Business Women Who Lead

7 Mom Entrepreneurs Reflect On And Celebrate The Last Year

A photo of Ashley Freeborn and her two daughters for Mother's Day

“Mom.” The three-letter word seems so small given the magnitude of all that she does. You see, “mom” is a lifelong best friend, a trusted confidant, a nurse at times, and a superhero all the time. She gives the best hugs and she offers the best advice. And while Mother’s Day only comes around once a year, she deserves to be celebrated every single day.

For the following moms, their role expands past the average scope—they’re not only building families but companies too. From fashion and beauty to women’s health and wellness, these mamas are shining reminders that women can have it all.

To celebrate Mother’s Day, Bay Street Bull asked seven mom entrepreneurs about their favourite part of building a business while building a family, the lessons they’ve learned during the pandemic, and what advice they’d give to other moms during this time.

From Bay Street Bull to all of the hard-working moms out there, Happy Mother’s Day!

Taryn Herritt, Co-Founder of The Atelier Collective

Taryn Herritt, Co-Founder of The Atelier Collective

Taryn Herritt is equal parts world-traveller and country soul with a fascination of the business world and a huge passion for supporting women in business. She is the Co-Founder of The Atelier Collective as well as a Business Broker specializing in small to mid-market M&A, and her greatest love is her young family. And their household is busy: her husband, Gil, is a Director in Corporate and Investment Banking, and with two young daughters, Emalyn (5), Audrianna (2), Taryn is more passionate than ever about advocating for the next generation of ambitious women.

 

What is your favourite thing about being a mom and an entrepreneur?

After a busy career in the corporate world, the biggest appeal to me when I became an entrepreneur was not having to choose between a career I love and the flexibility to spend time with my family. I wanted the best of both worlds and running your own business puts you in the driver’s seat!

How did you have to adapt during the COVID-19 pandemic?

This entire year has been about adapting, shifting, pivoting, and leaning into resilience! I’m actually trying to think if there is an area of life that I haven’t had to adapt in, haha! For me personally, it’s been about learning to roll with the punches and looking for the opportunity in every situation, even in the face of massive restrictions in our industry, school closures, and lockdowns.

What was your biggest lesson this past year?

I actually listened to a podcast the other day on the concept of Post Traumatic Growth, and how that shift can happen alongside Post Traumatic Stress. It was framed around the pandemic and how there are very few—if any—times in history when the entire world is facing the exact same challenge, even though we’re all experiencing it in different ways. I think it really stuck with me because we’re all in the “messy part,” and my biggest lesson has been endurance—and forced patience haha—when that finish line just.keeps.moving.

What was your biggest “win”? (Go ahead, gas yourself up, you deserve it!)

I’m so incredibly proud of our team and our shift to the virtual world! As a company in the events industry—one of the most heavily impacted by this pandemic—we’ve transformed the way we reach our community and have grown our business from very local to global. And it’s even opened up entirely new areas of our business! We are a deeply experiential events company that now not only runs our own events but also designs virtual events for some of the largest companies in Canada!

Any advice for the other moms out there working from home during this time?

The lines between work and family time have definitely become blurred as we take calls and send emails at all hours of the day. Is it a good thing that my girls see hard work in action? Or is it going to have lasting negative impacts because they see SO much of it? I haven’t decided which side of the fence I’m on. My advice? Trust yourself when you set your boundaries to protect your mental wellness and your family.

Angela Osborne, Co-Founder of The Atelier Collective

Angela Osborne, Co-Founder of The Atelier Collective

For more than a decade, entrepreneur Angela Osborne has anchored her business endeavours on creativity and innovation. With an affinity for writing, Ang prides herself on her natural storytelling abilities and has used this vantage point to design unique and memorable events. This vision translated directly to co-founding The Atelier Collective alongside her business partner, Taryn Herritt. Ang’s most proud endeavour is her family: her husband of 6 years, Mark, and her two young sons, Dreyson (4) and Keaton (1 ½). Spending extra long weekends at the cottage with her boys is undoubtedly Ang’s happy place.

 

What is your favourite thing about being a mom and an entrepreneur?

When it comes to entrepreneurship, having the flexibility to adapt your working hours to what works with your family’s schedule is likely one of my favourite elements! This year was Dreyson’s first year at school (albeit a strange year!), and I’m so grateful that I get to drop him off and pick him up daily! Seeing his face light up when he leaves the school at the end of the day and sees me is a feeling I will carry with me forever.

How did you have to adapt during the COVID-19 pandemic?

