everywhere, where they could shop at the touch of a click of a button. 

If you think about how busy we are as women these days, it’s insane how much we juggle. So, to create something that not only makes our lives easy because every day to get to wake up and be like, ‘I know what I’m wearing,’ and then to be able to shop online at our own convenience when it suits us in our schedule was something I wanted to do from the beginning. When we launched Smash + Tess, people were like, ‘So what stores are you going to be in?’ We told them we were going to be online—and people thought that was kind of crazy! Now, we hope we have a wholesale business as well, but we always wanted to disrupt the fashion calendar and the fashion industry, and do things a little differently from the beginning.

So, the entrepreneurial life found me. I was just trying to fill what I thought was a hole in the market. I thought, ‘Oh, I’ll just teach.’ And then even when I went into my corporate position, I thought, ‘I’ll just keep doing both.’ Then Smash + Tess began to gain momentum and snowball. When I became a new mother, I was like, ‘Oh, I can’t actually have a career all day, have a baby, and run Smash + Tess.’ It was one of those moments where I felt severe limitation and I had never felt that before. So, it kind of forced me to make a decision and say, ‘You know what? I think it’s time to go all-in on Smash + Tess.’ But it took me two years to get comfortable to do that. 

With that career change, from teaching and the corporate world, which were more traditional, safer career options, what was it like making the shift to entrepreneurship? Were there any kind of naysayers or people doubting the change, and if so, how did you overcome those voices? 

A lot of people. My own family was like, ‘Are you sure?!’ We came from a bit of a traditional background, where you went to school, you got out, you worked, you had a career, you had a pension, you had benefits. I still think my dad’s a little worried to this day [laughs]. Every time I talk to him, it’s ‘How’s business?’ And I’m always like, ‘Don’t worry, dad. I have my teaching license. I can always teach again.’ So, lots of naysayers. Also, just in terms of who we are as a brand. 

When you think of fashion, you think of thin models, you think of an unattainable lifestyle. When we came on the scene, people had been focused on selling their clothes in stores. People have been focused on more of an elevated fashion. And so when Smash + Tess came along, people kind of were like, ‘I don’t really get it. You’re selling online and you’re making rompers—is that fashion?’ We were banging on doors, wanting people to recognize us as a fashion brand. And I think what’s cool about it is we showed women of all shapes and sizes and colors and we shared user-generated content without curating it, we just shared it. And this was sort of revolutionary [at the time]. So our community seeing themselves in the brand and helping us build this community is what helped us show those naysayers that what we were onto was something pretty great.

It was the idea that fashion could be something enjoyable. Fashion could be something for everybody. Something that made you feel good, if you went up five pounds or went down, it didn’t matter. I think that the momentum of our community is what actually [helped us] land our first spot and Vogue and all of these publications in the beginning. 

And COVID-19 has flipped that on its head too. We’re both wearing sweatshirts right now! And so, it’s shaken things up. It’s hard to say that people are going to want to go back to wearing hard pants, because why would you? I can be really smart and I can deliver and I can work well and I don’t have to wear high heels to do it, you know? Comfort can be fashion and you don’t have to sacrifice one for the other.

I think you hit the nail on the head. There’s just such a disruption in how women’s fashion is portrayed in what’s accepted nowadays because of COVID-19. And Smash + Tess was a trailblazer in taking to social media and building an online community, especially within the leisure fashion industry.

Early adopters of Smash + Tess were already onto that. They were like, ‘Wait, I can just wear a romper!’ Then the pandemic hit and everyone wanted rompers. So, more people came [to Smash + Tess], but I think what makes them stay is this self-love, uplifting community that we have of women that have each other’s backs that are each other’s biggest fans

We’re so used to looking at these fashion brands and this hard editorial imagery of smoking cigarettes and skinny models. So to see yourself reflected in a brand has been really important for our approach at Smash + Tess. It’s really built by the input of the community, what they want to see, what styles, what colors. I think the product is key for sure, don’t get me wrong. But I think what’s sustaining and building the momentum in this movement, which we call ‘The Romper Revolution,’ is the community.

