Backroads Boss Lady

Happiness Ain't a Side Hustle--Straight Talk on Creating the Life You Deserve


By Jessi Roberts

With Bret Witter

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$16.99 CAD

This item is a preorder. Your payment method will be charged immediately, and the product is expected to ship on or around March 5, 2019. This date is subject to change due to shipping delays beyond our control.

Read the inspiring story of a mother of four who faced down her hard past, poverty, and self-doubt to create the life she dreamed of, including owning her own multi-million dollar business–in this book that’s “filled with grit, humility, common-sense advice and entrepreneurial wisdom” (Lee Woodruff, #1 bestselling author).

New Plymouth, Idaho. Population 1536. It doesn’t look like much from Rural Route 30, but it was here, in this quiet town, that Jessi Roberts created something unexpected: the kind of life she always wanted and a multi-million dollar, for rural/by rural business empire.

The business is Cheekys, which started with 6 purses and a tanning bed. Now in her book, Jessi shows how she grew one small store hurdle-by-hurdle into a national clothing and accessories brand with a 1.5 million strong community. Best of all, she did it by standing tall for her values: always be kind, lift up the next gal, and treat employees and customers like family.

A personal story filled with life and business tips, BACKROADS BOSS LADY is about embracing your passion even when others don’t see value in it–or you–and about putting food on the table and believing in yourself. Brimming with authenticity, it gives the warts-and-all, love-it-despite-it skinny on rural life, community, and contentment without compromise.



Looking for some support ~ I am really needing a place to reach out and am hoping this is it!!

For those of y’all who don’t know me I am Jessi and am the founder of Cheekys aka The Bosslady ~ and wow things have gotten crazy around here… I kinda feel like when I was young and had too much to drink and needed to put one foot on the floor!

This last year we had HUGE growth. I started this baby in 2011 and that was only because I knew I wanted to do something in my tiny town and I didn’t want it to be a laundry mat. And in Jan of this year we did as much business as the entire year of 2014. Each month we have increased at least 20 to 100% in growth. We have had to get new machines for printing (which led me to realize how expensive power is and how much weight an old building can hold), we have overloaded the PO [post office] in our town and have no idea what to do there, we have hired 30 plus people to help us… and the list goes on and on.

So in 2016 we were featured by Inc. magazine and then shortly after I was contacted by several publishers about having a book. That contract is now signed and my writer (who is helping me a ton) shows up tonight to stay for a month. Let me tell ya writing a book is NOT at all how I thought it was. We are getting contacted constantly about TV shows, reality TV, movies and all kinds of stuff. They just can’t believe that we have this business in such a small town and that it’s grown the way that it has.

I still love all the designing aspects; the manufacturing is my all-time favorite. I LOVE to help other women and am working on a consulting/mentoring program now with a few gals. And it’s what I really want to do. I am hoping my book will do that for women on a budget, women who just have questions and hope it moves them. I have let a handful of women in this group read the first book proposal and it seems to be headed down the right path.

Okay, all that being said… I am in a bit of a whirlwind. I still am so involved in everything down to the tissue paper we use. I am kinda overwhelmed by all this attention. I prefer to be behind the scenes… I love typing but not being live or on TV. It’s scary to be so vulnerable and exposed. Living up to the perception people have is hard. I am not fashionably dressed, I don’t do a lot of makeup, I am in a bun most days… I am overweight. I don’t have loans or a line of credit, I cry like once a week (half good tears, half the time sad)… this voting finals thing [for boutique of the year] has me thrown for a loop. I am sooo proud of all the girls on there and sooo many of them carry our line which makes me even more proud. So I guess my question is: how do we stay sane, stay private, how do we give our opinions without sounding like a bully or arrogant? These are the thoughts I have everyday… please tell me I am not alone.

SS: First of all can I say that you hardly wearing makeup, having your hair in a bun, and being overweight is 100% relatable and what all of us women REALLY want to see…
KWB: I want to hug you…
GB: I am proud of what you have accomplished and especially from a small town…
VCW: Omgah Jessica Dawn Roberts… such a freaking amazing and inspirational story. YOU are who so many of us strive to be…
LM: I don’t have any advice really but I just want you to know how happy I am to have found Cheekys…
VS: You are so not alone!!

