We had the opportunity to speak with Ashley Freeborn, the founder of Smash + Tess, who discussed her reasons for starting the business, crucial factors to take into account for professional development, the value of developing relationships online, working with well-known influencers and celebrities, crucial considerations for female leaders, and the significance of equity, diversity, and inclusion in decision-making.
Born and raised in Vancouver, B.C., Ashley graduated from Simon Fraser University in Burnaby, B.C., 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 for 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 to a team of 50+ in six years. In the last fiscal year, S+T brought in $27 million in revenue, which was 26% YoY growth.
As CEO, Ashley oversees everything from designing to financial planning to dreaming up fun and creative marketing campaigns. Under her direction, S+T has grown exponentially in revenue and transnationally in market share and public notoriety. Passionate about creating clothing that celebrates femininity, strength, style, and comfort in women of all shapes and sizes, Ashley is also committed to giving back. S+T has spearheaded several charitable endeavors, raising tens of thousands of dollars to support organizations like Matriarch Movement, Mamas For Mamas, Marsha P. Johnson Institute and more.
In 2020, Ashley was named one of Canada’s Top 40 Under 40, which recognizes the most outstanding leaders in the country. She also led Smash + Tess through exponential growth, landing the company on The Globe and Mail’s Top Growth Companies for the past three years in a row. Ashley is a published author and her children’s book, Frankie and the Magical Romper, can be purchased at Chapters Indigo. She is also a celebrated presenter, touring North America to speak on topics including building a successful brand, e-commerce and D2C sales, authentic collaborations, and social media strategy.
What was your motivation behind founding Smash + Tess? And how will you describe your entrepreneurial journey?
We started S+T to shake up a typically elitist industry and bring fashion back into the hands of women everywhere, no matter their shape or size! We wanted to create a safe online space for women to build community, feel seen and represented, and to be celebrated. We started with a few items of clothing and a dream, and we’ve experienced rapid growth over the past 6 years we’ve been in business! Now we have over 320K IG followers, 180K email subscribers, and we’ve pioneered what we like to call “The Romper Revolution.”
Which elements do you consider to be most crucial to an individual’s professional development?
Mentorship is so important. Having other entrepreneurs, in particular women entrepreneurs, take me under their wing to help me make ‘fewer’ mistakes has been pivotal. Having a network of like-minded professionals is such a gift. They will celebrate with you when there is a success, commiserate when things are hard, and bolster you when you need a little extra support.
How important do you think it is to build relationships in the digital world? And how can you establish an online network and work with well-known influencers and celebrities?
Being digitally focused allows you to scale quickly and effectively. It also removes geographic obstacles, and in many ways, allows your community to be more accessible. Having a great PR firm to make introductions to influencers or celebrities is super helpful and it never hurts to reach out directly on Instagram. Personally, I always say “YES.” I say yes to invites to new digital networks, I say yes to podcast opportunities or mentorship opportunities. You never know where anything will lead!
What are the essential components that female leaders must take into account? How significant are equity, diversity, and inclusion in positions of decision-making?
Women need to know that we can dream big and we can dream actively. Having women modeling what it means to be a woman and be a leader makes it all more achievable. Having more women at the table will ensure we will help close the gender pay gap, ensure policies favor both men and women, and encourage further diversity in the workplace.
What challenges and possibilities will small business owners encounter in 2023? What are some possible strategies to take advantage of chances and get beyond obstacles?
We are in an extremely challenging macro environment at the moment, that is extremely promotional. Our inboxes are flooded with sales and heavy discounts, applying a ton of pressure on small businesses. Interest rates are continuing to rise, and life is expensive right now. I imagine 2023 will be more of the same. So, building a very loyal and supportive community base will help us weather the storm.
What specific advice do you have for striving women? And why do you believe it’s crucial for female business owners to share knowledge?
To be authentic to who you are. For decades, centuries really, women have tried to act more “masculine” so that we are taken seriously in the workplace. I say, being a woman is our superpower. Lean into that empathy, that matriarchal energy, it only helps us be stronger leaders.
