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Buckle your seat belt, Ashley Freeborn, co-founder of Smash + Tess (insanely comfortable clothing, insanely growing company), tells her story of going from high school teacher to romper queen. Like many success stories, it was not carefully planned – Ashley and her company went where their customers rewarded them for going. There are so many great business and life lessons jam packed into this episode!

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Elaine Tan Comeau 0:00

It's time to create better, create better family health,

Announcer 0:02

business and self Welcome to Elaine's Kitchen Table. This is where we share tips about business and parenting. Being a mom of three CEO of the award winning company Easy Daysies speaker and educator, you're going to learn the tips and secrets of successful and incredible people. Elaine wants you to be inspired, challenged and motivated and that person you want your kids to grow up to be. This is real talk for real life.

Elaine Tan Comeau 0:31

Hi, welcome to Elaine's Kitchen Table where we talk about how to create better how to create better family health, business and self. And oh my goodness, you might not be able to see me right now but I am so comfortable and feeling so relaxed because I got this gorgeous smash and test romper on my body right now. And I also have this hot cup of coffee beside me and you might laugh I even lit a candle and I'm gonna show oh nice because I love the ambiance. And you know, I just I just love doing this podcast, and I'm thrilled to have my guests with me today she was born and raised in Vancouver. My guest Ashley built smash and test with her mom and best friend after recognizing an unfulfilled need a niche in the fashion industry for comfortable and stylish loungewear. Founded in 2016. Smashing tests has since grown from just two employees to a team of over 65 In just five years, and landed the eighth spot on Canada's top growth companies. In 2020. Now the co founder and CEO Ashley was named one of Canada's top 40 under 40 in 2020, and spearheaded several notable collaborations with celebrities such as Julian Harris, Sarah Landry and Hillary Duff. She is incredible. She wears her heart, but like on her sleeve heart on the outside, totally family oriented mom of two gorgeous baby girls and a wife to Mike. And I just want to say Ashley, welcome.

Ashley Freeborn 2:07

Oh, thank you so much for having me. I'm so happy to be here and hang out. We've known each other several years now. So cool to do this together today.

Elaine Tan Comeau 2:15

I love it. Like if I could have you here I would feed you some Malaysian food and yeah, and cheesecake.

Ashley Freeborn 2:22

Yes, yes. And yes.

Elaine Tan Comeau 2:27

Tell our listeners where you are right now.

Ashley Freeborn 2:29

I am in sunny Los Angeles and to be specific in the South Bay, which is all the beaches so I can't complain. It's beautiful out today. 25 degrees. I was saying Elaine, I'm not used to having a hot Halloween. So I'm used to being in Canada and wearing winter coats and, and you know, not even getting to show your Halloween costume. But it's beautiful, sunny, hot, and I can't complain.

Elaine Tan Comeau 2:57

Yeah, I wouldn't complain about sweating underneath your Halloween costume. Problem. For sure, Ashley, I want you to share with us something that you know many people might not even know it was there like something like a story from your childhood, like a time in your use where you remember that helped create who you are today. I'm not telling you in that rompers I'm just talking about most super woman that you are.

Ashley Freeborn 3:30

I would say the biggest thing and I always say this to working moms now who maybe didn't have a working mom. But the my I think that was most impactful as having a mom who was a career woman. She was in finance in the 80s and 90s. Working our way through leadership, she's now the president of a large financial institution here in Los Angeles, and having her as a kid to show me every day what it meant to wake up to go after what she loved to be truly passionate about something that maybe was outside of the household really shaped who I am today. And I think in the moment, it didn't feel like that, you know what it felt like was like, there's my mom and all the other moms are picking up their kids from school. My mom's not picking me up from school. She's still at work for another three hours or, you know, how come my mom is away and I have a recital and she can't make it and it felt difficult in the moment. But honestly, in hindsight, I'm like, I wouldn't have had it any other way. Because whether where they had instead is so much more. I think for me, it's like you can teach somebody how to be confident you can teach somebody how to go after what they want. But for me, I just watched my mom do it every single day. And so I'm grateful. I'm grateful for that experience that I had, even if it did kind of suck at the time.

