Cheekys Founder & CEO Jessi Roberts/h4>
Story Caitlin Copple Masingill Photos Kimberlee Miller

Jessi Roberts doesn’t have the luxury of failure.

She started Cheekys, the New Plymouth-based Western lifestyle ecommerce, retail, and wholesale company, in 2011 as a hard-working mom with $7,000 in life savings and a prayer. Her family of six and husband who had been injured on the job needed her support – and fast.

[blockquote author=”Jessi”]It was time to hustle. I needed to make some money.[/blockquote]

A former Outback waitress and used-car saleswoman, Jessi was no stranger to hard work, and it shows. This year, Cheekys became one of 14 Idaho companies (and the only one led by a woman) to make the Inc. Magazine 500 list for rapid growth. Cheekys products are available in over 3,500 boutiques, including several in Idaho, as well as online at

Jessi’s first book, Backroads Boss Lady: Happiness Ain’t a Side Hustle, comes out March 5 with a major New York publisher. The hybrid memoir and small business book has been endorsed by the likes of Lee Woodruff and The Myth of the Nice Girl author Fran Hauser, and led to interviews in Real Simple Magazine, Forbes, and Marketplace.

Closer to home, the Idaho Business Review named Jessi among 2019’s Idaho Women of the Year – she figures she’ll have to buy a dress for the gala. The night before, on March 5, she will hold her first reading Boise’s Barnes & Noble.

Despite the success, Jessi is working harder than ever from her bustling office in Downtown New Plymouth, population 1,538. She goes live on Facebook each day, reaching more than 2 million women a week through the platform, personally mentoring hundreds of aspiring or novice boutique owners.

It’s still all about Cheekys sales, even with more than $500,000 coming in each month, Jessi says. At the big fashion shows she attends several times a year, Jessi sets up her own booth and merchandise and then helps take it all down, sweating beside her staff and husband. She buys all the samples after a show, figuring if they don’t sell through Cheekys, she’ll sell them at a yard sale if she has to. That ethos, as well as a deep understanding of her customer, is what drives sales.

“Jessi not only created a million-dollar company, but she created, a die-hard, sisterhood of chicks that continues to grow,” said Erika Mata, Cheekys’ sales manager.

Jessi thrives on the pace and finds inspiration in the community she’s created of fellow rural entrepreneurs. Business ownership has meant more time with her family and a better future for her kids, who often work alongside their mom, dad, and grandpa in one of the many buildings Jessi has purchased in Downtown New Plymouth. Jessi’s own childhood, much of it detailed in her book, was a struggle, and home was rarely a safe place to be. She’s determined not to let her past define her, but also not to run away from her roots, which is why she’s relentlessly authentic in telling her story.

“My dream life is really to have an in-ground pool,” she laughs. “I already have an above-ground pool. I want to make a change in my community, I want my little girl to have a better place to grow up than I did.”