Rebecca
And Bec — two very different sisters who come together to reframe some of life’s big and small problems. We’re moms, writers.

Natalie
We have soft boundaries. We see the world differently, but we both lean into vulnerability together and with our guests, because we like deep dives. So come with us — let’s reframe something.

Hey, Bec.

Rebecca
Hey, Nat.

Natalie
Did you know that we have officially hit 100-plus episodes of Reframeables? Congrats to us!

Rebecca
Indeed! Feeling accomplished.

Natalie
Resilient even.

Rebecca
Yup — which has prompted a new theme for a six-episode series.

Natalie
A mini-season, if you will.

Rebecca
Female-focused resilience.

Natalie
With some fascinating guests, from Indigenous brand founders to CEOs to philosophers, we work to reframe resilience from a variety of perspectives. We know you will laugh, you will get inspired, and you will be compelled to dig deep for the resilience inside yourself.

Natalie
Wow. Those are some bold claims, Bec, but we do stand behind them 100%.

Rebecca
So here we go: our first guest in the series, founder and CEO of Cheekbone Beauty Cosmetics, Jenn Harper.

Natalie
Cheekbone Beauty aims to help every Indigenous person see and feel their value in the world while developing sustainable colour cosmetics that won’t end up in a landfill.

Rebecca
Jenn has been featured as Chatelaine’s Woman of the Year in 2019 and was on Canadian Business’ New Innovators list and Entrepreneur Magazine’s Woman of Influence list in 2022.

Natalie
So here’s our conversation with Jenn Harper.

Rebecca
I heard you say on Breakfast Television that the company itself came to you in a dream.

Jenn
Yeah.

Rebecca
And I just wanted to touch on just this idea of dreams and storytelling and how that has been a thread for you in Cheekbone success. So can you talk about that a bit?

Jenn
Yeah. So as mentioned, I was, like, in the food industry. That’s where my career had always been — whether starting out in hospitality, and then sales and marketing in the food industry. Broadline distribution with Sysco, and then went to just work for a seafood company, and I was selling fish and then in 2015 had this dream of, like, three native little girls covered in lip gloss, and woke up and started working on what is now Cheekbone Beauty. But of course there was a massive year span.

I always share that it’s like… people, they’ll hear that story, but I’m like, “Ok, if you knew all of the behind the scenes things,” — like, in my life there was all of these crazy things happening. So newly sober — I have this dream two months after getting sober. And I’m also learning, like the rest of Canada, about the residential school system, but also learning that both of my grandparents survived that. It’s something my family had never talked about.

Natalie
Wow.

Jenn
Meanwhile, I’m like: I always just thought my family was dysfunctional and didn’t know why. And for me, learning about the residential school system, and that was my grandmother’s experience, really was eye-opening. Learned the term generational, or transgenerational, trauma, and how that can exist in our DNA for generations, and understanding who she was after that school — like, she was taken at six years old. When you have kids and you hear that, you’re like, “Wow, how does that happen?” And then learning even now, like, how the kids that were taken from their families, the trauma exists because they’re blaming their parents. Like, “How could you let this happen?” But meanwhile, their parents are being told by the authorities — like, they’re telling you this is what has to happen or you go to jail, and we’ll take your children anyway. Like, there’s so much fear, and understanding that and learning all of the details and how those systems really not only were impacting my family back then, but still exist in many ways today for many First Nations, Métis, and Inuit people.

And so because I had this new information, I really feel like it was like this ‘a-ha’ moment, and I really wanted to do something to support my community. We’re always tired of hearing the negative stories, which are in fact true, but I was like, “What if I could build a brand that did this and help support, you know, through this scholarship fund that I dreamed about? And what if people saw themselves represented in a new way?” You know, thought about my own youth and never seeing another Indigenous person, let alone even from my nation or tribe (being Ojibwe), like, doing something in the world space and on a higher level where you could feel like you have opportunities. That just didn’t exist for us.