Elaine Tan Comeau 4:54

I'm sure I'm sure you know like I was a former school teacher and I I hear you when, even as a teacher and I didn't have kids yet, and like, I knew that my grade one class, my grade two class, like when we had a performance, the only thing they cared about was finding their mom or somebody to wave to. They didn't sanely they totally messed up their part, but they didn't care all that was important, but it was for them to see someone they could wave to, and I totally get it. Do you ever like right now when you're like flying here for a meeting? I'm flying over there for a meeting and leaving your girls behind? Do you? Do you feel what you felt when you were a kid visit?

Ashley Freeborn 5:37

Yeah, and I think that's why I like to. I like to tell as many moms as I can, because I do feel that and like I funny story. There's this thing called trunk or treat mele and I have had such a busy work week I've been flying around all of October or traveling. I volunteered of course to be the trunk or treat mom, one of them. And I had never heard of this because I'm Canadian. And apparently it's a thing. Now I didn't know that I showed up today at the school ready to go. I'm like, what do you need me to do? Put me in coach and they're like, Well, you need to bring your card has to be decorated. You need to have treats luck, hopefully not candy, they should be healthy. I'm going to Oh my god. I am not at all prepared. So I randomly saw this car fully decorated to moms in typical, I'm not gonna this is gonna really rub it in for Canadians, but they were wearing bathing suit costumes, because it's that hot. And I'm like Moms, I'm like, listen, I signed up I have a feeling you're doing trunk or treat had no idea what I'm doing. And they both were like, okay, Mom, I got you one of them put a headdress on me. The other one gave me two Halloween blankets. The other one was like just gonna CVS it doesn't matter. Get candy, the kids will love it. Like, pull up next to me. I'll play Monster Mash the kids will love me like, okay, and so I'm into a bikini literally felt supported in this moment. And I'm like, this is where and you know, it was like it was honestly there were like, it doesn't matter. Like you're here. Your kids gonna see you. They're gonna be happy. That's it. End of story. We'll make it happen. And I it just was a reminder for me to be like, yeah, like, is it hard people say this all the time? Can you have both? You know, Can you can you balance work and work in kids, can you? And it's like, not always gracefully. That's the answer. It's not an easy task. And there's lots of times where I'm flying somewhere. And I know that I'm not going to be able to pick Frankie up from ballet. And I feel a tinge of guilt. And, but at the end of the day, I know because I lived it. I know that the long term effects of this as long as I'm when I'm here I'm here for her. And I am you know, I'm present I'm engaged I'm then I know that down the road, I have a feeling she's going to be a forced you know, because she's, and this is the other part that's so cool. i My mom used to leave for work. And I did too when I was a teacher but my Frankie actually gets to watch me work because I work remote so much of the time. And so not only is she seeing me, or knowing I'm doing what I'm loving, she's actually seeing me do it like she's actually like, and so it's so cute. She'll come up to me and be like, she'll go on or my phone is like smash and test people. And I'm like, I'm working on the financials right now. I'm very busy. I'm like, You're adorable. It's like it's important. We don't beat ourselves up.

Elaine Tan Comeau 8:23

It's don't beat yourself up. No, I totally understand. And when I first started Easy Daysies And I'd have to get on a plane to a toy trade show in New York. And I knew sometimes like, I'd be honest, like knowing that I was going to miss a dance recital or something. And I actually got like, emotional on that plane. And I like probably more than once because I remember the stranger beside me would say, oh, was this your first flight?