You know what, girls? It’s been more than a year since I wrote that post, and I’m still terrified to put myself out in the world. There are things in this book I really don’t want to talk about and things I am terrified for you to know. But it’s support like this that makes me feel like I can—and that sharing my life and advice can do some good in the world. So to everyone who bought from Cheekys, wrote to Cheekys, and posted on Facebook asking for support. To all the boutique owners and the moms-in-business and the small town girls working for it every day… thank you. I love you. This book is for you.



That’s the first question my publisher asked, after they said they wanted to work with me (celebration time!): “Is this a business book?”

Understand, I hadn’t written it yet. They had read a twenty-page proposal that grew out of a small article about me in Inc. magazine titled “How This Former Outback Steakhouse Waitress Built a $2.8 Million Retail Brand.” So obviously, business was important.

But is this a business book? No. Not really.

Don’t get me wrong. If you are looking for business tips, you will find them here, especially if you own, manage, or work at a small business. After all, I went from a tiny store in an even tinier town to owning and running a multi-million-dollar national brand. So I have tips, and lots of them. I have “life experience,” as they say. Everything I know about selling I learned in the car business. Everything I know about running a boutique I learned by trial and (so, so many) errors. I’ve had to learn how to find products for nothing and make an extra twenty dollars a day to put food on the table for my kids. I’ve also had to learn how to design and manufacture on an international scale, wholesale to three thousand boutiques, and manage thirty employees. In other words, I’ve learned a lot.

But this isn’t one of those “ten things that will make your business explode” books. I don’t have a set of principles to unlock the secret of success, right now, in all your life’s ventures. I don’t want to shift paradigms or scramble business logic. I’ve never been invited to a TED Talk. They don’t want someone like me. I never went to business school. In fact, I dropped out of Robert E. Lee High School in Midland, Texas, two months before graduating. My business advice works, because it’s had to work. I didn’t have the luxury of failure.

But there is so much more to my story. I’m a working mom from a lower blue-collar background (and that’s putting it mildly). I live in a horseshoe-shaped town in Idaho. I’m from the country, I sell clothing and accessories to women in the country, and I love being from, in, and for the country. Thanks to some book called Hillbilly Elegy, there’s a perception in cities like New York (where my editor lives) that people in small towns should be pitied, because we’re too stupid and lazy to know our lives would be better in the city. Well, I don’t believe that at all. I’ve lived in Texas. I’ve lived in Boise. I live in New Plymouth, Idaho, population 1,538, because I want to live here. I want to raise my kids here. And I run a company for all the women in all the little towns like New Plymouth who feel the same way.

This book isn’t for the CEOs, the Wall Streeters, or the TED Talkers. It’s for the mom-and-pops fighting for the money to open tomorrow. The business owners working fifteen hours a day, six days a week, to put food on the table. The wives running companies out of their bedrooms to keep their families afloat. The moms working double shifts and selling cosmetics on the side. The factory workers. The mail carriers. The people living on the backroads, and I don’t just mean in rural areas, I mean any place that is overlooked and discounted, where the hustle is harder and each dollar means more. Most of us don’t get $10,000, and definitely not $100,000, to get started on our dreams. Most of us don’t even get emotional support. So this book is for you: the strivers, the hustlers, the never-give-uppers who never had savings, investors, or outside help, because that’s my story, too.

This book is for the moms working sixty hours a week selling cars or slinging trays so their children can have a better life. I’ve been there. I know how it is. I know it can feel like people look down on you, no matter how successful you are. I will never look down on you, girl. You’re my hero.

Being a Boss Lady isn’t about money, after all. It’s not about glamour—thank God, because I am the opposite of glamorous—or a big idea that changes the world. I didn’t start an Internet company. I didn’t even start a website, although I have a very successful one now. I founded a retail store, in a small brick building with a big plate-glass window, across the street from the Double Diamond Saloon. That seemed like such a bad idea even the local bank wouldn’t give me a loan. They said, “You can’t open a shop in New Plymouth, Jessi. There’s so little traffic we drive lawnmowers down the main street.”

“Sure,” I said, “but only during the co-op races, and that’s two days a year.”

They still said no.