Working from home while having two VERY active boys under the age of four has played on my patience in ways I never thought possible haha. It’s definitely been a constant flux of adapting to the new restrictions and limitations, and it’s been particularly hard having to constantly adapt to these external forces for my boys. BUT, wow, have I ever learned that resilience is a muscle that I’ve been able to strengthen in new and creative ways, and I’ve been sure to tap into my sense of gratitude for what I have around me. 

What was your biggest lesson this past year?

Echoing off my answer from above, I think my biggest lesson has been one in gratitude. I’ve always been one to practice gratitude reflection through journaling, but it’s been one action that yields immediate positive results. Through the past year, we’ve encountered so many things we have absolutely no control over. But one thing we can control is our thoughts and our actions. So while it’s sometimes a challenge to tap into the mindset of gratitude, the lesson I’ve learned is that when I can get into that appreciative headspace, everything else seems just that much more manageable.

What was your biggest “win”? (Go ahead, gas yourself up, you deserve it!)

I have to agree with Taryn on this one! When March hit last year, our entire vision for what 2020 was supposed to be quickly vaporized in front of us. But we as a team got innovative in the way we could approach our business, particularly our signature event, and it ended up being our most attended event ever! We also got the opportunity to host some of my biggest heroes on our stage, including Elizabeth Gilbert and THE Mindy Kaling! Still in disbelief over that fact!

Any advice for the other moms out there working from home during this time?

Well first, I just want to raise a glass and salute all of the working moms out there! You are all superheroes and the grit and resilience that it has taken to get through over a year into a worldwide pandemic is applaudable. 

In terms of advice? Well, here is just a gentle but important suggestion… The time dedicated to that ever-elusive activity of “self-care” is likely slim to none, but if you can take time just for yourself during the day, it will pay you in dividends. Even if it’s just a quick walk around the block, or starting your day with a few pages in your favourite book, it will set you up in such a positive tone for the rest of your day. And taking care of yourself is so important to how you can take care of those around you!

Rachael Newton, Founder of nixit

Rachael Newton, Founder of nixit

Rachael Newton is married to Tom, whom she met in London in her late 20’s. They went on to have Dexter (6) and Quinn (4), and also have 2 cats (they came first, but don’t tell the kids). Together the family has lived in 3 countries and 8 different homes, with family spread from Asia to North America. She began her career as a lawyer, focussing on hedge funds, ETFs and ETCs. After Quinn, while on maternity leave, she began focusing more on their household waste and it was out of that focus that nixit was born!

 

What is your favourite thing about being a mom and an entrepreneur?

I feel so lucky to be an entrepreneur, particularly during this time. Whilst it has been challenging (to put it mildly), it has also given me the flexibility to be able to take care of my children during COVID. It’s meant a lot of late nights, early mornings, and not a lot of sleep, but I’m forever grateful I’m able to have a job I can do in my own time and take care of my family. 

How did you have to adapt during the COVID-19 pandemic?

I would say what ‘adapted’ most was my mindset. I had to let go of a lot of things. At first, I would try to keep the children constantly engaged, working when they were sleeping or eating. Ultimately, for me at least, that wasn’t sustainable. I stopped beating myself up and let them have far more screen time than is probably acceptable in “normal” circumstances. But it was essential for my mental health, and probably for theirs too. I took the same approach at work: I had to step back and, instead of working 24/7, just work out what was the most important task I had to do that day, get it done, and leave the rest for another day! 

What was your biggest lesson this past year?

I didn’t realize how much self-worth I derive from my job and my business. I’m truly proud of what I have done and the business I have built. I will choose my children’s health and welfare above everything, but I realized that nixit is actually pretty much my third child. At times (a lot of the time), I couldn’t give it the attention I needed to—which resulted in a lot of low points for me. 

I’ve worked very, very hard to get nixit to where it is, and at times, knee-deep in online lessons, crafting virtual Zoom tours, it all felt very pointless. When you have your own business you can’t just “switch it off,” but I had to do that at points and it was difficult for me. The silver lining is that it reinforced how much I care not just about nixit, but about menstrual health in general. I truly believe we are making a difference, busting taboos and stigma, and improving periods for everyone. This year I learned how much I believe in that, and how I will fight for it, no matter how hard it gets.  

What was your biggest “win”? (Go ahead, gas yourself up, you deserve it!)

Keeping my business alive during COVID-19! Incredibly, we also had some amazing wins during that time. We got into retail: Nordstrom, Wholefoods, London Drugs! My mission when I launched nixit was to bring the menstrual cup mainstream—and I think we’re doing a pretty good job.

Any advice for the other moms out there working from home during this time?

Don’t be hard on yourself. Need to use dry shampoo? Go for it. Need to throw an iPad to a kid? Do it. Frozen pizza for 2 nights of the week? Why not. This is … awful … and as much as I love my children and my family, I draw so much strength, energy, and self-worth from my job. There’s nothing wrong with that and if it means an extra already-made meal or an extra hour of screen time, ultimately the whole family is happier. 