And so I was like, “Through brand, I think this is possible.” I really believe that on this unconscious level, we have no idea how important and how powerful representation truly is. You know, like, I really don’t think as humans, we fully have understood that until years of late — like, that when people do see themselves, you feel like you belong. And we’re recognizing that at Cheekbone Beauty — that, wow, you know, the feedback we get from community. When I’m out doing work in the public and you’re just hearing stories of people, you know — and not only just in the Indigenous community now. There’s so many other ways, like women in business — like, I’m at an event and this doctor who, you know, has been practicing for years, but has a business idea, and she heard me speak at an event and she’s like, “I literally just quit my job because of your keynote.” And I’m like, “Oh boy. I hope that’s all ok.” I’m like, “Wow, now I feel super responsible.” And she said, “What you said was we’re all led to believe that we’re not maybe qualified or capable of these things as women sometimes.” Like, “Was this the messaging we’ve been receiving all along?” And so when you really understand that the systems maybe aren’t always designed for certain groups of people, but you can break the rules and change things and do things your own way, and really literally follow your dreams. And so it’s been incredible on this path how I’ve just seen that — wow, on so many levels, representation is so important.

Natalie
So I’m going to just hold up my evidence.

Jenn
Oh wow.

Natalie
Is this an older package?

Jenn
Yeah.

Natalie
Because this is definitely older. Ok, so I, for anybody listening and not seeing any of the clips of this right now, I am holding up a Cheekbone Beauty lipstick that I got when I wrote in to a Hannah Sung newsletter. And either she had bought some of your makeup and then was now doing it as a promo to amplify your brand — because this was a while ago…

Jenn
Yeah.

Natalie
Right?

Jenn
Yeah, that is our original paper packaging which would have been launched in, like, 2020.

Natalie
Oh, ok.

Jenn
2020 or 2021.

Natalie
Ok.

Jenn
I think 2020, though — yeah. If I’m, like, remembering correctly. Yeah, and we’ve done so many different kinds of collaborations and promos, so I don’t even know…

Natalie
Who that one was with?

Jenn
Yeah.

Natalie
I know that’s where I got it because I remember getting it and it was sort of my introduction to her and her amplification of female-owned business, and… Anyways, that was kind of an exciting one for me. So I felt very au courant in terms of having your work there. But then I went and looked up the name of it, because it’s a really wonderful red. So I looked it up online and it says… it’s spelled M-A-K-O-C, but it’s said… ma-ko-che? Is that how I’d say it?

Jenn
“Makoche.” Yeah.

Natalie
And I love it. But now I just learned that I could get refills.

Jenn
Yeah — but not for that packaging. Yeah.

Natalie
Oh, ok.

Jenn
Yeah.

Natalie
Ok, ok, ok.

Jenn
Our refillable packaging came out in… I want to say 2023? And so now everything comes in refillable packaging. Yeah.

Natalie
Which is amazing.

Jenn
So we moved away from paper. Paper is porous at the end of the day, and so some formulations don’t last as long in them and we’ve noticed, like, all kinds of different issues. So we chose a more secure kind of packaging and then wanted to explore refillability.

Natalie
Yeah, which is more sustainable, and obviously fitting with everything that is Cheekbone.

Rebecca
Can you get that refillable at Sephora?

Jenn
So Sephora doesn’t sell our refills, but they can all be purchased from our website, yeah. They sell, like, the main unit — like a lipstick shade. You can buy any lipstick shade, but then if you wanted to, you can add a refill from our website. Like, I like the idea of knowing, too — because of our packaging and the way it is now, you can buy one shade in a regular component and then literally go to our website and buy two refills, or three, however many you want. And you can interchange them based on the main packaging. So say one day you’re wearing the haki, which is a hot pink, or aki, which is a great red, or makoc, you can just change out the unit because each refill comes with a tiny little cap as well. So you can, like, just use it as you need it, right, and pop them in and out.

Natalie
Right.

Rebecca
Cool.

Natalie
I love that. Ok we’re jumping, like, so deep in that anybody who’s listening…

Jenn
We’re so into product.

Natalie
We’re in the science here. So why don’t you give folks a little bit of a background, specifically starting from your Dragon’s Den experience. And I only say that because I’m a bit of a TikTok person these days (well, it’s been a while now) and I’ve been getting all these Dragon’s Den episodes sort of sent my way. And so when I saw one with you — like, it was a tiny little clip of it, and then I saw on Instagram your sort of eight-year business celebration, which brought back that memory of Dragon’s Den and how things have gone since then. I think people might enjoy that story, if you don’t mind.