I built Cheekys anyway, and to this day, despite more than $20 million in sales, I have never been approved for a bank loan for my business. I have never been offered money by an outside investor, although my best friend (we were single moms together) has been a silent partner since day one. I still run the business out of New Plymouth, even though it has exploded worldwide. In 2012, Cheekys’ total revenue was $43,000. For the year. That’s gross, not net. Six years later, our revenue is $125,000 every week. Our sales are increasing by more than $100,000 a month. By next year, at our current growth rate, we’ll hit a million dollars a month in sales.

Now let me be clear: that doesn’t make me rich. I still don’t have money in my bank account or the backyard pool I’ve been dreaming of since I was a little girl. Okay, I have a pool, but it’s the collapsible aboveground kind from Bi-Mart, which my husband says is barely better than the way we did it when we were kids: rainwater in a stock tank. (I don’t wanna spend this whole book explaining terms, so if you’re in the city and don’t know what a stock tank is, get your Google on.) My husband and I, who both work at Cheekys full time, make $2,000 a month, and we only started paying ourselves in 2016. At one point, Justin became frustrated by that. Our Yukalade—the half Yukon, half Escalade body-shop special we’d been driving for ten years—had broken down again.

“Jessi,” he said, “everyone who works for Cheekys has a new car but us.”

“Yup,” I said. “And we provided those opportunities, Justin. We helped those families thrive. Doesn’t that make you feel good?”

Call me crazy, but I take more joy in knowing Erika can care for her five children, including two she took in after her brother died of cancer way too young, and the other Erica can buy a minivan for her growing family, than I ever would in a swimming pool.

That’s why I invest almost everything Cheekys makes back into my business and my community. That hurts me financially, I suppose, but it makes me rich in the things that matter more than money. I give my four children, ages ten to eighteen, a comfortable home with plenty of love and attention. I set a good example of hard work, kindness, and entrepreneurship. I work with my husband every day (in different buildings, to keep the marriage going!). I provide a good living to thirty employees, mostly women, who make me laugh inside our anthill, as we call the warehouse and order center, even when the orders are piling to the ceiling. Soon, if things go as planned, I’ll have a new warehouse and an expanded 2,800-square-foot destination store in New Plymouth (twice as many feet as residents!) to provide a retail anchor and community gathering point and, hopefully, bring thousands of visitors to this gorgeous, struggling, frustrating, infuriating, perfect little town.

And I have my Chicks—the thousands of mostly rural and small-town women who are fiercely loyal to the Cheekys brand. I don’t advertise much, except on Facebook. I don’t pursue publicity. Every order is checked by me and processed by my staff, even though we now have more than 50,000 individual customers and 3,000 stores carrying the Cheekys line. I’ve grown my business on word of mouth by offering clothing and accessories that small-town women love, but I’ve succeeded because I offer something they want even more: respect for their lifestyle and a personal connection. Cheekys isn’t just a boutique. It’s a worldwide community that celebrates small-town life and helps ordinary women see the beauty inside, the opportunities outside, and the value of who they are.

In other words, I set out seven years ago to feed my six-person family, and to help my small rural community, and I ended up building a family bigger than Boise. It has not been easy. It’s been a struggle. The journey has been gritty and desperate, and at several points I almost failed. I’ve had my family shattered and my confidence shaken. I’ve been attacked so ferociously that I’ve had to build my love (and I have a lot of love for the people in my life) out of the pieces of my broken heart. I’ve made a million mistakes. I make mistakes every day. But running Cheekys has been the most rewarding “job” I’ve ever had. These Chicks are my family, and you know I am proud to be the Head Mother Clucker to this brood of hens (and a few roosters, too). I’m proud of what we’ve built. But I’m even more proud of the way we did it, with respect for one another, a ton of hard work, and love for every person, even the haters who put us down.

So, no, this isn’t a business book. It’s a book about a business. It’s a book about family: the one you have and the one you create. It’s a celebration of small-town life, but it’s honest about the downsides, too. It isn’t a guide. It’s a story. My story. The Cheekys story. I’m writing it because I want you to say to yourself, “If Jessi can do it, I can, too.” The word it doesn’t mean start a small business, although there are plenty of tips for that here. It means grabbing hold of your personal dream and living your Boss Lady life.