Emily Hosie, Founder of Rebelstork

Emily Hosie, Founder of Rebelstork

Emily Hosie worked in corporate fashion for most of her career and officially left it to launch and grow Rebelstork across Canada during the pandemic—and while six months pregnant! Her husband Craig is a former professional golfer, with a successful career in medical sales. Together they have Hunter (3) who is non-stop and welcomed Piper (5 months) to the family in time for a global-pandemic Christmas. It might sound chaotic, but she would have it no other way!

 

What is your favourite thing about being a mom and an entrepreneur?

Being a mom inspired me to become an entrepreneur–it helped me find a creative way to take back my own time, which is what Rebelstork is trying to do for parents. By building a growing business that solves challenges for parents, which they can directly benefit from, is my favourite thing about being an entrepreneur. I also enjoy the flexibility of directing my attention to my kids when I need to, while at work. I can bring them with me to the office, and no one will question it! Most importantly I hope they see what it takes to build a business, and to inspire them to take a risk of their own one day.  

How did you have to adapt during the COVID-19 pandemic?

Some of the biggest challenges we faced were delays in shipping and staffing up during what has been a high growth period. Because people were spending more time at home during COVID-19, they began to re-evaluate their living (and working) spaces, leading to minimizing their stuff-burden—exactly the problem we are solving for. Parents were finally getting around clearing out their outgrown baby gear and didn’t have time to sell it online or meet strangers in different places during the pandemic. We took a chance and invested in the growth of the Rebby van fleet to pick-up more baby gear directly from the sellers’ driveways. Everything is contact-free, so it has been a win-win!

What was your biggest lesson this past year?

That it’s okay to “Let It Go!” (thanks, Elsa). It’s ok not to do everything, and to turn to convenient solutions to solve your problems. As long as I know I’ve tried my best to solve my problems, I am satisfied. 

What was your biggest “win”? (Go ahead, gas yourself up, you deserve it!)

This year Rebelstork has been able to raise significant capital and scale our business nationwide—an exciting step forward as we reach new audiences and build relationships with parent communities across Canada. What’s more, is that we’ve entered into some exciting partnerships with both national and internationally recognized brands which we will be announcing soon!

Any advice for the other moms out there working from home during this time?

Wow, it’s not been easy for any of us at the best of times, but these are the circumstances which we are dealt with, so let’s find a way to work within them. I found that my community of support was a huge help—and Rebelstork’s Baby Gear Trend Report also forecasts a boom in virtual communities for parents—they can be a safe space that allows moms to find alternative ways to connect or support one another and help maintain emotional wellbeing. I would say to be open to a new approach to solving problems or to hearing what your community has to say. After all, it takes a village, right?

Vivian Kaye, Founder and CEO of KinkyCurlyYaki

Vivian Kaye, Founder and CEO of KinkyCurlyYaki

Vivian Kaye is the Founder and CEO of KinkyCurlyYaki. She is also a business & empowerment expert, Shopify educator, and all-around great lady who is a single mom to a 7-year-old super-duper kid, Xavier. 

 

What is your favourite thing about being a mom and an entrepreneur?

My favourite thing is how it forced me to learn how to prioritize, create boundaries, and do self-care. In both worlds, it can be very easy to lose sight of yourself, so both roles taught me to treat myself better. 

How did you have to adapt during the COVID-19 pandemic?

KinkyCurlyYaki was crippled when the supply chain came to a halt in December 2019, except at the time, we didn’t know why. And then we went into full shut down in March. It was something I couldn’t control. So I decided to start showing people who had brick & mortar stores how to quickly pivot their businesses online and I started showing up more in my Instagram Stories. This grew my reach and landed me opportunities I hadn’t even dreamed of. 

What was your biggest lesson this past year?

My biggest lesson was to focus on what I could control: myself. 

What was your biggest “win”? (Go ahead, gas yourself up, you deserve it!)

Building a million-dollar business from the ground up while raising a good human being, solo. 

Any advice for the other moms out there working from home during this time?

I know you can’t focus. I know you aren’t as productive. Managing your business 9-5 and kids with barely a break is A LOT.  But you’re doing a good job!  

Ashley Freeborn, Co-Founder and CEO of Smash + Tess

Ashley Freeborn, Co-Founder and CEO of Smash + Tess

Ashley Freeborn is a mama to two smart and lovable girls: Frankie and Stella. She is also the wife to an incredibly supportive and loving husband: Mike. AND she’s the Co-Founder and CEO of Smash + Tess. They are pioneers of the Romper Revolution, encouraging every woman everywhere to say goodbye to waistbands, and hello to loving themselves! Smash + Tess make clothes to fit you, and not the other way around.