Jenn
Yeah, for sure. So, you know, started Cheekbone in technically, like, a corner of my basement in 2016. And the business was operating as, like, a traditional e-commerce. That whole world gave, I think, a lot of small businesses a new opportunity to highlight and showcase their products. And then in 2019, I auditioned for Dragon’s Den in the spring. They always do the auditions in the spring and then the show airs in the fall. And so we were on season 14, the season premiere. So episode one, and definitely a big pivotal moment for the brand of getting recognition. We were doing a lot of business, you know, in the US and in Canada back then, but because of that moment it really skewed our business to mostly Canadian, because obviously you know how this platform where Canadians are seeing everything. And so it was definitely a time where we saw a lot of newcomers to the brand, and a big growth moment for sure.

But the behind the Dragon’s Den story, that was the third time I had tried out for the show, which is really interesting. And when I give my public keynotes I always share that, because it’s really important to understand that nothing happens unless you’re, I don’t know, abnormally successful or super lucky, ever on the first try. And even when we did get the opportunity to go on the show, I just really recognized how far I had come as an entrepreneur, how far the business had changed.

And then the new path that I wanted to take the business down, that was sort of the birthing or inception of this new version of Cheekbone becoming a sustainable brand, which is very interesting because none of that was, like, even on that episode that aired, but it was like I was showcasing, “Ok, this is who we are.” This is how far we’ve come with products that we’ve had no control over in formulating. These are all coming from a white label, private labeller, but this is where we want to take the brand now proving for selling items in an e-commerce for three years that there was an appetite for this brand to exist. And so that’s why we were seeking investment.

But what many people don’t know is prior to that audition in the spring of 2019, I had started engaging with Raven Capital. And Raven Capital is the first Indigenous investment fund, or social-led investment fund, that has existed anywhere in the world. And these were three gentlemen that were really just starting out on their journey of building their business. And thankfully, because they are the ones that ultimately ended up investing in us, they gave us a term sheet before going on the show, and so I knew I had another opportunity to continue to grow the brand.

Natalie
Because wasn’t the whole thing of the Dragon’s Den experience that what they offered wasn’t what you wanted — like, it didn’t fit?

Jenn
Well, there was one offer that came. Going on the show, you know, talking about doing research, you really learn they hate beauty. They hate beauty brands.

Natalie
Oh gosh, really?

Jenn
Yeah, I knew that going in.

Rebecca
Why? Like, is it because they hate women?

Jenn
No, because it’s so easy to start a beauty company, technically.

Rebecca
Oh.

Jenn
Yeah. It’s not as challenging as the world might think. So think about this: I’m selling fish, I start this company, and I was literally buying lipsticks and lip glosses and these contour palettes from an organization in Toronto. Really low minimums. So anybody that you see that has a skincare line, haircare line, cosmetic colour line, I can 100% assure you they have no control over the manufacturing or where the products are coming. They’ve just started a brand, right? But these products are coming from a white labeller or private labeller. That’s what this is called. And it really makes entrance into this space very easy. It’s very attractive for people because the margins in the beauty space, they’re great. However, to actually grow and be differentiated from what the world has…

Technically the path we’ve chosen to go down was really learn about sustainability and incorporate this idea of Indigenous beauty along that journey, and really formulate — like, I started with making my own lipstick and moving away from completely private label, and we did that by 2021. And so we were not the same brand that we had started with, but that’s why investors hate it because the barrier to entry, there basically is none.

Natalie
Wow.

Jenn
Yeah. So just if you randomly now see a skincare line and you’re like, “Oh, I don’t recognize this. Where did this come from?” It’s likely someone that started a skincare brand, but they’re buying manufactured goods from somebody that’s been making manufactured goods for a long time. And quite likely, you know, there’s only so many manufacturers in the world. And so a lot of brands are just reusing the same formulations to sell. And you’ve probably have heard that before — like, L’Oreal, which owns, like, Lancome (and this is always, like, the best example), they talk about their mascaras. And, like, a Lancome mascara is technically the same thing as a L’Oreal mascara, it’s just different packaging, different branding, right? Because they’re probably coming from the same manufacturer. You’re just paying a different price point because the Lancome is perceived as more higher end.