And would you say that’s your North Star? Building community? You mentioned becoming an educator to build community, and even in the corporate sector, you worked with building company culture, which is community-based.

One hundred percent. With Smash + Tess, we’re focused on product, but we are guided by our values, If you never deviate from those values, you can create a community that’s so strong. That is what people come back for—it’s not just the romper. The rompers are fantastic, don’t get me wrong. But, for me, teaching and helping other people, giving back to the community that helped raise me, has always been something I’ve wanted to do

For sure. What’s it been like to watch it grow and build that community? 

It’s like a “pinch me” moment. I never take it for granted. I feel so much gratitude when I see someone’s wearing it [Smash + Tess] on their child’s birthday and they’re matching [with their kid] on such a special day and I get to be there, through our clothing. 

Don’t get me wrong, it’s so exciting to watch celebrities and influencers support our brand. But to be honest, it’s the daily sharing on Instagram where I get to see like, ‘Oh my gosh, I’m a part of your day-to-day or I’m a part of your special day.’ Those are the most “pinch me” moments, where I’m like, is this really what I get to do every day? This is amazing! And so I just feel immense gratitude.

I feel like you kind of answered my next question: has there ever been a ‘we’ve made it’ moment or is it all those little moments adding up every day?

I don’t think any entrepreneur would say that they’ve had a ‘we’ve made it’ moment because so much of what drives us, I think, is uncertainty, imbalance, fear. And those are things that we typically think of as bad things. But I think what we [entrepreneurs] all have in common is we never take anything for granted. We know that just as quickly as people loved your brand, you could lose those people. And so I don’t think you ever have a moment where you’re like ‘I’m kicking my feet up, I’ve made it.’ I think the reality is, is it’s a constant journey. And I think if you utilize and reframe that fear or that uncertainty as you evolving and becoming your best self, then it’s such an exciting journey. 

Generally speaking, I always say that it’s not that I’m smarter than anybody else, it’s actually that I’m super tenacious. I think by nature entrepreneurs are tenacious. We hear ‘no’ a lot, but we pick ourselves back up, we keep going. And so people like that don’t tend to sit in those celebratory moments for long, you just keep thinking of tomorrow and thinking of tomorrow. And honestly, that’s probably what makes an entrepreneur, an entrepreneur.

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And with your entrepreneurial journey, you’ve had your mom and your best friend by your side, helping build Smash + Tess. What’s it been like working with two other influential and important women in your life to build this?

It’s one of the best parts of what I do, if not the best part. I think being able to create together is such a gift. My mom’s, my mom. She’ll always be my best friend and my biggest cheerleader. And my best friend Mercedes has been my best friend since we were five, but what’s unique is that every day we get to hang out and just do what we love to do. We learn really hard lessons together and then celebrate together, even if it’s via Zoom with a glass of champagne. I think that being an entrepreneur can be a really lonely place to be. And I recognize that having incredibly strong, confident, powerful, smart women on this journey with me is unparalleled. It’s amazing. 

I’m very lucky for it and know that it’s not always the easiest thing in the world. Think about how you get along with your mom. Sometimes it’s like, ‘Why do you have to have an opinion on everything?’ but that’s what moms do, right? And with best friends too. Growing up, you fight over shirts, you get into squabbles, but at the end of the day, I think what’s enabled us to be successful together is sheer transparency, lots of communication, and openness. Being able to have that level of comfortability has helped us because the instant something comes up, we say what’s on our mind and then we move on. So, it’s not that it’s without its struggle, but the benefits far outweigh any possible challenges.

With Smash + Tess, you have been focused on A) being size-inclusive and B) being kind to the environment, using bamboo fibers and sustainable materials. We’ve seen these values become more popular in consumer-facing brands over the years, but it’s been important to your brand from the beginning.  Why was it so important to you to have these be pillars of your Smash + Tess from the get-go?

I think having a strong brand ethos is important from the beginning. And for us, as I said, it was always a community focus, but all of these things come from who we are. So, with being size-inclusive, we all know what it feels like to not feel welcome. We all know the pain of bullying, feeling like you’re not good enough, and we’ve all had different experiences. But I think, for decades, fashion has been a real culprit of making people feel like they’re not good enough. So, in my experience, rooted in just being a human being, I know how amazing it feels to feel welcomed and hugged and made to feel like I matter. 

