Overdraft: How One Founder Is Changing Lives—Including Her Own—Through a $500 Start-up

Illustrated portrait of Cheekbone Beauty founder Jenn Harper

In this series, I speak with people who know what desperate feels like. While now blooming into success, these founders share with me their deeply personal financial struggles and lessons learned on their way back to black.


This is the story of how Jenn Harper’s beauty business—an idea that once came to her in a dream—saved her life.

For years, she battled addiction and was once on the brink of losing everything. When she began to rebuild her life, she redirected her energy toward creating Cheekbone Beauty, a sustainable cosmetics brand that sells products like lip gloss and gives back to youth in her Indigenous community. That community became the impetus for getting—and staying—well.

Today, four years after she woke up from a dream that inspired her to build a beauty business, Jenn is quitting her day job and focusing on Cheekbone full time. The move will shake her financial stability just as her kids are preparing to attend college. But she feels optimistic as Cheekbone levels up with funding and prepares for a new product launch in late 2019.

Here, Jenn explains how she overcame alcoholism, generational trauma, and the challenges of starting her business—with just $500.

In Jenn’s words:

“For about eight years, I had a battle with alcoholism. My marriage was falling apart, and the alcoholism grew and developed and filled out until it got really, really scary. I almost lost everything, including my kids. It was awful. Horrific.

I’ve always wanted to get well. In 2014, I read that alcoholism is a pathway and that you literally cannot just give it up—you need to fill it with something else. So, I filled it with recreating my entire life. People say, ‘You’re not even the same person. You literally transformed yourself.’ And that’s what it took. It’s like building a house. I had to build a new foundation and reset everything. My new pathway is Cheekbone Beauty. I’m an addict. I have an addictive personality, and that’s why I can do this business—it’s an addiction.

We all have this ability to really change who we are.

It took me a long time to admit I was an alcoholic, because I never wanted to set that stereotype of our people. But my father is an alcoholic and my grandmother was, too—it’s called generational trauma. We have to just change it. We have to stop it. I don’t want this life for my kids. All of us as Indigenous people right now are really working hard to change that narrative of the past. I am so proud to call myself a recovered alcoholic. We all have this ability to really change who we are.

I got sober in 2014. My husband and I are still together—almost 20 years—because I worked so hard on it. Then in January 2015, I had this dream about little native girls covered in lip gloss. I woke up, and I was just like, ‘This is it. I’m going to make lip gloss, sell it, and start a foundation in my grandmother’s name.’ She was a residential school survivor.

An advertisement to read Overdraft: a series of stories about deeply personal stories of financial struggle.

During those years that I was building Cheekbone and getting well, I was learning about the beauty industry while also studying my culture and learning everything I could about it. I feel like I have to be a role model for Indigenous youth. I have to show them that these systems and governments we live under have failed Indigenous people in so many ways. Let’s stop relying on them, let’s build our own economic systems that are beneficial to us, our communities, and our families, and ultimately the world.

I’m not making any money yet, but I’ve never felt more rich in my entire life.

I’ve always had a full-time job, so I was able to fund this myself. I know lots of people, especially from Indigenous communities, that don’t have that kind of funding. I never understood what it all meant: seed round, seed funding, next round of funding. Now I get it. But I read 100 books about building businesses between 2015 and 2016. I was a massive sponge over those two years.

I’ve been really successful in my career, and I’ve had great jobs, but I believe that you have to give something up in order for something great to be born. You’re going to make a sacrifice. I didn’t go on a vacation for two years with my family. And there were times when it was tight. People think there’s financial gain. I’m not making any money yet, but I’ve never felt more rich in my entire life.

I actually get to quit my full-time job, which is the most exciting news ever. Now, my hours will go directly to my business instead of somebody else’s. But I’m going to cut myself down to a fraction of the income that I’m used to, so there’s a big fear. Then, I’m managing the fear of my husband, as well—we have a kid who’s college-bound in a year and then another one three years after that.

I’ve been really lucky because Cheekbone Beauty has been successful so far—successful in terms of what I’ve been able to accomplish in such a short period of time. I started this with $500 and, in 2019, we hope to end the year at over $300,000. I started a business that was all about giving back. I’ve given over $5,000 to the First Nations Child and Family Caring Society. That was the main reason I did this. Ultimately, if the effort behind Cheekbone Beauty failed, at least I did what I said I was going to do.”

Illustration by Germán González An advertisement to read Overdraft: a series of stories about deeply personal stories of financial struggle.