Natalie
Yeah.

Rebecca
So there’s a lot of duping in makeup then.

Jenn
Yes. So there is, and then now in the world of TikTok, you have people like, “Oh, I found a dupe for this.” The truth is you need to really look at the ingredients list, and be comparing apples to apples to ensure that that is a true dupe. There’s so much misinformation even in that space, right? They’re like, “I found a dupe.” And I’m like, “Well, these ingredients are extremely inferior compared to this brand’s ingredients. So maybe for a colour you found a dupe, but it’s not the same product, right?”

Natalie
And then another post that I saw: you were speaking specifically to Indigenous entrepreneurs. And I really appreciated these lines, where you said, “Stay curious, keep learning, and trust your instincts.” Because to trust instincts that have not necessarily been amplified or presented in stories that sort of are recognizable — how do you trust? How do, sort of, you find that space inside yourself to trust for that doctor to go and make a big change in their life? That’s a scary place to go. So, I don’t know, how did you learn to trust your instincts?

Jenn
Listening to your gut is critically important, because I’ve made some bad decisions by not listening to my gut. So that’s excellent advice — like, always listen to your gut. But I really do believe there is some people who are maybe made a little bit differently where they don’t let fear or these things hold them back because yeah, entrepreneurship is certainly not for the faint of heart. Like, you have to constantly live in this space of, like, the unknown and it’s never comfortable. Like, if you are interested in a comfortable life, this is not the path. But then for me, that’s exciting. Yeah, there’s so much scariness and fear, but I think I thrive.

Which is, trust me — fear as a therapy, this is possibly not a good thing. Like growing up in trauma, maybe this is why this is ok. But I’m being real, right? Like, recognizing that this isn’t for everyone because of certain circumstances, but this is what makes me excited for the everyday, right?

Rebecca
Sometimes people ask us if we make money doing this podcast. The answer is we don’t. In fact, every hour we spend on Reframables is time not spent at a paying gig. And the steps to making a podcast are actually many. Finding the guests, booking the guests, reading the books, planning the questions, editing the interview, uploading it into the podcast world, making the artwork. So if you value this podcast, please consider supporting it with a financial contribution. Memberships start at $6 a month on Patreon and include a monthly extra where we record our five things in a week. In this world we have to support what we love, and with that support an energy comes back to us — so thanks for going to patreon.com/reframables and becoming a supporter. It doesn’t really make a lot of sense to be making a podcast, but here we are, three years later, still doing it with your help. So go to patreon.com/reframables — now, on to the show.

We’re trying to get into resilience on this series that we’re doing right now. So, I mean, it sounds like you are a hugely resilient person. Do you see yourself that way?

Jenn
I do. Because I’ll look back — in particular, there’s been a few years in the business where you’re like, “How did you survive that?” right? I’m personally very spiritual, so I don’t rely on myself always, right? And especially being in sobriety, it’s always looking to that higher power to carry you through, and that level of me recognizing that the creator of the universe and all the wonderful things of it — like the earth, and everything. You know, I’ll just start going through stats of data about how massive this all is. And then… no, I don’t have to worry because I’m being taken care of by the creator of the universe — like, legitimately. And so for me, it’s my spirituality that absolutely gets me through those really difficult times.

Rebecca
And when you say ‘the stats,’ what do you mean?

Jenn
How small our galaxy is in comparison to actually what’s out there. The fact that when you think of even creation on planet Earth, the perfection of this design is mindblowing. Like, you know, a few centimeters further away from the sun, we’d all freeze to death. A few more, we’d all burn to death. Like, this is perfect placement in the galaxy. Then based on, like, so many things that humans have no control over any of these things. This is how it was made, for us to thrive and live here. We’re like this race that this was made for us. And so it’s just the details of all of that. And I spend a lot of time in nature, and you recognize that even in the winter when I don’t see where these birds are getting their food, but they’re still eating and being taken care of. Like, those are the things that help me live through a really difficult moment.

