The Grit & Grace Leadership Podcast

Building a Beauty Brand With Purpose: The Story of Cheekbone Beauty with Jenn Harper

• Jen Kelly • Season 2 • Episode 16

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What if building a successful business also meant uplifting communities and protecting the planet? Join us for a transformative conversation with Jenn Harper, the trailblazing founder of Cheekbone Beauty. Jenn shares her inspiring journey from a life-changing dream to creating a beauty brand deeply rooted in Indigenous values and sustainability.

Inspired by iconic brands like Tom's Shoes and Patagonia, Jenn reveals how prioritizing people and the planet over profits became her guiding light. Learn how she navigated countless books, networking events, and the vital role of resilience and strong personal values in her entrepreneurial success.

Explore the profound connection between Jenn's Indigenous heritage and Cheekbone Beauty's mission. Discover how integrating the Anishinaabe seven grandfather teachings—emphasizing love, humility, bravery, and environmental stewardship—shaped the company’s path. Get practical insights into achieving B Corp certification, building ethical supply chains, and overcoming the inherent challenges of running a purpose-driven business.

Jenn also reflects on her evolution from an idealistic dreamer to a strategic leader, sharing lessons from her Dragon's Den experience and the empowerment that comes from facing personal battles head-on. Tune in to find out how passion, conviction, and community support can propel a brand to make a real difference. Don’t miss this inspiring episode—listen now!

Learn more about Cheekbone Beauty

Visit the website: cheekbonebeauty.com
Instagram: @cheekbonebeauty



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Jen Kelly:

Joining us today is Jen Harper, the inspiring founder of Cheekbone Beauty.

Jenn Harper:

We're putting people and the planet before profits, which in most cases in business it's really about. How are we, you know, filling stakeholder pockets versus actually taking care of those other things which feel far more important? But unfortunately, that's not how it really works in the business world.

Jen Kelly:

In this episode, jen shares her incredible journey of building a beauty brand from scratch without prior industry experience. Discover how her Indigenous roots and commitment to putting people before profits have shaped her mission and values as an entrepreneur. Let's dive in. So, first and foremost, we are all in for a treat. Jen Harper, welcome to the podcast. It is so wonderful to have you here. Thank you for joining us.

Jen Kelly:

Thank you for having me, in addition to your fantastic company. One of the things that I learned as I was reading up about you is that in 2022, entrepreneur Magazine named you as one of 100 women of the year, and when you actually look at that award, you are in great company and it's so wonderful to talk to you about entrepreneurship and leadership. So congratulations on everything that you've accomplished so far.

Jenn Harper:

Thank you so much. I am like a big believer in manifesting and I was on a flight and I remember reading this entrepreneur magazine in an airport in the U? S and started reading through it and there was all these incredible stories about people in business and I said when I got home I remember cutting out the top of the magazine and putting it on my vision board in my home office and the goal was one day to talk about Chic Womb Beauty in the magazine.

Jen Kelly:

And how much time had passed from that experience on the airplane.

Jenn Harper:

So 2016. So yeah, so quite some time.

Jen Kelly:

Well, let's go to the beginning of the company and your founder journey. What year was Cheekbone Beauty established?

Jenn Harper:

So we launched as like an online e-commerce store in November of 2016. This was like launched from a corner in my basement. I actually started the whole idea process after having like what I call like life-changing dream back in 2015. So I was selling seafood I worked for a seafood company at the time and it's January of 2015. And I have like this pop out of bed middle of the night dream. All I remember from this dream is three native little girls covered in lip gloss, with their brown skin and like rosy little cheeks. And I woke up that night and it was so real to me that this was like the next part of my life, even though I had zero experience in the beauty industry have never owned, operated a business Like it.

Jenn Harper:

It's kind of crazy when I think back to like from that dream.

Jenn Harper:

I was like, yes, I'm going to start this company, but the whole idea was I wanted to make a lip gloss from that dream, of course, and use a portion of the profits to do something to support my First Nations or Indigenous community.