I want everyone who reads Backroads Boss Lady to feel the way I feel every night, when I sit in my U-line camp chairs in the backyard of my farmhouse two miles outside New Plymouth, Idaho. From there, I can look over the alfalfa fields of my neighbor, Dave, to the steep yellow cliffs that climb toward the Sawtooth Mountains. It’s a gorgeous sight. I’m from West Texas, a place that pretty much defines the words flat and empty; I still can’t believe I get to look at mountains every day.

But I can also see my little round collapsible swimming pool, and our print shop five feet behind it, and the cargo containers on the edge of our gravel parking pad. I can see the two Traegers smoking dinner and the new outbuilding my husband is building—he keeps calling it a “man cave” for some reason, even though it’s obviously a “hen den”—and the pile of scrap lumber he left next to the six-foot-tall “chicken mansion” he built for our six layers last year, complete with plastic chandeliers.

The younger kids are swimming or running around. My eighteen-year-old, Hunter, is shambling off with his best friend, Kolby, who’s basically been living with us. Friends are over drinking Coors Light with Clamato juice in it, which Justin claims is an old Idaho tradition. The mosquitos are biting, but it doesn’t matter, because we’re laughing about what happened at work that day, and answering Facebook requests from Cheekys customers, and talking about what we’re going to do in the anthill tomorrow, because most of the friends who come over at night are the people I work with every day. I’m sure there is a book that tells you not to invite your employees to your home, but I can’t imagine living any other way.

This is Boss Lady, y’all—even if the pool is above ground. This is happiness. This is what the dream looks like for me and millions of others like me. And it’s here for you. It’s not impossible. Anyone can achieve it. No matter where you live, where you come from, or what you’ve been through, you can have your own house and your backyard barbeque and your chicken mansion, by which I mean whatever you call success. It takes hard work. It takes smart work. It takes staying true to your values and never giving in, but this is America: anything is possible.

Especially in Idaho.



Payette County, Idaho, is an hour northwest of Boise along Interstate 84. For the first twenty minutes of that trip, the drive is through suburban communities, with the steep desert mountains known as the Boise Foothills off to the right. Past Caldwell it becomes rolling farmland—mostly the deep green of sugar beets up against the dry sagebrush of the high plains—and then eventually the scrub prairie of the open range. The Bureau of Land Management (BLM) land is green in the spring but yellow most of the year, and empty except for the occasional herd of cattle local ranchers have paid the government to let them graze. On the left, it’s rolling land forever, without even a tree; on the right, the mountains are like cliffs, rising a hundred feet to a flat plateau, with the jagged purple peaks of the northern Rockies in the distance. It’s beautiful, but for me the most welcome sight is the small turbine power plant that comes suddenly into view, alone on the range at the top of a long rise, because from there the road dips down into the Payette Valley, the first place in my life I’ve comfortably called home.

The Payette Valley consists primarily of small farms crosscut with canals leading from our two local rivers, the Payette and the Snake. The valley used to be covered with apple orchards; now it’s mostly cattle ranches, dairy cows, and field crops. No potatoes (that’s eastern Idaho), but plenty of corn, peppers, pumpkins, and onions, along with alfalfa fields sprouting blue flowers in the fall and bright yellow mustard and canola fields and the sharp green mint that make the valley smell like breath freshener when it’s cut. Payette is the biggest town in the area, with 7,500 residents. Fruitland, with a population of 4,500, is the fastest growing. Some old-timers grumble that the Fruitlanders think their shit don’t stink because they have most of the new construction, but why pick a fight? I like Fruitland. They’re country like the rest of us, and they have my favorite coffee shop. It’s a drive-through window connected to a garden center. Half the population in the valley is Mormon, and Mormons avoid caffeine. For the rest of us, coffee is life.

My town, New Plymouth, is the smallest in the area and the farthest from the center of things. It was founded in 1898 as a utopian farming community by businessmen from Chicago who thought irrigation canals were the next world-changing innovation. They built their “New Plymouth” (our high school team is the Pilgrims) in the shape of a horseshoe so each homestead could have access to a large field fed by canals. The three-block commercial artery, Plymouth Avenue, cut the short way through the center; the industrial area sat between the horseshoe’s open ends. Little two- and three-bedroom houses soon filled in the rest. Even back then, New Plymouth was famous for the wooden waterwheels that lifted water out of the irrigation canals.