Rebecca
Oh, that’s cool. Our dad, he speaks with a lot of that language, wouldn’t you say, Nat?

Natalie
Absolutely.

Rebecca
Very connected to nature and the bigness of nature, and I think that’s…

Jenn
It’s so healing. Like, it really is. And then you just recognize that, “Ok, I’m a part of this.” And then there’s reasons why you shouldn’t have to really worry or get overly anxious or excited about things. Because at the end, it’s all going to be taken care of.

Rebecca
Yeah. So then in that sense, resilience, this is kind of a daily act for you. It’s not like you had one hurdle and that’s…

Jenn
No.

Rebecca
This is, like, a practice of gratitude, I essentially hear — and resilience.

Jenn
Every morning. Yeah. And when people ask, “How do you start your day?” Well, it’s literally outside and doing something physical — in prayer, meditating on all the things that help me continue to survive. And then recognizing — it’s like, they do teach us, I’m in my early journey of sobriety. Started AA, but never continued it just because I felt like I was too busy, but found my own path of how this works for me. And that’s, you know — all I need to worry about is today. Legitimately, right? Like, even in business, as much as we’re projecting and planning things for the future, but to keep myself grounded and at peace and balanced, it’s like, “No, really what is happening in this day is all I can technically manage.”

Rebecca
But does that actually make you a really good leader — like, in your company? I would think it would because you would be, as you sort of say, grounded in “Let’s not freak out people,” — like, I could see you saying something like that. Like, is that?

Jenn
No, because I still think I’m normal. I do panic, right? And at those moments of like, “What is happening?” But then, you know, it’s when you pause and you meditate on “You don’t have to do that,” right? It’s ebbs and flows for sure.

Natalie
Oh, well, I bet you if we asked your team, they would say, “No, Jenn’s really actually exactly the kind of leader we need.” But that’s interesting because you have definitely emphasized in any of the stuff that parasocially we feel connected to you, in terms of all of these, you know, like, online sort of spaces, you seem very team-driven. And recently you posted about seeking knowledge from community, and building a resilient support system where you share experiences with others — as opposed to, like, to others. It’s very much a with-ness. And I feel like that’s something that certainly hits home for us as sisters, Rebecca and me, but also for, like, what we’re trying to do with Reframeables — it really is about community building.

Jenn
Yeah.

Natalie
Like, in terms of your own community-building, yeah — your thoughts on that?

Jenn
Well, just learning as much as I have over these last 10 years, just about my culture and how it’s really community-driven — and physically, in experiencing that. In the early days, it was just me, but the Indigenous women’s circles that I’ve been a part of, their support, and when I’m having difficult challenges, they are always there — like, always, always, always. And it’s like these different networks, you know, from coast to coast to coast in Canada. There was a name we had a few years ago for, like, these conference buddies, right, that you really have formed these strong relationships with. And you know, when you, like, really know people want you to succeed and they want what you’re working on to succeed? Like, that is felt.

And of course, I mean, there are some situations where maybe everyone in those groups aren’t with the best intentions, but you know the circle of people that are there, and you can feel that on, like, such a deep level. Like, I truly feel like Cheekbone has been successful because of those groups. And that is a cultural thing. I really see within our communities how it’s this bigger picture thinking — like, we’re doing this. And the more we do things together, it’s more beneficial for the group. Unfortunately, you know, Western versions of business and colonization where you see people start to battle things out and you’re like, “Oh, that’s really not how we do things traditionally.” And if we stuck to the traditions then things would look a lot different. I’m so fortunate to have been surrounded by so many of these women starting in the very early days of Cheekbone that are still here that that’s what I felt. It’s like this force — this, like, team of women that you have and that have your back.

Natalie
Oh, that’s so lovely.

Jenn
It’s like nothing I’ve ever experienced in business before, to be quite honest.

Natalie
Wow.

Rebecca
And they’re all in different areas of business?