Elaine Tan Comeau 8:56

Man I just started saying yeah, sure. Yeah, it's my pastor. Oh, my goodness. Well, you are supermom and, and

Ashley Freeborn 9:06

things are gonna lie. I don't remember any of the ballet recitals my mom missed. I honestly don't. What I remember is my mom, you know how you matching PJs on Christmas? Crafting with my mom, I don't remember. I don't remember any of those little one off things that in the moment felt a little bit like a tinge of pain for me. I don't because another of it in the long run really mattered. So we gotta let go of some of that stuff as moms you know,

Elaine Tan Comeau 9:28

no, Ashley, I love what you said like just when you are there be fully present. Right? And that's the most they remember. And you know, like, after when I had a stroke and I had that stroke rehab for seven months. And you know, one of the lessons that I remember learning and profoundly was learning to be a master of single tasking and that meant putting my full everything into that relationship that I was spending that time with, you know, if I was with my daughter and my son my head Been, or at work, like, then I'm fully like, if I'm writing one email, you know, focus on that. And maybe, I mean, it just means learning to drop the balls. And it's okay. Because you know, how many times have I felt like I had 22 balls up in the air with my arms tied behind my back? I hate that. And you know, and I learned, it's okay. Let the balls drop. Just focus on that person you're with right now. Yeah, might suck. But you know, if those things are important, they'll come back, they'll those balls will float around. If they're

Ashley Freeborn 10:32

funny, you say that? Because I get this question a lot. And they're like, people are like, how do you nurture yourself? We have so many things going on, how do you take care of you? And I'm like, I am the worst. One piece of advice I got, and it's similar to what you're talking about right now is like, it's actually a form of meditation to be entirely present, even if that means it's an action. And so for me, I'm a go, go, go, go go, like Uber productive. I'm not and I'm not happy and less than producing. And so someone gave me a really good piece of advice. And it was like, that's okay. Like you do you buy it? See if you can, actually so you're in the shower, and you're washing your hair? Can you just think about washing your dishes, wash your hair, you know, and that, that is a way of actually meditating versus sitting somewhere and being like, I'm quiet. I'm zooming out because I'm, like, so bad at that. But when someone told me that piece of advice, similar to what you're talking about single tasking, it's like, Oh, okay. It actually does rest your brain a little bit. It actually does, like, make you more much more engaged and like, relaxed in a sense, right? So it's, it's, it's a it's challenging. It does.

Elaine Tan Comeau 11:38

It's like it takes training to do that, because I'm liking I'm really happy when I'm productive. Like, if I am Yes. Yeah. Like, it makes me happy. It's just like, I'm like, Oh, I got this done. I'm like, Oh, I'm gonna write a book.

Ashley Freeborn 11:53

Totally. It's like, you're doing what?

Elaine Tan Comeau 11:58

Now, okay, super romper? Queen, I have to ask you, okay, how did you get from being a school teacher? Which I think some people don't even know that you were, you have to tell us a little bit about that. Like, What on earth did you teach? And, and those people, your kids, those students are probably like freaking out that you are who you are today. So how did you go from school teacher to romper queen?

Ashley Freeborn 12:23

Well, I was a teacher for 10 years. So all of my 20s and I was a high school teacher. So I taught anywhere from like English. To theatre I taught. Yeah, a lot of theater. I finished my career doing I was a full time theater director at a secondary school and Whitlam gleneagle I think your kids go there. Oh, yes. Yes. So look at the Theatre Wing, you'll see like posters, it'll say directed by Ashley pretty boring. So they're

Elaine Tan Comeau 12:50

killing me. Okay. Do that.

