Jessi Roberts

Cheekys founder and Resident Boss Lady Jessi Roberts, a mother of four, had everything working against her– including an abusive past, poverty, self-doubt, and a community resistant to change – when she used her life savings of $7,000 to build a small store on Main Street in New Plymouth, a fading 1,536-person community in rural Idaho. Today, Cheekys employs 30 (mostly) local women in a successful e-commerce and wholesale manufacturing operation.

With millions in annual sales and a national reach of more than 2 million a week on social media, Cheekys is a top five global boutique with its products carried in more than 3,500 retail locations. Jessi was named to Idaho Business Review’s Women of the Year in 2019, and Cheekys was named one of the fastest growing companies in America by Inc. magazine in 2018. Her first book, Backroads Boss Lady: Happiness Ain’t a Side Hustle - Straight Talk on Creating the Life You Deserve, was published March 5, 2019, by Grand Central.