Jenn
All different areas of business, all different nations and tribes. Like, it’s really interesting. Yeah. I shouldn’t say even just Canada. You know, last February, I got to go to New Zealand with the Indigenous women groups in New Zealand, and I feel like now they’re a part of the circle. And of course, all over the US have met so many different organizations and groups as well where they’re now in the circle, right? Like, my circle has just gotten bigger and bigger — technically, like, more global over the last few years.

But the original, you know, when it started, it was by NWAC, which is Native Women’s Association of Canada. And when I had the dream, I knew I had to find some, like, resources. Like, I didn’t know anything about business. Like, I knew how to sell products and have conversations with people because that was my career, but I didn’t know anything about building a business. And I was like, “There’s got to be a program.” And it turned out there was this 12 week program that they were offering, and I entered it. And that’s where I started meeting this group and it’s grown ever since and it’s incredible.

Rebecca
You were saying your previous world was food and selling fish?

Jenn
Yeah.

Rebecca
My husband is funny, because he’s in sales so he’s always trying to tell me that his business is the same as mine. So we’re in TV, that’s another part of our world, and he’s like, “We’re all selling. Selling is the same.” So would you agree with that? Selling is the same if you’re selling…?

Jenn
100%. Yeah.

Rebecca
Ok.

Jenn
Your husband will probably say this: it’s about relationships, all of it at the end of the day, right? Yeah.

Rebecca
Yeah. So you agree.

Jenn
We’re all selling something. Think about it — our kids are selling stuff to us. Everybody has something, right?

Rebecca
That’s true.

Ok, just a little random. What’s something you never get to on your to-do list? Like, you know the to-do list when you keep transferring the same item from one list to another?

Jenn
Oh my goodness.

Rebecca
Is there something niggling at you?

Jenn
I want to drink all the water I’m supposed to every day. I feel like that one. I, like, look at the jug when I wake up in the morning, and I’m like, “Oh, I didn’t get through all the water yet.” So that’s always there. Trying to do more, but that’s a challenge. And then, yeah. I feel like I’m pretty good. I’ve learned to, like, what’s the word… Put the list together that you know you can accomplish, versus the one that you’re trying to. So I’ve gotten so good at that over the years. I’m trying to think in the past, like, what was always moving? And it’s always the hardest, most difficult one item. Yeah.

Rebecca
Yeah.

Jenn
The thing that would take the most, I would become the biggest procrastinator of that. Like, you know, building out the sales strategy for 2025 into 2026, like…. And that has to go into a document. And these are things I hate doing, right? So, like, stuff like that is what gets pushed as long as possible. Yeah.

Rebecca
That makes sense because the one I keep pushing is: get back to your novel.

Jenn
Oh, you don’t finish your book.

Rebecca
Finish your novel.

Jenn
Oh, you’re writing a book.

Rebecca
Yeah.

Jenn
Oh, so cool.

Rebecca
So it’s, like, very large to go on a little to-do list. Yeah. So I get that.

Natalie
Yeah. It’s sort of like a standing appointment.

Jenn
I’m writing one, but I hired a ghostwriter. I’m not a writer — like, the whole book would be written with AI if I was to do it. So I’ve hired a ghostwriter who actually works for Cheekbone to actually write the book. Because for us, we love our speaking events, it’s where we’ve created a ton of brand awareness. I was like, “What would get us more speaking events?” We always know it’s like a book or a movie. I’m like, “Well, we can’t do a movie. So what is doable at our level?”

Rebecca
Right. So you’re going to do a book about, like, the brand? Or it’s about your life?

Jenn
Yeah. So Caitlin was excellent at the outline — because I was always like, “Oh my goodness.” Like, I wouldn’t even know where to start with an outline. So it’s, like, my story, personal journey that got us to building Cheekbone, and then the Cheekbone build, and then (I think this is excellent because I never thought of doing it this way) — but then this whole concept that we’re trying to integrate into the entire beauty world. It’s called Indigenous beauty — and how we’re trying to do that, and what parts of our culture that we have pulled in to actually make that happen, and how we want Indigenous beauty to be, like, synonymous with sustainability.

