Entrepreneurial memoirs mete out their share of dark days before the blazing sun of success illuminates the final chapters. Jessi Roberts's memoir, however, is harrowing almost to the end. Every moment of joy and triumph Roberts experiences in the process of raising her family and building her Western fashion company Cheekys into an $11 million brand--and a 2018 Inc. 5000 honoree--seems ridiculously hard earned. Yes, starting a business is difficult. But does life have to be this difficult?

Roberts asserts from the start that Backroads Boss Lady: Happiness Ain't a Side Hustle--Straight Talk on Creating the Life You Deserve, isn't a business book. That said, there is lots of good business stuff in it, of the here's-how-things-work-in-the-real-world variety. If you want to know how to merchandize a Main Street store or kill it at a trade show or decide whether to hold 'em or fold 'em when beset by copycats, Roberts has been there and done that. She doesn't treat entrepreneurship as glamorous. Hers is a world not of unicorns but of mules. (Specifically of "Mollys"--female mules that are the smartest, most stubborn in the herd. Roberts says she identifies.)

Roberts explains in the introduction that she wrote Backwoods Boss Lady to inspire and instruct ordinary women like herself to find happiness and fulfillment. "I want you to say, 'If Jessi can do it, I can too,'" she writes. Given the obstacles she overcame, for most readers that may be so. As Roberts gradually reveals her personal tragedies between descriptions of trips to the Dallas wholesale market and tutorials on Facebook marketing, Boss Lady feels like a timed-release version of the Book of Job.

Roberts grew up with an addict mother whose criminal boyfriend raped, beat, and psychologically abused her from the age of 2. She was committed to a state home for troubled girls, from which she ran away, dropping out of high school. She left a husband who cheated on her shortly after she gave birth. She lost custody of her twin sons following a vicious rumor campaign stoked by their father--an ex-boyfriend. There are repeated brushes with poverty. Endless slights by people in her adopted hometown.

And yes, there are fist-pumping successes, deep friendships, kind supporters, and (at last) a near-perfect husband and nights under the stars in her New Plymouth, Idaho backyard, from which she can see mountains. But this is, first and foremost, a survivor's story. Readers will cheer for Roberts. They will be inspired by her. And they will worry about her.

How business became personal

Roberts decided to make her life a teaching moment after Inc. wrote about her two years ago. She had reached out to us on Facebook describing her company and saying she'd like to see more coverage of rural businesses. Our social-media editor followed the link to Cheekys' Facebook page and fell hard for a photo of a beer cozy (the image of a bear with antlers and the word "Beer" emblazoned on its side, which tells you all you need to know about the company's sense of humor). The lead went to me because I write an online department called Main Street.

Cheekys, at that point, was just marginally a Main Street business. Roberts had closed her original store in New Plymouth and repurposed the building as a warehouse and office space. One retail outlet remained in a nearby town. But most of her business was conducted through online sales, a surprisingly successful internet auction, and wholesale to more than 600 boutiques, many of them in small-town America. In the book, Roberts explains the decision to be a brand rather than a brick-and-mortar store: for business reasons, sure, but also because some folks in the town where she'd set up shop had trampled on her reputation, her family, and her heart.

When I first spoke to Roberts in 2017, she was funny and brassy and colorful. She related many great stories that appear in the book--for example, how in the early days she and her second husband, Justin, transported apparel to sell at rodeos in stock trailers from which all the poop hadn't been removed. Then (let's stay with that theme) there's the one about how they broke through with a shirt bearing a picture of a Hereford and the slogan "Don't Bullshit Me Darling." She alluded to a few personal hardships. But nothing sadder than the lyrics of your average country song.

It turns out Roberts hadn't intended Boss Lady to be much more revealing. I caught up with her by phone at a Las Vegas trade show, where the dry air was playing havoc with her throat. She explained that she had set out to write a straightforward business book for mom-and-pops, especially those in rural areas. "Oftentimes when I read business books, there is a lot that doesn't apply to me," she says. "I don't have a boardroom. I have a bathroom that I have to clean."

Her instinct had always been to obscure her past. "It's a lot for people to take in," she says. "And it's scary to be that vulnerable." But then she enlisted as co-author a professional writer named Brett Witter. As they talked, Roberts found herself returning to the theme of women who never believe they are good enough. "They get into this race where they compare themselves with other people and feel bad about themselves," she says. She told Witter how that played out among her employees and how it played out in her own life. Roberts decided that only by exposing the whole story could she give women perspective on their circumstances and potential.

What she learned

We talked about developments since the book's bittersweet conclusion. Roberts--who previously shunned the limelight--has become something of a brand in her own right, giving speeches and readings and mentoring other companies.

The chaos quotient is down, but mess remains. Not long ago, a wholesaler (called "Q" in Boss Lady) whose machinations almost destroyed Cheekys, resurfaced and tried to sue Roberts over a complicated issue involving product designs and commissions. (Thanks to new friends in the legal community, she was able to put the kibosh on that.) She now has custody of one twin, Jack, while the twins' father retains custody of the other, Sterling. Separating them "is heartbreaking," she says. "But I can't lose the opportunity for Jack to have a normal, non-chaotic home."

Personal traumas are not all that Roberts addressed for the first time in Boss Lady. The book is full of useful pointers for retailers and manufacturers--potential competitors included--such as the bargains to be found on Harry Hines Street in Dallas. Roberts says she was surprised how comfortable she felt disclosing those things. "Someone else knowing how or where I do business isn't a threat to me anymore," she says. "I'm confident enough that I don't have to have a secret weapon."

Roberts says she learned a lot about herself as she and Witter worked on the book. But one of the most gratifying revelations occurred more recently, when she gave a reading in Abilene, Texas, and 20 relatives turned up to support her. Among them was a cousin with whom she had been close as a child, back when Roberts was the small, silent victim of her mother's boyfriend.

The cousin reminded Roberts of her early entrepreneurial inclinations. She asked, '"Do you remember when we were 6 years old and you had this die-hard plan that we were going to buy a bus and drive it around the United States and teach people how to dance so they could be happy?"

"And I realized that had always been inside of me," Roberts says. "And I thought, that is so cool!"

Published on: Mar 25, 2019