“Rags to riches” may be a cliché, but for Jessi Roberts, it rings true.
The founder and CEO of Cheekys has come a long way from a tough childhood in Texas — where she and her mother, an exotic dancer, sometimes lived in abandoned homes — to head of a multi-million dollar fashion brand.
Roberts, a mother of four, had everything against her when she launched Cheekys in 2011 with six purses and a tanning bed — funded by cashing out her $7,000 life savings. But, through dedication, savvy and hard work, Roberts managed to turn that inauspicious beginning into a successful online clothing and accessories company that is carried in over 4,500 stores. Her 1.5 million die-hard fans, known as “Cheekys Chicks,” avidly follow her progress on social media.
Throughout her rise, Roberts has made a point of giving back to her community, New Plymouth, and mentoring the next generation of women business owners, particularly those in rural areas. Her track record of professional success and service earned her a place among the Idaho Business Review’s 2019 Women of the Year honorees.
Now Roberts is telling her story in a new book, “Backroads Boss Lady: Happiness Ain’t a Side Hustle – Straight Talk on Living the Life You Deserve,” co-authored by serial New York Times bestselling author Bret Witter.
Roberts recently chatted with the IBR about her upcoming book tour, the state of rural business and how an unsolicited comment to Inc. Magazine can change your life.
Your book was just released. How did it come about?
“Backroads Boss Lady: Happiness Ain’t a Side Hustle – Straight Talk on Living the Life You Deserve” was published on March 5, but the process has taken about two years. It started when I reached out to the social media editor at Inc. Magazine to point out that, while I liked the magazine, I felt like a lot of folks in my world – rural mom-and-pops – would never read it because the content doesn’t really reflect their lives or businesses.
My note somehow made it to the desk of the VP, and they ended up doing a profile of me in 2017 titled, “How this Former Outback Steakhouse Waitress Built a $2.8 Million Retail Brand.” That led to the reporter connecting me with my book agent, who was a longtime friend of hers. I talked to several publishing houses that were interested, but ended up going with Grand Central in New York City.
What was the most surprising part of the process of working on the book?
How personal it became. I started out thinking I was writing a business book aimed at rural mom-and-pops. I wanted to write the book I wish I’d had when I started Cheekys in 2011. But as you see quickly when you read the book, it’s equal parts business how-to and a very personal memoir. It was a lot harder than I thought it would be to revisit my past, especially when I recorded the audio book version.
I think the other thing that surprised me is this beautiful friendship that came out of working with Bret Witter, my co-author. It was super important to me that he be listed as a co-author because I don’t want women out there reading it to think, “Wow, look at Jessi, she has time to run this successful business, raise four kids, and write a book.” I try to always be real, and so much of what you see in publishing isn’t.
What do you hope people will take away from your story?
The importance of authenticity. And that I’m not all that different from anyone else. We should all stop running this imaginary race against one another and our competitors. Once I stopped comparing myself to others, that’s when my business and life really began to flourish.
You are embarking on a book tour, which will connect you to many readers in person. What has it been like for you to meet fans?
So great! I have met many of them over social media already, so it’s fun to meet in real life too. Cheekys engages with 2 million followers a week, and our “superfans” are definitely some of my favorite chicks. It’s also been great to meet and connect with unlikely readers, including men and women who have never even heard of Cheekys. I’m happy that my story resonates with a wider audience than just Cheekys shoppers or boutique owners.
I also think rural, regular people don’t often see their lives reflected in books or in the media. I want to show the world that rural stories deserve to be told and that rural girls can (hopefully) write bestsellers too.
Your company has grown and developed a lot over the past few years. Where would you like to be in five or 10 years?
I’ve really stopped trying to plan all of that too much because I feel like it takes me away from enjoying where my business is right now. It’s kind of like raising a kid – too often we are focused on getting them to walk or into school or graduated and we miss all those wonderful moments along the way.
Cheekys operates a bit like an iceberg in that we are massive and could probably take out the Titanic, but we’re also slow to make any sudden moves. I think we’ll continue to grow. We’re looking at opening a distribution center in Australia, one of our fastest-growing markets, and we continue to look at how we can improve downtown New Plymouth.
You also have a big footprint in New Plymouth. Talk about some of your hopes for the community.
New Plymouth is a great town in many ways. It’s absolutely beautiful here, for one. That said, it can be hard to find employees willing to commute the opposite direction from Boise to work with us.
As I discuss in the book, we haven’t always been welcomed with open arms here because of my custody battle and because we were outsiders in some ways. I’ve lived in Idaho for 20 years and my husband is a farm boy from Homedale, but that’s not always enough to make it into the “in-crowd,” I’ve found.
You are a great advocate for rural businesses and women-owned businesses. Talk about the value of these types of businesses and why you felt the need to step up and advocate for them.
I think rural people, and rural women especially, know a lot about what it takes to really hustle. You want something done? Ask someone who grew up on a farm or ranch.
We hear a lot about the lack of economic opportunity and jobs in rural America, but less about the potential for entrepreneurship to thrive here. I am very thankful to Idaho for creating conditions that helped my business thrive. The state has been really helpful, as well as the local Snake River Economic Development Authority. Sure, there’s been a few surprises, like the 1800s-era brick in our buildings disintegrating and the floor literally falling out from underneath us. The town has not being able to accommodate our internet utility needs, but we’ve worked through most of that. Anytime we make infrastructure or utility updates, we’re glad it’s helping us, as well as hopefully making it easier for the next person who comes along.
What advice would you have for other business owners?
Find joy in the journey. When I first started my business, I didn’t have a lot of joy. I was trying to feed four babies. And sometimes I really wish I could go back and tell myself to find some joy during those early years. My brand would have grown so much faster if I had, and I would have had a lot more fun. It’s like raising your children: you have to pause and enjoy all those little moments on the journey because that’s what matters and makes life fun.
You are an IBR Women of the Year honoree. What does the award mean to you?
Oh man, it means so much to be among the incredible women in this group! I’ve made some great friendships out of it, and I’m so happy that Sen. Buckner-Webb received the Woman of Year honor.
Honestly, I felt like I’d already won the award when I read the letters of recommendation from my employees. To me, the best part of owning a business is being able to hire and financially support other hard-working families.
I talk in the book about how the folks that run TED Talks would never accept one from someone like me – a rural high school dropout with a difficult past. Writing the book and seeing the reception to it so far has helped me get over some of that. I am feeling more like, “Hey, you know what, I am enough, and I have worked hard and deserve this.”
The 2019 Women of the Year theme is “What unites us?” You can interpret the question to mean “as honorees, as women or as humans.” What’s your answer?
I believe we all have more in common than not, and that when we take the risk of showing people who we really are, only good can come from that.
It’s hard to build authentic relationships – with customers, employees, heck, even your spouse and kids at times – but it’s what makes life worth living. I am who I am, and I hope by sharing my story, other people will feel freer to be who they are and feel proud of that.