If you met me, I’m a size 12. When I’d go to an event, I used to feel out of place. Like I wasn’t skinny enough and small enough and cool enough and all of that stuff. I thought to myself, like, ‘Why does it have to feel like that? Why does this industry have to feel like that?’ Women need clothes that are not so intimidating, that doesn’t make them feel that way. And so that part of that was from my experience of just being alive on this planet for 30 plus years and wanting to change that. 

On the environmental side, I grew up on the west coast and I see the beauty of this earth. I’ve spent my life camping and dirt bike riding and enjoying the beautiful place that we live in. And so that’s always been also something I’ve been conscientious of because fashion, fast-fashion, is another culprit [of destructing the environment]. We’re whipping out clothes that don’t have a demand that end up in the landfill or breaking down because they’re poor quality. And it’s just this vicious cycle. At some point, we have to stop and say enough is enough. So when we started Smash + Tess, and I wouldn’t ever pin us as an eco brand, but I do believe that we do things responsibly. Whether it’s the sustainable fabrics we use or our made-to-order, pre-order models, and even our carbon footprint—we put things on boats, we usually don’t fly things. We’re very conscious of how we are packaging. So, it’s just decisions you make that make us feel good and right, like we’re contributing and we’re not destroying. 

Being conscious of the decisions you’re making and making sure they’re for the betterment of everyone…

It’s being responsible! I think that’s what it’s about: socially responsible people. Why can’t we have socially responsible businesses too that think about the waste they create, that think about the people that they serve, who want to give back to their community and their economy and do what’s what feels right?

Throughout the years of Smash + Tess rompers, do you have a favorite design that you have come out with? 

One hundred percent. The Sunday romper—that’s our baby. That was the first romper design we ever made. And usually, when you’re creating clothes, you go through sample revisions, like three, four, or five times. With the Sunday romper, it came out, we tried it on and it was perfect. And that never happens! From there, the Romper Revolution was born. That’s what took off, that’s what people wanted. And that’s why we pivoted hard into rompers. So, it has to be our Sunday romper. It’s my baby. I think it inspired this entire movement. 

If you were to talk to other women who might be in your shoes with this great idea, but are maybe scared to change their careers, what advice would you give to them? To someone who’s looking to make a career change, but might be hesitant to take that leap.

It’s so hard because some people take the leap right from the beginning and they’re so courageous and they’re like, ‘That’s it, I’m quitting my job. I’m putting everything I have and I’m making a business.’ And wow, that is a confidence that I didn’t have. And everyone has their own journey. It took me two years of juggling both until I felt comfortable that Smash + Tess could sustain me and my lifestyle and my family. 

So every journey is so different, but I will say this, it’s all about action. You could sit on your hands and have a wonderful dream, and you might never realize that. You have to put one foot in front of the other and just go into action. That’s all I can say because it will then take on its own creative energy. It will inspire you to keep going, once you get going. I think standing still would probably really just take away from your potential success and realizing your dream. So I think first and foremost, just put one foot in front of the other. Just do it.

Following that, is there anything that you would tell yourself back at the beginning of this journey that you know, now that you didn’t know back then?

So much of my journey has gotten me to where I am now, but I think I would have said to sit in that imbalance a little more comfortably, knowing that it’s going to be okay. And I think it’s that fear that just paralyzes us, we can’t imagine a world outside of what we’re used to. We can’t imagine a different career. We can’t imagine a business being successful. And so, because we get so scared by that, it can put so much stress on yourself, with anxiety, and sleepless nights. I think I would have told myself to relax a little bit and just go with it and not be so fearful of the unknown, and instead realize that it means that I’m just growing and that’s a good thing.

And what does ‘success’ mean to you? 

Oh my gosh. That’s such a hard question. I think success for me is bringing joy to others. And as many people as possible. If I can continue to spread this and grow this and make more women feel joyful, then I will be a happy woman.

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