Like, if you’re choosing that kind of beauty, those are the choices you’re making. And then if you think of, like, other cultures — like, we all know Korean beauty, people think skincare and, like, glass skin, and French beauty is, like, red lipstick and perfume, and all of these cultures around the world have their sort of concepts of beauty. And we’re trying to create this one for Indigenous beauty. And so that would be sort of the last section, which would leave us open to, like, hopefully more opportunities as well to expand on it.

Natalie
You were just promoting this pop-up that’s down at the Eaton Center downtown right now, right?

Jenn
Yes.

Natalie
Do you want to say a little bit about that? I was telling my niece about it yesterday. Her grade 11 English class right now is the Indigenous Literatures course, which is pretty amazing. So I was like, “I bet you your teacher would be kind of impressed that you are bringing them this information about this pop-up.” Anyways, do you want to share a little bit about that?

Jenn
Yeah, so Aaniin is a brand that was, like, street wear. Started in Toronto by a young lady named Chelsee Pettit. And really started as I think an online platform and then doing pop-ups at Stackt Market, and this year was able to bring 40-plus brands together and do this pop-up at the Eaton Center. So it’s incredible Indigenous brands from all over North America. We’re the only beauty brand there, which is kind of funny because there is more, but she had a hard time trying to actually source, and people that would, one, have enough product… You know, this is a big deal for brands, and to be able to have enough product that would get them through the entire month, so we were definitely able to fulfill that. But yeah, it’s a place where you can literally try everything. We’ve brought them everything that’s on our website. You would get to try it in person, which is really cool.

Natalie
That’s cool.

Jenn
And being at the Eaton Center, it’s just so busy. It’s such a busy mall and an iconic mall in Canada, right? So it’s a great place. And it was a really powerful moment when she had just launched and you walk in and you’re like, “Oh wow,” — like, this is so neat knowing all of these other brand founders and artists and creators have a place to have their goods. Because normally it looks really different for our communities — whether, you know, they’re selling stuff at an online store, but having a retail opportunity is huge. It’s really huge.

Natalie
Ok. So if you were heading down for the pop-up and you’re going be like, “Ok, I’ve got to get ready on the way.”

Jenn
Yeah.

Natalie
Which I did see one such video and I really loved it, and I was like, “This is why Jenn and I need to be friends,” — because I could do my makeup on the subway. What would be three to five components of your Cheekbone brand that you would keep in your bag to get ready to go?

Rebecca
Or, like, the steps. I like hardcore steps — like, tell me what to do.

Natalie
Yeah, Becca wants steps. Like a recipe.

Jenn
So if I was doing this super fast, it would be the Unify multi-pencils are going to be in the bag — like, two of them at the very least. Then the moon dust mascara, and the lip and cheek — like, the one that was like, it could go on your lips and on your cheeks. That was the colour that I put on because it travels so well. And then I even did eyeliner — like, I hope the team, they have the content. I was like, “You need to show that I just did eyeliner on a moving train.” That took a little bit more skill, but definitely the Cedar Brown eyeliner. So it would be the five items. So that it’s, like, got the whole face done in, like, I think it was, like, less than 10 minutes.

Rebecca
The Cedar Brown, that’s what I saw you do on Breakfast Television? Is that the one where you do it kind of messy?

Jenn
Yeah, you can. And it makes it super simple — instead of thinking you have to do these, like, perfect lines, and just you smudge it out and then, you know, set it so it’s not moving after, right? But then once it’s done, it’s good to go.

Rebecca
I love that. I think I’m going to go back to that, Nat.

Natalie
Yeah, I’m into it.

Rebecca
My daughter, my daughter who’s in grade 11, at one point, she helped me with a little routine, but it was all based on, like, what she does to herself. So it’s not like a 40-year-old woman routine. So there was no eyeliner or anything, but I think I need to move back to that.

Jenn
Yeah. And it’s funny, my daughter who is 19 hates lip colour, right? And I’m like, “Oh no.”

Natalie
Ok, yeah.

Jenn
I’m like, “I love colour.” And if I’m going to add it, it’s always going to be on the cheek or lip, right?

Natalie
Yeah yeah yeah. And I really feel like I need it. 46, I need some colour.

Jenn
Yeah. Without anything, I was like, “Whoa, wake up.” Then you put blush on and you’re like, “Whoa, I’m alive.”

