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Success Without an Asterisk

Since my book Backroads Boss Lady was published earlier this spring, I get asked a lot of questions. Some of them—mostly about how I grew Cheekys, a multi-million-dollar rural apparel and accessories business from scratch—are easy to answer. The personal ones are harder. Recently, I was asked how I knew that I had become successful. I answered: when I could stop keeping secrets.

I didn’t go to some fancy business school. Heck, I don’t even have a college degree. I dropped out of high school in Midland, TX, senior year. For a long time, I didn’t want anyone to know about my lack of formal education. I consider myself a lifelong learner, and thanks to the internet, it’s easy to access free information to help you learn all you need to in order to achieve your goals. But mostly, I didn’t want to be the girl people said had done pretty well in business—for a high school dropout.

Backroads Boss Lady by Jessi Roberts

(Image credit: Jessi Roberts)

Growing up, my family and I lived in pretty extreme poverty at times. We didn’t always have a safe place to sleep at night, and my mom’s addiction and poor relationship choices meant that I was often in charge of caring for myself and my siblings. When I moved out as a teen, I didn’t understand what a stable family looked like. Unfortunately, that led me to pick some not-very-nice men early on in my life. I didn’t understand that I was worth more than the way I was allowing myself to be treated. When I reflect now on those memories, it’s still hard not to wince inside. I don’t want to be defined as the woman who found great success is business—for a survivor of domestic abuse, homelessness, and childhood trauma. 

When Inc. Magazine profiled me in 2017 as the former Outback waitress who built a major retail brand, my life got pretty crazy—in a good way. The folks at Inc. introduced me to my agent, and I ended up with a book deal with a big New York City publishing house. As part of the process, I interviewed several so-called “ghost writers” and one, Bret Witter, really impressed me. It’s important to me to be transparent about this process because I don’t want any women (or men) reading this to think, “Look at Jessi, she can really do it all: raise four kids and grow a successful business, and have time to write a book.” That’s just not how it works. I told Bret, and my publisher, he needed to be recognized as my co-writer on the cover of the book. 

That commitment to honesty came back to bite me when Bret leveled with me about my openness to sharing my story in the book. I thought Backroads Boss Lady was going to be a business book aimed at helping mom-and-pops in small town America. Instead, it became a deeply personal, inspirational memoir about the grit, heart, and hustle it took to build Cheekys and the life and family I’m so proud of. Bret said if he was going to be listed as my co-author, I had to do the work of digging deep and coming clean about all the experiences that make me who I am today. 

That was scary as hell. 

I didn’t want to revisit a lot of the memories I write about in the book. There was stuff I hadn’t even shared with my husband, Justin, yet. But mostly, I didn’t want to be successful for a girl “like that,” or for a girl “who’d gone through that.” I didn’t want to be considered successful, but with an asterisk attached to my name. 

Through my conversations with Bret, I shared my true story in the book. I learned that true success comes when you are comfortable in your own skin, not when you hit $20 million in sales. When you have the courage to admit that you actually only sold 200 sherpas instead of the 2,000 you’d forecasted, or that a design you thought was hilarious totally flopped. When you decide it’s worth it to come clean about your past in order to help the next up-and-coming unlikely entrepreneur who might learn from your experience or at least feel a bit less alone in their journey. That’s what motivates me today, asterisk be damned. I can talk about the secrets of wholesaling or leveraging social media, or how Cheekys is poised to build a distribution center in Australia in the next year, but in the end, none of it matters unless I’m real about who I am and my journey. 

These days, when I speak to audiences of thousands, I try to leave a few key takeaways for the audience. Here goes:

1. Embrace the journey. Building a business is not unlike parenting. Sometimes we are so excited for the toddler to get potty-trained we miss all the hilarious antics of the moment. Your business might be a toddler, and that’s a great phase to be in, so don’t get caught up in future milestones. 

2. Be authentic. Do the work to discover who you are and communicate that through your brand to your customers. It will set you apart from the pack and you will feel a heck of a lot better inside, too. 

3. Be brave. You were put on this earth for a reason, so don’t run from it. Lean into it, and the rewards will astound you.