Jenn Harper

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We have a ton of readers who hope to start their own business one day. Tell me about Cheekbone – how did you get the inspiration (and motivation) to start your own business?

My pathway to owning my own business is different from your average entrepreneur – I’ve always worked for other people in sales, and I’m definitely not a ‘serial entrepreneur’ type.

But I also had a huge desire, deep in my heart, to help my people. I just didn’t know how to do that.

Then one night I had a dream about two indigenous girls covered in lip gloss – I woke up and just knew I had to create a cosmetics company.

I read 100 books on business and about my culture that year, including the entire Truth and Reconciliation Report. I researched the Canadian cosmetics landscape, and I spent a lot of time considering how I could make the industry more compassionate.

Cosmetics are incredibly wasteful, so moving towards a zero-waste operation was central to Cheekbone’s business from the get-go. We should be completely waste-free by 2023.

I also wanted the company to give back to indigenous youth – I really believe in the power of education, so we give 10% of our profits from all purchases to Shannen’s Dream in support of education equity for indigenous youth. Ultimately, I want to build out our own scholarships.

I am so drawn to your mission of marrying social responsibility to the business – why is that so important to you, and how have potential investors or partners reacted to that?

So I’d been doing Cheekbone completely on my own for the past three and a half years, entirely self-funding the business, and I was always committed to the social vision of the company. I needed to truly believe that the market would want this concept before I approached investors.

Since things have taken off, I’m now working with an investor who really believes in me and that compassionate vision. I couldn’t grow Cheekbone to where I would like it to be without outside capital.

We’re also working with the first Canadian indigenous venture capital firm, which is amazing. They’re helping us get the next stage, but neither investor has asked for equity – I still have 100% ownership of Cheekbone.

Most people are familiar with the concept of an entrepreneur as a wealthy, old-ish, white dude. Yet you’ve had great success, as an indigenous woman, and as a mother of young children, creating a business and giving back to your community at the same time. Has being an indigenous woman, and a mother affected your business in a positive (or negative) way?

It is sometimes heartbreaking what indigenous women are up against – people miss the potential of indigenous people in business, and especially indigenous women, and we have to work harder because of that.

But I really do choose to focus on the positive – whether it’s the emails from customers after purchases or after speaking events, I know the mission of Cheekbone is resonating. Its not just indigenous people, but many non-indigenous allies have supported Cheekbone, whether through an introduction, or just offering to help.

So many terrible things have happened to indigenous people in the past. But especially as a mother, I’m really interested in building a better future for our youth.

You’ve spoken openly about intergenerational trauma from residential schools, and about your own family’s struggles. I think that’s so important, but also extremely difficult. How has starting that conversation tied into Cheekbone’s success?

It’s an overused word, but it’s all about ‘authenticity’.

This business only exists because of my sobriety, and it’s been so healing to tell my story about recovering from alcoholism as I build it. I can’t even believe I’m telling people that I’m a recovering alcoholic.

It’s also been so important for me to realize and to share with others how closely tied my alcoholism is to intergenerational trauma. My people survived genocide. But for us now, our generation’s challenge, across Turtle Island, is not just to survive but actually thrive.

Overcoming addiction, and giving up my alcoholism, felt like losing a limb, but now that I’ve overcome that, building up this business seems so possible.

You’re a mother, a wife, an entrepreneur, and you speak across the country about your journey. What have you learned about balancing work and life in the process?

Women need to know no such thing as ‘balance’ exists in entrepreneurship, unless you have enough money to afford help.

I honestly don’t know why this succeeded versus someone else doing this, but it has a lot to do that with me having confidence in my mission – I don’t think anyone who has succeeded as an entrepreneur has been in it for financial gain originally.

Your background is in sales, but now you have a hand in every aspect of Cheekbone – how has that professional transition worked and what have you learned?

It’s been a process. I’ve taken courses here and there to learn skills, but it’s also so important to know when to get outside help when you need it.

When they say, “hire your weakness”, it’s so true. I wasted so much time trying to teach myself accounting before I just hired an accountant. At the end of the day, you’re only one person.

On the other hand, sales was really helpful in the marketing component of the business. I started teaching myself about social media back when I was in sales, because I knew the power of it and how it would change the digital landscape. That’s been really helpful for Cheekbone.

What are the major challenges you’ve experienced in the Canadian cosmetics (or consumer goods) industry?

As a Canadian entrepreneur, you have to realize that Canada is a really, really small market. Don’t be afraid to go global right away, and don’t be afraid to export.

We actually have favorable taxes for shipping merchandise to the States, which is something any entrepreneur should really take advantage of – there are 300 million potential customers.

What’s next for you and for Cheekbone Beauty?

I recently quit my full time job, which is a huge step. And I recently appeared on Dragon’s Den, which will air this Thursday, September 26th, at 9:00PM EST on CBC and CBC Gem.

We’re a digitally native company, so we’re constantly looking to innovate and make our online shopping experience smoother and more interactive.