Jenn Harper:

And I had no idea what that looked like, but I just knew. I was such a huge fan of brands like Tom's Shoes at the time and learning so much about Patagonia and their success and how really that this idea of like making a social impact was possible. When it came to business, I spent those first two years like just doing everything and learning so much about one my indigenous culture but two about entrepreneurship and building a financial plan, and I read over a hundred books between 2015 and 2016, trying to make sure that I was like learning as much as I could. I was just like an absolute sponge. I would show up at every sort of business networking event I could possibly afford or get to and try to make as many connections as possible, and that was definitely what the first two years felt and looked like.

Jen Kelly:

You speak to a lot of young entrepreneurs today. Do you feel like that leg of the journey is well understood in today's world, or are people a bit more impatient with how fast they expect things to come together?

Jenn Harper:

issue, because we see this idea of something becoming so successful so quickly in the online social media space and I think it's harder for us to recognize that everything is like 10 years before you really see true success. Because if you're going to do this, it's going to be this rollercoaster ride forever, and that's regardless of, like the revenue dollar amount, whether you're doing a million, 10 million a year or when you get to a hundred million, the ups and downs will always be there. I think it's just a numbers game and your problems just get bigger because of the size of the dollar value. But the problems are still there. They're not going away.

Jen Kelly:

What did you do to learn to cope and manage through the highs and the lows?

Jenn Harper:

What did you do to learn to cope and manage through the highs and the lows? The lows feel so low and entrepreneurship is kind of a lonely path. We choose it. I don't have a co-founder and I know even co-founders speak of feeling lonely because we're sort of all doing this from our individual spaces and so having a really strong set of values and principles just in my personal life has always been super helpful. A routine of great mental, emotional, physical and spiritual health has been critical. Meditation and physical fitness those are non-negotiables and no matter where I am in the world, that's how the day begins, and then I feel certainly so much more well-equipped to handle anything that's coming my way. But we should be working harder on ourselves than we do on the business, because we're the ones running and operating the business. So if we're not at our full capacity then that could really impact the business.

Jen Kelly:

I'm a firm believer that your business is a reflection of you and wherever you are in your kind of evolution and journey and all of your relationship dynamics, all of your confidence, it's like it just becomes a reflection of you and how you build the company. A lot of your indigenous heritage is rooted in the values of your company. Was that something that was like of high value and importance to you before starting Cheekbone Beauty? Or was that really brought on by kind of the vision and mission?

Jenn Harper:

I would say there's been an evolution of me understanding my Indigenous roots. I grew up with my mother, who's not Indigenous, and so I didn't really have a strong connection to my culture or my community for the majority of my life. So it wasn't until my mid-30s that I started to connect, even with my family. As a young person, you know, my dad had his own struggles and at 19, I just decided to cut all ties with him. I thought I'm an adult now, I don't need to have this relationship. I'm an adult now I don't need to have this relationship. And also me understanding one the entire systematic abuse through residential school system and the systematic abuse that then that left on my culture, which included my family, which included my father. So now I recognize with really clear eyes that my father was a product of the system that he was raised in, and so I now look at that completely different and have so much gratitude for the love that I got from both of my parents, despite what my dad had to live through and go through and experience, and recognizing and learning about this term called generational or transgenerational trauma, which was impacted greatly by the residential school system which my grandmother survived. It was passed on to my father and then ultimately passed on to me and my siblings. And so when you have that information and you know, when we know better, we can do better. And so just I then decided, okay, no, this is a big part of who I am.

Jenn Harper:

For me, I had struggled with addiction for many years and one of the ways that I've been able to manage recovery was just eliminating this whole idea of shame, and so now I feel very proud of who I am and where I've come from. But it's so true that how we've been able to take this company and incorporate a lot of those teachings into the kind of business I want to build. And, of course, I want the core values to be surrounded by the things that are really important, and these were being pulled from my Anishinaabe roots. So we used what is called our seven grandfather teachings to build our core values at Cheekbone Beauty, which are values and principles. One is just based on love, humility, bravery.