Ashley Freeborn 12:52

Yes. And it like was the most amazing. Honestly, I just love my career so much. I love the kids, I love being creative together, I see flashes of what I do now then, like I, I recognize that what I loved the most was We almost ran our own business in theater, like we, as a team would put on these huge productions that we'd work all year for. And then we'd want to make money so that we could put that money back into our next big show and do it even bigger. And so I love that element of what I was doing. And but I always love fashion. And I think, I think if I if I look back when I was in high school, I didn't see a lot of young women entrepreneurs, that wasn't something that was on my radar. And so even though I love fashion, it seems risky. It seems like crazy. It seemed like what, you know, I wanted to go do something where there was a pension, and there was benefits and security and all that. And so remember, I mean like Instagram didn't exist, you couldn't see a 22 year old running their own brand. You know, like, literally you can see it now. And so I went into teaching and I loved it. But all the while I really wanted to do fashion and so I think it was finally in 2014 I went and did a summer crash course on my summer off in Conde Nast College of Fashion Design in the UK. Well, that's where the business plan was really born. And it was born out of a love of my mom and I we love matching pajamas. And so all year we would try to source the most the coolest pajamas for Christmas morning. And that's really what smash test was founded on was like, family, comfort, fun community. And so as awesome. Yeah, it just honestly, there's so many things I did as a teacher now that I'm like, Oh my gosh, all of those things that made up for my career now, primarily just a focus on togetherness and like a joint goal and creating something as a community. Like that's to me what smash says Oh, and we happen to make clubs but like really the strength of what we do is the community that we have.

Elaine Tan Comeau 14:57

I love that

Ashley Freeborn 14:58

I love that grew into One thing,

Elaine Tan Comeau 15:01

I love that you said that so well, right? It's not about rompers. It's not about great comfortable, like fabrics, that you know, I had your body, but it's about bringing people together and, and just celebrating that, like any person, like family community, and I love that. I love that so much. Thank you. That's so true. You know, I'm thinking of our awesome listeners who are, you know, starting out in their business or in it for years. And sometimes we get stuck on the, you know, the production and deadlines and shortage of materials, but we forget the joy side, which is, we're making someone happy, we're helping somebody bring family together, whatever that product or services that you're doing. And that is the fuel of an entrepreneur has to be because if we forget that, then it's a little bit stressful.

Ashley Freeborn 15:58

Yeah, exactly. loses the fun. Yeah.

Elaine Tan Comeau 16:04

Okay, I know that you're like just skimming over how you became a smash and test romper Queen lady, but I have more questions. So it's all good. But there's this quote that says, you know, tough times, never last but tough people do. And, and you are an example of this. And you, you make it look easy, and it is not. And if you could share Ashley, like one time you failed or hit rock bottom, you just want to throw in the towel. Can you think of one of those moments that you could share with us? And what was it? And what did you get out of that to pick yourself up and be where you are today?

Ashley Freeborn 16:48

Yeah, I'm think like that, gosh, I have one of those moments daily. You know, like, I honestly have moments where I'm just like, What am I doing? Like, this is so hard, and it's such a grind, and I'm tired. You know, like, I think you just get really tired. And I mean, I've multiple things from you know, huge production blunders where stuff comes in, and it's not at all what you, you know, had ordered or designed or wanted, you know, to Hillary Duff, you know, obviously saying no, multiple, not saying no, but through her people, I heard no multiple times. And I just kept seeing her wear the clothes. And I was like, oh, no, you have to do a collab with us. I can tell you love the brand. And, and you know, so there's lots of times you hear no, there's lots of times you feel like, Oh, this is not going to happen for me. And I think it's only tenacity that separates a successful entrepreneur, from the rest of the pack. You know, it really is just like, one foot in front of the other. Where there's a no, you don't sit on it, you've got to keep going, you've got to be like, Yeah, that sucks. Fine. If you need to grieve it, grieve it, and then onward and upward. And I think like, it's so easy to get stuck in those moments and to be down on yourself. And to think like, this is a horrible idea, and then your failure and all of those things. But the truth is, is that those those are the moments that make you a more creative entrepreneur, and they build grit, and that's what it takes to be successful. It's not easy. You know, my mom always said the lucky are the harder I work the luckier I get. Like people are like you're so lucky. It's like, actually work really hard. And yeah, so and I think that that, that there's a lot of truth in that. So I think that's what I always say is like, yeah, just it's literally because people are like, I have an idea. But I don't know that it's like you just have to put one foot in front of the other you really do every day. Just keep grinding it out.

