Photo of a woman with dark hair wearing fuchsia lipstick, a necklace with turquoise coloured stones, and a dark blue blouse

Women Entrepreneur Icons: Jenn Harper


“The whole reason our brand exists is to help Indigenous youth see their value in the world.”

In partnership with the Coca-Cola Foundation’s 10,000 Women Entrepreneurs Initiative, Startup Canada is celebrating and spotlighting leading Canadian Women Entrepreneurs. Startup Canada was pleased to sit down with Jenn Harper, Founder & CEO of Cheekbone Beauty to learn about her journey and the impact of their work.  

Jenn was born in Thunder Bay, Ontario and raised in the Niagara Region where she developed a passion for cosmetics. She founded Cheekbone Beauty in 2016 when she noticed a gap in available cosmetics brands. She wanted a brand that was made in Canada, that was never tested on animals, and that gave back to the First Nations community—so she created it herself. Jenn strives to educate Canadians about the Residential School System and the effects it’s had through decades of generational trauma. 

She was awarded the Social Enterprise Award at the 17th Annual Women in Business Awards by the Women in Niagara (WIN) Council and the Greater Niagara Chamber of Commerce (GNCC). In 2018, Jenn was invited to sit at the table with Prime Minister Trudeau and discuss the strategy for the Women Entrepreneurs Fund (WEF). Most recently, Jenn faced the Dragons on CBC’s Dragons Den and won Social Enterprise of the Year at the 2019 Startup Canada Awards.

SC: In one sentence, what does being an entrepreneur mean to you?

JH: Creating your life around work that you’re passionate about.

SC: Can you tell us about your entrepreneurial ventures and what role they play in your life?

JH: Cheekbone Beauty Cosmetics Inc is the only venture I’ve had the opportunity to be in—and it’s been a life-changing experience. I didn’t know that it was possible—and I feel extremely grateful that I get to call this a job. As hard as it is, it doesn’t feel like work because I’m so passionate about what we’re doing.

SC: What motivated or propelled you to become an entrepreneur?

JH: Journalists have called me an ‘accidental entrepreneur’ and I really feel like that is the category I fall into. I never set out to do this on purpose.

I had a dream, and from that dream, I decided that this was what I was going to do. I’m going to make lip gloss. And so began the work and the journey of self-discovery and learning.

That was in 2015, and I worked my full-time job up until August 2019. We didn’t have a product to take to market until the end of 2016, so it’s been quite a process ever since that dream.

SC: What inspires you to keep going?

JH: Number one is a conversation I had with my brother. Unfortunately, he took his own life in 2016 just before our launch. As tragic as that situation and that pain has been for me—and will always be—I think I’ve learned to live with it differently and cope with it better. He talked about the hope and help that our Indigenous youth need. 

With everything that he knew about the business, he said, “this is going to be great Jenn,” and, “our kids need this.” It’s his words—on the days when I think, “why am I doing this? I want to give up,”—that keep me going. That is the driving force; this hope that I know Indigenous kids need.

That whole concept that you can make a living and do work that you’re really passionate about is what has kept me going—and the reason our brand exists is to help Indigenous youth see their value in the world.

SC: What is the next mountain you are climbing and what is left undone? 

JH: The next mountain—what we’re calling ‘Cheekbone 2.0’—is actually making products that are more sustainable. As a brand, we want to make the biggest impact possible on Indigenous youth, while leaving the smallest impact on the planet. We’ve been doing a great job at that first part of our business, but the second part is where we are right now. 

When you’re making packaging that’s biodegradable and compostable; and trying to sustainably source raw ingredients, there’s so much education involved on our part as a brand. Then actually putting that together has been the biggest challenge. 

It’s coming together. We’re excited to hopefully have a lipstick that we’re calling the most sustainable lipstick in the world. The packaging will be compostable and not leave any impact on the planet. The raw ingredients themselves will not affect the ecosystems or waterways that they fall into. The Buy Good Feel Good Expo that happens in Toronto from March 27–29, is our public launch of that product.

SC: What has been your biggest learning along the way?

JH: I’ve learned so much, but I guess the biggest learning—in business or life—is that you’ll never know everything and that everything is a learning opportunity. You should always be open to thinking about things differently.

SC: Have you identified or confronted any systemic barriers through your journey? If so, how have you persevered through them?

JH: I don’t know, because I personally probably wouldn’t focus on it, even if I did. I feel like the right people have come around, or the right organizations or the right supports have been there when we needed them.

Of course, there are down days when you’re an entrepreneur. I think the moment you figure that out, like—whoo! You’re on top of the world and then you’re at the bottom of a pit—and that’s the ride; that’s the journey. There is no end destination.

I’m learning that about our sustainability mission, too. It’s all a journey. I don’t know if this comes with maturity, but I’ve just learned to enjoy it as it’s going. So if even if barriers come along, I’m just choosing not to pay attention to them.

SC: That’s a great attitude. What advice do you have for those just beginning to embark on their entrepreneurial journey?

JH: Full-on consistency—and it doesn’t have to be massive movements or actions. Every day, do something that’s going to move you toward the goal of the business that you’re trying to create. 

And don’t give up. As hard as it is, I think the successful businesses—the ones that work—that we see globally that are really successful, it’s been about consistency and believing in the thing that you’re trying to build.

SC: Where can people go to learn more about your journey and organization?

JH: Our website—that’s where everything lives.

SC: What is your big vision for Canada and the World over the next 20 years?

JH: To truly embrace each other. Kindness is so powerful, and that golden rule—can you imagine if we all actually applied it?

SC: What do you think today’s entrepreneurs should be focused on for a better, brighter future?

JH: Figuring out how to look at some of the big environmental issues that we’re facing and doing something to minimize the impact on our planet.

Have you woken up from any powerful, entrepreneurial dreams lately? Join the Startup Canada Women Entrepreneurs Network to gain access to resources, community events, and start your own entrepreneurial journey!

Micah Rakoff Bellman
Micah Rakoff Bellman

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