Jessi Roberts turned a small-town clothing store into a cheeky online success story

A longhorn skull studded with Swarovski crystals and adorned with leather feathers hangs on the wall behind Jessi Roberts’ desk, an eye-catching gift made by a friend.

The wall itself is covered with corrugated metal that came from her barn, and another wall features a screen door turned sideways to create a textured frame for a shelf of family photos. A huge vintage raindrop chandelier brightens the room that brims with objects of different shades of teal. Roberts loves those blue-and-green hues, and every item in her office seems to have a sentimental story.

Welcome to the Boss Lady’s new lair — a room at the back of a renovated dentist’s office in New Plymouth.

The 41-year-old entrepreneur and her husband, Justin, have worked tirelessly for the past eight years to transform her sassy country-girl chic clothing-and-accessories line, Cheekys, into an online-only enterprise with millions of dollars in annual sales. She’s settling into the first real office that she’s had — with a door — since opening this facility in the tiny Payette County cow town in 2011.

“When my husband and my uncle did this office for me, they pulled pieces from my past into it,” she says. Decorative wood panels and the screen door came from Cheekys brand retail shops in Nampa and Mountain Home that have since closed.

Cheekys now employs 20 to 30 people and fills seven buildings in New Plymouth’s three-block downtown. They own four of the buildings and lease three.

Now employees don’t have to cross the street to fill an order.

Jonni Smith, who “does a little bit of everything,” pulls orders in the Cheekys warehouse in New Plymouth. Katherine Jones

Though there’s no longer a Cheekys storefront, having the buildings occupied has brought “a sense of life back to downtown,” New Plymouth Mayor Beth Earles says.

Roberts is dreaming of a day when she can tear down the deteriorating buildings and build a signature headquarters that customers from all over will want to visit, shop and hang out.

“We would like to build a retail facility and restaurant, and probably have offices above,” Roberts said, noting that’s in the business’ five-year plan. “We would like to have a place that still fits the aesthetic of the town. I might throw a little bit of Southern country in too, maybe some hurricane shutters. I want to have a place that really embodies our brand.”

Roberts’ talent for modern marketing via Facebook helped her build relationships with potential customers all over the country and beyond. The business now has a loyal customer following on social media, including 400,000 on Facebook alone, whom she sells to directly online. Cheekys also wholesales to about 3,500 boutiques across the United States and abroad, primarily Australia.

Now a mentor to other small-business owners, Roberts shares some secrets to her success — and nearly catastrophic missteps — in a new book titled “Backroads Boss Lady: Happiness Ain’t a Side Hustle — Straight Talk On Creating The Life You Deserve.” Much more than a business “how-to” book, it’s an intimate memoir of her journey — about surviving child abuse and domestic violence, the emotional toll of a bitter custody battle over her twin sons, and her efforts to gain acceptance in a rural Idaho town of 1,500 people.

Saucy, edgy, irreverent and, well, a bit cheeky, Jessi and Justin Roberts set the tone for Cheekys, a multi-million dollar online business. Katherine Jones

Cheekys Brand, lifestyle and family

“Cattle, country music and cold beer on a hot summer night.”

That’s what Roberts says Cheekys celebrates through its Facebook community and its merchandise, which includes T-shirts, hoodies, cardigans, purses, hats, jewelry and so much more. The name of the business is a nod to Roberts’ irreverent sense of humor.

Here’s a flavor of the slogans printed on apparel and other items: “Country AF,” “Cowboys Lie,” “Kiss My Bass,” “Patsy, Loretta, Dolly,” “Don’t Bulls**t Me, Darlin’,” “The Higher the Hair, The Closer to Heaven,” ”Stronger Than a 5th of Whiskey,“ “Log it, Graze It or Watch It Burn,” “Bad Bitch Cattle Co. “and “Rural House Wives of America.”

“Our market is everyday people,” says Justin Roberts, who developed Cheekys’ high-quality T-shirt screen printing operation. “We’re not high class, we’re just regular working people ... country folk.”

Their automatic screen printing press is in a building behind their house — and it cost more than the house. Jessi works with manufacturers in China to make sure they have a steady supply of good-quality but affordable T-shirts, and she has in-house designers who create the words and images.

Jessi, who is from Texas, worked in car sales at a Saturn dealership as a young adult. While at a training in Nashville, she was recruited by a Boise dealership. She moved north for that job in 2000, but didn’t meet Justin until five years later at a Dodge dealership; he worked in the service department and she was an Internet sales manager. Both previously married, they had dated only a couple of weeks when they got married and moved back to Jessi’s home state.

“I guess when you know, you know,” says Justin, an early riser who grew up in Homedale. “I figured we’ll just go on an adventure, and we’ll work on the other details later.”

Jessi Roberts’ family is part of Cheekys, including her son, Hunter Crites, center, who smooths t-shirts on to the 12-palette screen printing press, and his best friend Tristan Echardt, who pulls them off and puts them into the drier. Katherine Jones

Jessi Roberts has three children from prior relationships: Hunter, 20, and twin boys Sterling and Jackson, 13. She and Justin have a daughter, Addy, 11. Hunter now manages Cheekys’ printing operations.

Roberts’ best friend, Trisha Meyer, a silent partner in the business since its inauspicious beginning in 2011 as a brick-and-mortar store with a tanning bed and a half-dozen purses, now runs Cheekys’ online auction from her home in Hawaii.

Auction items are primarily older merchandise that’s not carried anymore. It was started around Christmas one year, and so popular that they kept it going. More than 20,000 people are members of the auction page.

“That helped move 120 items each week,” Meyer says. She spoke by phone from her home on the big island. “That was the biggest part of the business in the beginning — it made more money than the store did.”