Elaine Tan Comeau 18:44

Yeah, even for moving an inch forward. You're moving so

Ashley Freeborn 18:47

moving and ask lots of questions. Like I when I see like, people, there's a humility there that like I think I also see amongst successful entrepreneurs, it's like, it's okay to ask questions. Okay, not to know every answer to every question. It's okay to be like, hey, I want to work smarter, not harder. How did you do that thing? And like, I see that in common as well with entrepreneurs. Yes, there's creativity there for sure. And there's an originality but there's also like an open and willingness to learn and to, to kind of get to realize you don't know everything about everything, you know, but you want to learn.

Elaine Tan Comeau 19:22

Yep, I love love everything you're saying like tenacity, grit, and the willingness to learn, right? Like, yeah, don't be too proud to ask, like what you just said, Ask lots of questions. You know, like, if I could go back in time, I would have asked for help much sooner. And so do it. Now, if you're listening. Don't wait 10 years now. Yeah, I want to know, I have a question that I know that people have asked me to ask you and what was that first big break or turning point for smash into Was it like a collaboration? What was it?

Ashley Freeborn 20:04

Yeah, I think, a series of little things, but I think the one where I felt like, oh my goodness, there were several, there were several big milestones. One of them was the first time Jillian Harris were a romper. And the because before that we had a romper was one of many other different product offerings. And when she wore it, it sold out in like, a day. And it was a very pivotal moment for our business, because it was like, oh, no, we actually don't have any more stock. And then it was like, Oh, what do we do. And so we went into this pre order model, that's really how this through the last five years of us being in business, more of a sort of sustainable way of producing for the demand that you have. So that was a big moment, because also in that moment, we realized, whoa, women want robbers. And so we pivoted hard into the romper world, and kind of everything else kind of fell to the wayside as we really honed in on the product that we that we felt was going to get people most excited and happy, etc. So that was a really big moment. And then, of course, to close that circle, you know, years later years, maybe a year and a half later, actually, doing a collaboration with Joel was like, it was just a full circle moment for me in that like, and now obviously getting to hang out and chat and tell her like, Wow, you really need such an impact in my business. And but you know, that's, that's where I say the, the harder I work, the luckier I get, because you can have that kind of a moment. It's what you do from in that moment and forward that really counts. You know, like, I'm sure Jill talks about a lot of products, but what how do you as an entrepreneur, take that leverage that build off of that, right, like, and that also comes back to humility, it's like sure that I have all these other product offerings, yes. But like, whoa, actually, what customers want is this. And so it's like, okay, well, I'm gonna go into what people want. And I'm gonna, like, make a huge business change. And I'm going to into you have to just be open to like, life's possibilities. And just, you know, you never know which way you're gonna go. And yes, is it did Jill do amazing things for my business 150%. And I tell her that every chance that I can get, but it's really about the team that then ran with that, you know, like that opportunity, seizing it going hard after it, I think is what was kind of magic about smash and test.

Elaine Tan Comeau 22:35

That is awesome. That is awesome. And that's how humble you are. Because you're you you give appreciation and credit to where you feel should have. And that is very admirable about you, Ashley, you're awesome. Awesome. Now you also make collaborations look super easy. And I know it is not. But tell us how. How do you do it? How do you How does one even think of it? And what do you do?

Ashley Freeborn 23:04

I mean, we're the color the collaboration queens, I think we do one every month at least if not more multiple, they're not easy. But at the root of smashing tasks is a focus on on collaboration and winning together. And so I think like, for us being open to partnerships with other like minded individuals and brands, and is just first of all super friggin fun, you know, we have a blast doing it. And it's also it can be really impactful. If you're introducing each other to each other's communities, you know, it's really cool thing to be like,

Elaine Tan Comeau 23:41

is that how you would reach out to them?