Jenn Harper:

Another teaching is the seven generations teaching, which is really about environmental impact and what we do today and how it impacts not only the next generation but the next seven generations Learning that the idea of success within our Indigenous communities is more about what you're doing to give back to community versus what you're attaining for yourself. So they're really in opposition of like this Western idea of success really in opposition of like this Western idea of success. For us at Cheekbone Beauty, it was definitely a way to set ourselves as a unique position in the marketplace as well. There's not a lot of Indigenous-led or run beauty companies and at the time when we started there, there was very, very little. There was none working with Sephora, and so we wanted to uniquely position ourselves and by adding our teachings and our culture into building the business and brand is really what sets us apart.

Jen Kelly:

Jen, how did you actually apply the teachings practically through the business? I would love for many more companies to kind of be able to integrate and move in this direction. How should leaders actually think about taking this concept and like what would be some real life examples that you guys did?

Jenn Harper:

So at first it was really challenging in the sense that. Is this even possible? It's like you're like rebuilding a whole new business model, if you will, and one. There's expense challenges. We all know, like capital is a big struggle for entrepreneurs, always Then having to find investors that believed in building the kind of business and the kind of business where we became a B Corp certified company in 2021. So this is after we had started.

Jenn Harper:

However, finding the B Corp community really aligned with the value system that we were trying to achieve, because it's this idea that we're putting people and the planet before profits, which, in most cases we're in business, are we, you know, filling stakeholder pockets versus actually taking care of those other things, which feel far more important, but unfortunately, that's not how it really works in the business world, and so one finding an investor that believed in that.

Jenn Harper:

That was key, right, because then now, when you're at a board meeting and you're making a decision and moving all of our box production out of China and we want it all done in Canada and there's a cost to that right.

Jenn Harper:

However, being closer to home is just helping us manage and ensure a very ethical supply chain, and that's really important to us as a business and as a brand. And two, a lot of organizations now have different certifications that really speak to their environmental impact, and so working with the local suppliers really helped us be able to manage that better and make sure that we're doing the things that we say we're doing. These are tough decisions, they're expensive in many cases, and it creates a lot of conversation around those board meetings. In that boardroom I feel like sometimes we're just driving and going down these roads trying to prove that if small business can do it, large business can do it too, and they probably have the ability to do it far better than we do because of their size. Right Volume is a big deal in a lot of these spaces when it comes to manufacturing.

Jen Kelly:

Yeah, and I guess you know there's. There's the aspiration, there's the integration of putting these systems and practices into the business, and then there's holding the line right and being a leader. What have been the headwinds that have challenged you and how have you held your center?

Jenn Harper:

I think, market changes. They've been really challenging, and that is, I think, just access to the customer. You know, we grew on social media and we grew during that time of, like, rapid social media growth and e-commerce growth and being in that space and everything has dramatically changed since we launched in that world. So that has been tough, even just like, when I think about it, all the things in the side, like figuring out how to we make our formulations, which a lot of makeup companies are just relying on partners. They do what is called white label or private label. So those formulations are one and done. But I also think that uniquely positions us to really see things differently in the marketplace. You know there's a lot of passion behind startups and small teams. That doesn't exist in a large organization, right?

Jen Kelly:

Absolutely. And as you've thought about your growth as an entrepreneur, where have you seen the biggest evolution in yourself?

Jenn Harper:

I've changed so much from the beginning. I remember just like in the early days you're so idealistic, like you're just such a dreamer, yeah, and I still feel like that's there, but with maturity now, right like not not just talking about this dream or fantasy, but really understanding it's all about execution and strategy and planning and organization, and I feel I've learned so much about myself along this path, which is something I feel unexpected too. Like you don't think about that while you have this early idea or set off on this venture to start something, I've just learned a lot about myself. I really know my weaknesses, but I love sharing that with new entrepreneurs just because I think it's so important to recognize like it doesn't mean you have to know all those things in order to actually make something work and make it successful, which is really key.

Jen Kelly:

Well, and I think this is why your story will inspire so many people who are kind of on the cusp or in the journey. You know, as I was kind of doing a bit of research for our show, I was surprised to learn that you had been on Dragon's Den, and even since that time now your products are in Sephora. Like, what did you learn through that chapter?

