Backroads Boss Lady

Backroads Boss Lady
Happiness Ain’t a Side Hustle—Straight Talk on Creating the Life you Deserve. (Jessi Roberts), founder of Cheekys

This book grew out of an article in Inc magazine, “How This Former Outback Steakhouse Waitress Built a $2.8 million Retail Brand.” When my agent brought it to me I thought, Eh, maybe. Then I talked to Jessi Roberts.

Oh yeah, she’s good. All the way good: good mom, good person, good friend, smartest person about business I’ve ever met. Most people I work with are at least 10% bullshit. They are less than they say; they got more help than they acknowledge; they are selfish where they claim to be giving. That’s human beings! But if anything, Jessi is more than she says (or even knows) she is. Started at the bottom now we’re here? Please. You have no idea what the bottom looks like until you’ve read Jessi’s story.

This isn’t a business book. Yes, it will help you run, work at, or manage a business better. (She’s smart, ya’ll.) But I hate business books. I would never write one. Backroads Boss Ladyis Jessi’s story, with all the tears and cheers. It’s not about money. It’s about never giving up and always looking for the next way to make your life, your family and your community better—no matter what you’re doing or where you live. It’s about taking charge. It’s about not making excuses. It’s about valuing your friends, because they are the ones who will be there when you break down in tears.

If you live in a small town—especially if you are a woman—read this book, because it’s your story, too. If you live in a large city and want to understand what is happening in the rural areas of America, read his book. This isn’t some Hillbilly Elegy crap where the writer goes to Yale, lives in San Francisco, and looks back at his hometown from that distance and height. Jessi Roberts is so firmly ensconced in her little town of New Plymouth, Idaho (population 1,538) that you couldn’t crowbar her out—and people have tried. She loves New Plymouth. Loves rural life. Loves the 500,000 rural sister’s she met as she’s turned her little bitty store into a world-wide social media gathering site and retail hub. She’s writing what she’s living, and she’s living what she knows.

There’s that famous quote from Ginger Rogers about doing everything Fred Astaire does, but backwards and in high heels. That’s what Jessi’s story reminds me of. It’s way harder making it as a blue-collar rural woman, but you get a lot less credit. The reason I love this book is that it never dwells on that, because Jessi believes so whole-heartedly that no matter the hardships, there’s nothing better than the dance.


If you hit a period where you can’t go another step, this book will make you feel like running a mile.

#1 New York Times bestselling author Lee Woodruff

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, author of The Myth of the Nice Girl
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