Ashley Freeborn 23:44

Depends. Sometimes it's like an organic thing that just builds in, you know, and sometimes it's like, seeing people wearing your clothes and really being supportive of your brand makes you want to be like hey, like, let's let's work together. But yeah, there's multiple ways it's not, we have kind of a way we do it, where we like to approach our collaborators to be like, Hey, we like what you're doing. We think you're really cool. This and then we'll communicate it via like a deck where we say like, this is how we think we could work together. And we even give some creative ideas as to how what that could look like and then we kind of go from there. And we strike out a lot like if you knew how many pitch decks we've put together and how many people we've been put in front of and how many times I've heard the word no. You'd be surprised you know, but it you just keep you have to keep going. For every like 100 knows you're gonna get a yes, you know, so you just gotta keep going.

Elaine Tan Comeau 24:42

That's awesome. That's great advice, right? Like, yeah, that 100 knows you might get a yes. So true. Like Like even when we're selling a product or service, right? They say it takes seven to 10 touches before you might even hear back and don't take it personally. People are busy. People are busy. If there's stuff going on, everybody has so much going on. Now you lucked out and work. You're working with your mom and your best friend. What Right? Like most people will say, Oh, don't work with your mom or dad? Or don't work with your best friend unless you don't want to have that friendship anymore. Tell us what is it like to work with your mom and your best friend?

Ashley Freeborn 25:25

Oh, yeah. I mean, it's not easy. For sure. It's, it's a challenge. But it's so fun. And I always say like, the benefits far outweigh any of the challenges. I think like, clear division of responsibilities is very important. It's like, you have to know that and I believe so much in strengths based leadership, or it's like, what do you love? Like, what makes you tick? What are the things that you're like? Yes, I want to do this all day long. And then what are the things you're like, it might even be you're good at it, but you hate it. And then one of the things that you love, and you're like, Yes, I'm hitting my growth. This is where I'm like, creating the best product, the best version of myself like, and so and then, and then creating, you know, a division of responsibilities that's aligned with that with those strengths. And I think like, if you do that, then you're in a much better position. I think what can be clunky is in the beginning, as things start to build momentum, you start to be like, well, I thought I was doing that are you doing now but this is my role, like anything, you start to step on each other's toes. And so you think clear communication. I'm lucky because my mom and my best friend, like I've been friends with Mercedes since I was five. So she's a system to me. So it's really like a matter of like, Hey, are we weird right now what's going on? Like, our like, or it can be just like, you know, Merle loves something and I look at it like, I actually hate that I hate it. It's just like, not into it at all. And she'll be like, you're not you know, like we just have these really open honest conversations. And I think that's part of it is yes, division of responsibilities, but to is like clear, like lots of communication, just like being open to having tough conversations when they need to be had, knowing that we have the best intentions, right? Like, I think that's also it is like knowing that someone means so well and it's coming from a place of love and trusting in that bust. Yeah. And then you can then it's just a lot of fun like after that once you get all that stuff sorted out. It's like it's a it's a blast working with your mom and your best friend and but we have different roles. My mom's not in the business every day. She's doing her own thing. She's more of an advisor she comes in when I need her. Mercedes is very clearly on more of the aesthetic side doing lots of design photoshoots, etc. And then, you know, I'm, I'm on the hook, I'm on all the business performance calls Brian,

Elaine Tan Comeau 27:34

over the face, I would say the face the PR the

Ashley Freeborn 27:38

that too. I used to run marketing. I finally have an amazing VP of brand marketing who took that over, that I ran marketing for a long time.

Elaine Tan Comeau 27:47

Ashley is sharing so many great tips and strategies here but we're gonna take a pause, and we're gonna share part two, which you do not want to miss on the next episode. So tune in and catch her incredible marketing strategies. See you then. Bye for now.