Another clever, fun way that Cheekys promotes some of its new merchandise is through a monthly Bitty Box, now called the Chicks Fix, a themed box with one clothing item, one piece of jewelry (or item of equal value) and one mystery item.

“Nobody sees anything. It’s all a big surprise,” Meyer says.

They share new merchandise and build rapport with customers during daily Facebook Live videos. Jessi is camera shy, so Justin is often the one on camera holding up bath bombs, cosmetics bags, and all sorts of girlie and blingy things. Their banter is light, and they sometimes stop to sing someone “Happy Birthday” and answer questions.

The New Plymouth retail store did well over the years but the online business boomed. Between 2013-17, Roberts also opened a Nampa shop at the Karcher Mall, and licensed others to run New Plymouth, Mountain Home and Fruitland shops. But for various reasons, all of the shops closed. People say they want to shop local but they often prefer the ease and cost of buying online, Roberts said.

Roberts_BackroadsBossLady_Final Cover.jpg
Hachette Book Group, $24.30 at You can pre-order the book now. It comes out March 5.

Inc. magazine and a book deal

Roberts is a fan off Inc. magazine but she was frustrated that they didn’t feature mom-and-pop businesses in rural areas very often, so she reached out to the magazine’s social media coordinator.

“There are a lot of us out there, and we would love to have a place to look up to,” Roberts recalls telling her. “And I just feel like you’re missing that huge group of people that could use some inspiration and insight into business.”

That led to a couple of articles in the magazine, including one headlined “How This Former Outback Steakhouse Waitress Built a $2.8 million Retail Brand,” and also an introduction to a book agent. Roberts was skeptical at first, telling the agent she wasn’t interested in buying 10,000 books, storing them in the garage and trying to sell them.

But she was persuaded that wouldn’t happen — and she was invited to meet three professional ghost writers to help her with the book. She chose Atlanta-based writer Bret Witter, who co-wrote the book “Monuments Men” with Robert M. Edsel, which was make into a feature film starring George Clooney and Matt Damon. He traveled back and forth to Idaho during the writing process.

Multiple publishing houses competed for the rights to her book. She chose Grand Central Publishing, part of the trade publisher Hachette Book Group.

The book comes out March 5.

Roberts was not comfortable sharing the financial details of her book contract. But she said what she received is substantial, roughly equivalent to a month of her business revenues — and she spent way more time than that on it over the past year and a half.

She initially viewed the book as a form of long-term advertising, more appealing than offers she had received to go on reality TV shows or the popular “Shark Tank.”

“You can do a news article or a radio blurb. But a book has, no pun intended, more shelf life,” Roberts says.

But while writing the book, the project turned into an emotional journey as she reflected on many painful and difficult aspects of her personal life and business.

“I get very honest about domestic violence and child abuse,” says Roberts, who admits in the book that she was prodded by Witter into disclosing some of those intimate details. She doesn’t hold back, sharing detailed anecdotes about her life and others close to her.

Jessie Roberts recognizes some of her Cheekys followers during the daily Facebook live and banters with them as well as her husband. Katherine Jones

‘I don’t want praise with an asterisk’

Roberts was born on Whiteman Air Force Base in Missouri but she grew up in West Texas. She described her mother as a drug addict who worked as a dancer in gentlemen’s clubs from the Dallas-Fort Worth area to Abilene.

“My mom and I lived in a lot of abandoned homes,” she says. Her father often had trouble finding her.

She tells in the book that a man who her mother worked and lived with sexually abused her from ages 2 to 11.

“I know others knew of the abuse because others were involved. Nobody did anything to stop it, not even my mother, until I finally told my father’s new wife what was happening to me,” she wrote in the book. “That’s when she and pops refused to send me back ...”

In her early teens, she was unable to adjust to living with her father or grandparents because by then she felt like she didn’t need parenting. Her grandparents put her in a Presbyterian girls home. Just before turning 16, she got her own apartment. She paid her rent with money she earned working at a San Antonio pizza business. She dropped out of high school her senior year.

“I don’t remember when I first learned how to pray. I don’t remember when God came into my life,” Roberts says. “But I really do feel like there was this seed that was planted in my brain that was like: ‘I’m going to give you what you need to know, and you’ll be able to take care of yourself.”

She’s not sure if that “seed” she needed to survive was a divine gift or from mentors she’s had.

“Maybe it was both,” she said.

In one moving passage in the book, she wrote why she was reluctant to reveal the abuse she suffered as a child:

“I’m already afraid people will read this book and say, ‘Jessi’s done all right ... for a woman,’” she says. “Jessi’s done all right ... for a high school dropout ... for a country girl ... for someone who just sells clothes and junk and woman stuff.

“I don’t want people to say, ‘Well, dang, Jessi’s done all right ... for a sexual assault victim’.

“I don’t want praise with an asterisk. I don’t want to be graded on a curve. I want to be called what I am — a businesswoman, a Boss Lady, an amazing mom, a faithful partner and wife — and I want to be judged, if you have to judge me, on Cheekys, which I am damn proud of, and which is my heart and soul.”

In the author’s note at the end of the book, she encourages anyone suffering verbal, psychological, emotional or physical abuse to talk to a loved one or call the National Domestic Violence Hotline: 1-800-799-7233 (SAFE).

Jessi Roberts is a small-town Idaho entrepreneur with a big online customer base. She’s the owner of Cheekys, a multi-million dollar online enterprise, which occupies several non-descript storefronts in New Plymouth. Katherine Jones

Meet the ‘Boss Lady’

‘Jessi Roberts will sign books at a launch party for “Backroads Boss Lady” at 7 p.m., Tuesday, March 5, at Boise Barnes & Noble, 1315 N. Milwaukee St.