Jenn Harper:

I never thought that I would have the courage to be able to go like pitch my business, because that was the first time I would actually pitch the business in the sense where I was doing it. I think in the traditional sense of a pitch right Like this is your got two minutes that you have. So that really helped me focus on what the business is and who it had to be and all of those things, even though it's dramatically developed and evolved since then. Like, the things that have made me the most uncomfortable are really the really big growth moments. For me personally and I think for the business too, like that was a dramatic, pivotal moment for the brand. Tons of it was a great marketing opportunity for sure. I encourage anyone who, especially in CPG or product-based business, if you have something like, get on a platform like that, because it's going to be a really big moment for for the business. Yeah.

Jen Kelly:

I've been thinking a lot about exploring the difference between confidence and worthiness. We can be confident in our skills, but worthiness especially as it relates to receiving help, receiving money like worthiness is a whole different category in the subconscious. Have you experienced the difference between having to work on confidence and worthiness in your own entrepreneurial journey?

Jenn Harper:

I feel really fortunate because of my sobriety journey yeah, like it really has set me up for success in business One, because I feel like I accomplished an absolute miracle. Right when you struggle with addiction and you overcome that, it feels like a mountain-like obstacle and overcoming it feels really powerful and really special, and so I feel very blessed because that's given me a lot of real evidence. So what we need in life sometimes as people, is we always need evidence that something is possible, and when you create your own, it's like faith, it's like an incentive. I have faith in myself because I've already accomplished something so big. Do you know what I mean?

Jen Kelly:

Yeah, yeah, yeah.

Jenn Harper:

And then I also, I have a very personal relationship with the creator of the universe because of my sobriety journey and for me I feel worthy because of that and I'm just so connected and I obviously I I've shared this often, but when I'm in nature, especially like seeing creation is evidence of me, of the creator of the universe, and that I have this, I'm alive Like I'm in, I exist, and I'm grateful because I'm meant to be here. I probably struggle more with like the confidence thing, because sometimes I feel like I'm being fake confident, Right Cause I'm like oh how so?

Jen Kelly:

Cause I don't, I feel like I don't have a lot of skills, skills defined as, like I, was formally trained in these things, exactly so because of that I feel like I've always struggled with the confidence side of things.

Jenn Harper:

And then so many of wonderful friends and obviously I think from my female circle are like look at what you've done in your life. Despite not having the formal training of all the, you have the training, like so many friends that carry MBAs are like you built the business. We're just reading case studies to get a piece of paper that say we have an MBA, so like, but you've done it.

Jen Kelly:

Having the conviction that this is bigger than you, the mission. That was the energy that you were like pushing out there. And then, when you talk about the confidence, it's like you know you can have the vision for the mission and you could feel terrified that you don't know how to do blank, blank, blank, cause the confidence is all about yourself. The mission is like it's outside of you. Right, it's the service, it's the bigger piece, and I think that's the energy, at least for me. That's the energy that's propelling me forward.

Jenn Harper:

And it's the thing you almost can't control. It's really interesting. There were times when I would meet people in the early days and you could tell they they just they weren't getting what we were, what I say we, but it was just me. They weren't getting it. But then I would meet the people that felt the energy of it Right and we're like that was like so, like revitalizing, when you would have those moments where and that and it would help me not give up literally.

Jen Kelly:

Um, I want to formally just thank you so much for being here. I was, uh, watching you from afar like social media, the brand probably six months before I reached out to you to be on the show, and I'm just so impressed by everything. So thank you so much.

Jenn Harper:

Thank you so much. That means so much.

Jen Kelly:

Yeah, yeah, I think people are really going to enjoy everything you shared. So thank you, jen, for being here today.

Jenn Harper:

Thanks for having me.

Jen Kelly:

Thank you for joining us. Don't forget to follow us on Instagram and LinkedIn, where we transform the wisdom from our podcast into practical tips, tools and takeaways for your leadership journey. Find us at gritgracepodcast. See you next week.