Natalie
Yeah. Yeah yeah yeah. Then I can go out.

Rebecca
My mom will tell me that I look tired.

Jenn
Oh. Thanks, mom. Thanks a lot. Yeah.

Rebecca
She says it out of concern, which is, I don’t know, it’s…

Jenn
Yeah, and you’re like, “I just have nothing on my face.” Yeah.

Rebecca
No need for alarm. Ok, your best entrepreneurial tip, or your thing that you steer clear of? I mean, I’m sure you get asked this a lot.

Jenn
Wow. I do, and it’s interesting. I have a massive list now. You learn along the way. I think if I’m being truthful, I took investment too early and then you’re like, “Oh…” And, like, when you do it on your own, even if you have to take, like, a bank loan, you’re still the owner and you’re not impeded by anything that anyone has to do with your business. So that’s one thing — you know, as much as funding gets you into different places and to do different things, it’s just like, “What would I do differently?” And who knows? My next business, I might do that. You just don’t know, right? Like, those are things that you learn.

Rebecca
So just to say all of a sudden you’re beholden to somebody?

Jenn
You are. The moment you take someone else’s money, if it’s not a bank, and they’re an investor and want a return, generally like ours — you have to have a board now, and you’re definitely beholden to somebody else. So it’s like going into a marriage. You can’t just do everything on your own, right? So it could have been too early, or did I need it? You’re learning, like, so many things as you’re building. Possibly we wouldn’t be where we are without it. So there’s that as well. Like, I’m saying this in hindsight — like, I could have figured it all out, but I might not have without money, right? These are just things you learn. And I just want people to recognize. Sometimes I meet entrepreneurs and I’m like, “If you’re taking someone’s money, they want that back — and not just at the amount you’ve given them, they do want to return.” So you have to recognize that that’s a serious commitment and you have this now fiduciary responsibility, right, to these people.

And thinking you have to grow so fast — and that’s what happens when you work with investors. They want you to grow faster than sometimes is possible, right? So recognize you can build a really healthy, sustainable business and maybe it has to be slower, right? And I don’t want that to be like, “Yeah,” like, “Relax,” — because that’s not how anything grows either. But, like, it’s just it doesn’t have to be as fast as you think.

Natalie
I think that’s really helpful, especially for probably younger people who feel, like, a pressure to catch up with sort of a world that’s already going. But I would also say, as somebody who came out of one world of work into another, you know, in my 40s, it was an interesting experience to jump ship from one thing to another and then feel like I needed to be at the level I had been first. Like, in the other one here — when it’s like, “Well, but you’re new.” You have to take your time and do your learning. And I think, you know, it’s one thing to say it in your head, it’s another thing to feel that. So to hear it from another sort of learner in that way, I find that very helpful.

Jenn
And when you’re paying attention to, like, this ecosystem of building businesses and entrepreneurship, like, the stories that we hear are really unicorns. Like, those aren’t happening to the average everyday business, right? Like, that kind of growth. I was just listening to a couple examples this morning on a podcast — like, you know, Warby Parker or, like, Away Luggage and stuff like that. Like, those were born during, like, the digital era when everything was working implicitly well, right? And they went in less than five years to, like, billion dollar value. That’s not normal. That doesn’t happen to just every business. And so there was a time in the digital space when those things were happening more often. And everyone will recognize no one’s heard about those stories for the last, like, five years because it doesn’t exist anymore.

And so just paying attention to what you’re doing — and stay focused on, like, your lane. It can be really distracting and creatively draining if you’re paying attention to what everyone else is doing. Like, you need to focus on your business, your brand, and innovate on your items so you’re not looking at what everyone else is doing, because that can really be detrimental.

Natalie
Yeah, who said it? It’s a quote I’ve used lots of times, but “Comparison is the death of faith.” And I mean, whether it’s faith, you know, in a notion of a higher power, or in oneself, like…

Jenn
Yeah — or even believing something is possible, right?

Natalie
Exactly. Yeah yeah yeah. I think it’s a danger to steer clear of for sure.

Jenn
For sure.

Natalie
Like an ongoing goal.