One hundred twenty years later, New Plymouth is that rarity of modern life: a town that’s basically the same as it was in 1900, even if only three of the original twenty-two waterwheels remain. Back when Plymouth Avenue was part of the fastest route between Portland and Boise, the downtown was full of shops, but after they built the freeway six miles away in 1957, New Plymouth slowly returned to its origins as an isolated farming community. There’s a small open-sided lumber mill that halves standard-cut boards with hand-fed band saws; on the other edge of town, there’s a small fertilizer depot for local farmers. Otherwise, it’s two bars, a bank, a gas station, two restaurants (the burger place has been for sale for three years), a farm co-op, and a liquor store inside a three-aisle market. One block of our historic one- and two-story downtown was leveled to build the tan stucco headquarters of our largest local company, a web portal called The rest looks almost exactly like it did in the photographs of New Plymouth from the 1920s. The town has almost as many churches—fourteen—as businesses.

I didn’t move here for the businesses or the churches. I like to joke that I came here to retire. (Ha!) My husband, Justin, and I met in Boise, but we lived in Texas for our first two years together. I grew up there, in Wichita Falls. I was used to the hard, flat emptiness of the west Texas desert, where it’s a hundred miles to the next town with nothing much to see in between. Justin hated it. He grew up on his dad’s ranch outside Homedale, Idaho. He liked the high prairie. He liked being rooted. He liked Clamato juice in his Coors Light. It was too hot in Texas for a guy raised with snow tires on his pickup truck.

So we moved back. After a year of being unsettled—staying with friends, working on a car lot to make ends meet, you know the drill—we leased our dream home. It was next to a dairy farm about a mile outside a little no-stoplight town I’d never heard of called New Plymouth. The dairy meant poop, which meant flies, especially when the wind wasn’t blowing, but the house had four bedrooms, a long driveway, and plenty of land.

In Texas, I worked full-time. I had been working full-time to support myself, in fact, since running away from home at fifteen. I eventually dropped out of high school, rented an apartment with no furniture, and slept on the floor. I had no friends in Texas. No family relationships I hadn’t burned to the ground. I was an outcast kid, the kind local people had pointed at with suspicion since I was six years old, no matter what I did or how hard I tried, and I was tired of it. I saved enough money for a bus ticket. I went to the library and found the town with the youngest and most educated population in America. I wanted to party with those kind of people.

I got off the bus two days later in Provo, Utah.

Provo’s a Mormon town. They don’t have liquor stores. They don’t have bars. They don’t even drink caffeine. I couldn’t believe it. I said, “What do y’all mean, y’all don’t drink Dr Pepper? Everybody drinks Dr Pepper.”

Within a year, I was back in Midland, Texas, working forty hours a week at a jewelry store in the mall, and I’d worked full-time ever since, even as I became a mother four times over between the ages of twenty and twenty-eight. I was working right up to the day Justin and I left Texas, when my youngest was two months old. I was managing a used car lot in Odessa for the man who gave me my big break in the car business after I left my first husband at twenty-two. (He cheated while I was pregnant. We’ll get to that.)

Justin is a worker, like me. He had been spraying pickup bed liners as a side job since he was twenty-one. In Texas, he was Mr. Mom to our four children, three still in diapers, while resealing industrial storage tanks in his spare time. We decided that in Idaho, with a partner, he could turn his sealing experience into a business. That’s how I “retired” to the easy (yeah, right) job of being a full-time mother to four children and Justin’s office manager, taking calls and handling the business accounts out of our house.

I couldn’t believe it. I got to be mom! So many women complain about watching the kids, but for me, it was a dream. I’m not a Mormon, but I know their faith well, and I love their emphasis on family. Every night, they have something called the Family Meal, where everybody sits down over food and talks. I never had that as a child. My mother never cooked me a sit-down meal. But ever since Provo, I had wanted that kind of family.

It took me fourteen years, but finally, here I was! A house. A husband. The time and space to be a mom. My oldest, Hunter, was in middle school and obsessed with video games, but Jack, Sterling, Addy, and I lived all four seasons outside: long walks in the summer, climbing hay bale mountains in the fall, snowball fights all winter. That spring, I planted my dream garden, almost an acre of beans, tomatoes, corn, and every other vegetable you’d ever want. The kids took their tiny “tools” and gardened with me every day. Pretty soon, we had a few pigs we were always chasing down the ditch, a few LaMancha mini-goats the children absolutely loved, and a bull named Zeus.