 

What is your favourite thing about being a mom and an entrepreneur?

Growing up, my mom was a career woman in the 80s and 90s in the male-dominated industry of finance. She SHOWED me what it meant to wake up every day and follow your passion. She modeled what it meant to do what you truly love in life (outside of being a mom). As a mom and entrepreneur I now get to instill this love in my daughters. They see their mom wake up and do what she loves every day and I hope that they will never question their own abilities and dreams. And in my line of work, I get to involve them—whether that is with the clothes I make for them to wear and try on, or the books and blogs I write about them, or the photos we take together. I am grateful that my work life and my family life converge in an authentic way where I get to infuse so much of my love for my children into what I do every day and vice versa.

How did you have to adapt during the COVID-19 pandemic?

That’s a big question—we had a premature baby during the pandemic which exacerbated an already challenging year. We have also been missing our family in Canada as we haven’t been able to come home since the onset of COVID. We have adapted by holding each other even tighter. We have had to create our own village to offer the support we’ve needed: friends, friends of friends, etc!

What was your biggest lesson this past year?

My boundaries, my resiliency, and my preconceptions have all been tested in unimaginable ways. I’ve learned about my own power and tenacity, and my own capacity to grow stronger with each passing day.

What was your biggest “win”? (Go ahead, gas yourself up, you deserve it!)

My biggest win was a team win. It was taking all of the challenges of 2020/2021 and reframing the challenges as opportunities for growth. We did that as a team at S+T and we did that as a Team in our family. At S+T, we grew 100% YOY in top-line revenue, we tripled our headcount, and we accomplished huge brand wins including our collaboration with Hilary Duff… all while experiencing unprecedented issues and hiccups with production, supply chain, staffing, and distribution logistics. If we can do this, we can do ANYTHING! 

In our family, we had a baby who required a month of hospitalization during the height of COVID in Los Angeles while juggling our toddler, all the while being separated from the majority of our family AND being the busiest we’ve ever been at work. My husband and I make a great team. I’m feeling all kinds of inspired by the power of teamwork. 

Any advice for the other moms out there working from home during this time? 

Try to find the silver lining. My 3.5 year old runs by my computer daily screaming while I’m in the middle of a Zoom call, but I look at the positives. I’m home with my babies, my husband is home with our babies, we are safe and healthy, we have a comfortable place to call home, and COVID-19 has changed the rules when it comes to working remotely. It’s been nice to see the families who support and inspire the colleagues, peers, and friends that I work with daily, grace our Zoom calls. We are all juggling a million things, and it’s time we find compassion, space, and understanding for working moms who are doing it all.

Janey Reilly, Founder of WeeSleep

Janey Reilly, Founder of WeeSleep

Janey Reilly is the founder of the sleep consulting business, WeeSleep™. Too many sleepless nights with her own son Chase led her to seek training from an internationally renowned pediatric sleep specialist, so she could help other parents overcome their infant or toddler sleep challenges. Since then, she has built a growing team of over 20 certified infant and toddler sleep consultants who have helped families as far away as New Zealand.

 

What is your favourite thing about being a mom and an entrepreneur?

Being able to work from the comfort of my home (in my Pj’s if I wish!), to be able to walk my son to school, to take time to exercise and cook as part of my day, and to be able to enjoy the work/life balance which, to me, is one of the healthiest ways to live not to mention most gratifying. 

How did you have to adapt during the COVID-19 pandemic?

My business has always been home-based so not much has changed except I have had to add two more roles to my list “Teacher” and “Daytime chef”. As a single mom and CEO, I have had to get even more organized than ever to juggle the new everyday “norm.” I have also learned that I am the world’s worst math teacher.

What was your biggest lesson this past year?

To understand and ACCEPT more than ever, that change and adapting is simply part of what we always do, every day, every year. This year it’s just been a surreal reality and the changes and pivots have simply had to be greater. However, at the end of the day, like my father taught me, we have to count our blessings we are still so very fortunate in so many ways.

What was your biggest “win”? (Go ahead, gas yourself up, you deserve it!)

I launched my digital training platform (which is killer I must say!), added to my Management Team, and gained more talented consultants! And I secured a GAME-CHANGING partner—stay tuned!

Any advice for the other moms out there working from home during this time?

Scheduling and planning are key! Map out your week and your goals to give yourself some direction and a sense of organization. 

Try not to beat yourself up if you give in to more screen time than usual or lose your S#%@ every now and again… We are human, we are only one person, and although it feels like we are drowning some days, it’s important we honour ourselves, our time, our self-care and our sleep and health needs. Things will not always go according to plan, and that is OK! 

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