We didn’t have much money, but it was more fun to make everything anyway. Justin and Jack built robots out of boxes, because even at four, that kid loved to build. When Sterling wanted a clown car he could ride in for Christmas, Justin stripped down a Little Tyke cop car and decorated it with colorful vinyl seats, a clown painting, an umbrella, and a honking horn. I stitched Hulk costumes out of green fabric and Justin painted on the muscles. Our kids lived in costumes. Sterling loved Spider-Man so much we called him Peter Parker for a year. Addy always dressed up like Sleeping Beauty. At Ponderosa State Park, Justin and Hunter, our Boy Scout, set up the tent, built the campfire, and caught fish for dinner. The park had trees to the sky, a massive lake, and a paved area where the younger kids could speed around on their training-wheeled bikes with their superhero capes flying out behind them. I mean, how perfect is that? I was an American housewife—the kind who cooked what she raised and canned so many vegetables her husband had to build her a bigger pantry. For a year, our family bowed our heads over my home-cooked meals and finished every prayer with one of the little ones piping in, “And thank you to Zeus.”

Zeus was delicious, too.

We’re country. That’s how we roll.

I thought we’d roll like that for years, maybe the rest of our lives. But it didn’t happen. Justin’s business failed.

When it started in 2007, the economy was booming. Work was plentiful, so Justin quickly hired four crews and financed specialized equipment and trucks. But profit margins were always slim. We bid so low on some projects, we barely made money. Even during the good times, the company was scraping by. That’s fine. Most small businesses operate day-to-day. But when the housing market crashed and took the economy with it, contractors started squeezing. We had to cut our prices or they were going to cut us.

Now there was no profit, so Justin and I doubled, then tripled our efforts to find more work. We took jobs in Montana, Nevada, and even Utah. Justin had a specialty license in bombproof coating (yes, it’s real, and it’s cool as hell). That brought in business, but he was the only certified bombproof technician in the company. That meant he had to be on every job site. By 2009, Justin was traveling 320 days a year for physically demanding work, much of it performed inside huge, corroded metal tanks buried underground. He had severe pain in his neck and back. He was sick with a cough and… severe digestive problems, let’s call it that. He was pushing his body to breaking, and we were still falling behind.


  • "With grit, humility, common sense advice and entrepreneurial wisdom, BACKROADS BOSS LADY serves up a manifesto on how to do everything from overcome haters to persevere in business. If you hit a period where you can't go another step, this book will make you feel like running a mile."

    Lee Woodruff, #1 New York Times bestselling author
  • "Cheekys, which has a warehouse and office in New Plymouth and a retail outlet in nearby Fruitland, is perhaps the hottest thing going in this region of tiny towns and farms near the Oregon border...Now women around the world wear across their chests the company's arch-yet-proud slogans.", "How This Former Outback Steakhouse Waitress Built a $2.8 Million Retail Brand"
  • "Jessi's story teaches us never to give up on our dreams. Filled with both inspiration and action, this book will get you back on the path to manifesting your greatest vision, in business and beyond."—Mike Michalowicz, author of Profit First
  • Backroads Boss Lady isn't a business book. It's real life, real emotion, and real inspiration for all women. Jessi Roberts proves once again that success isn't about money, it's about honesty, friendship, hard work, loyalty, and loving where you live, even when-or maybe especially when-times are hard. Those are lessons all of us can use every day."—Vicki Myron, #1 New YorkTimes bestselling author of Dewey
  • "Take it from someone who has advised dozens of business owners: Backroads Boss Lady is groundbreaking. Jessi Roberts breaks the mold of what a conventional entrepreneur looks like and shatters every ceiling. This is more than a business book; it's about family, parenting, friendship, community and living your best life with integrity." Fran Hauser, authorof TheMyth of the Nice Girl

On Sale
Mar 5, 2019
Page Count
296 pages

Jessi Roberts

About the Author

Jessi Roberts was born in West Texas. She lives in New Plymouth, Idaho, with her husband and four children. She is the founder of Cheekys, one of the few nationally recognized brands that celebrates rural life, country attitude, and family values.

Learn more about this author