Community//

Lift Your Legacy: When banks turn you down, build your life on your own terms anyway with Jessi Roberts and Rabbi Jacob Rupp

My success came when I focused on my whole life. It’s impossible to have a life or business that will last long term without contentment. Many people confuse being content with being complacent. I have had huge successes at work during my 20s but I came home to an empty house. Success to me is […]

My success came when I focused on my whole life. It’s impossible to have a life or business that will last long term without contentment. Many people confuse being content with being complacent. I have had huge successes at work during my 20s but I came home to an empty house. Success to me is not about the balance of my bank account, and wouldn’t you know it, the bank account grew as I became less obsessed with it.


Jessi Roberts is the CEO and Resident Boss Lady at Cheekys Brand, named among the top five boutiques in the world by the largest boutique trade association in the United States. Her new business guide and memoir, Backroads Boss Lady, will be published in March by Grand Central and is available for pre-sale on Amazon.

Jessi founded Cheekys in 2011 in the rural community of New Plymouth, Idaho. Today, she employs 30 staff in retail ecommerce and wholesale manufacturing operations. Cheekys engages more than 2 million people each week on its Facebook page, and Cheekys wholesale is carried in over 3,500 stores worldwide, and offers custom options for several wholesale and retail shops.

Thank you so much for doing this with us! What is your “backstory”?

I am the founder and CEO of Cheekys Brand, an online retailer and wholesale apparel company that manufacturers and designs products from New Plymouth, Idaho, population 1,538. To say I’m an unlikely entrepreneur would be an understatement, but I come from a long line of workaholics. With an untraditional education or business background, I’ve figured out how to grow my company, founded in 2011, into a multi-million dollar venture named #356 on the Inc. 500 list this year. As I explain in my new book, Backroads Boss Lady (Grand Central, March 2019,) my business works because it’s had to. I didn’t have the luxury of failure.

Being in business when you don’t have the fancy education or typical background is pretty interesting, to say the least. Even with $20 million in sales since our founding, the business has still never been approved for a bank loan. I set out seven years ago with my $7,000 in savings in an attempt to build a business that could feed my six-person family and give back to my struggling rural community. Today my extended Cheekys family is far bigger than Boise, the nearest “big city.” We engage nearly 2 million followers a week through our Facebook communities, and more importantly, we help our 30 employees and their families live the American Dream in a place where most folks struggle to make ends meet.

Can you share the funniest or most interesting story that happened to you since you began leading your company?

Well, it’s pretty funny that Cheekys started out as a tanning salon that sold a bit of clothing on the side! That sure didn’t work in a town like New Plymouth. The ladies didn’t want to tan, they wanted to shop! So we pivoted accordingly and the rest is history.

What was your biggest challenge to date either personally or professionally and how did you overcome it?

My book, “Backroads Boss Lady,” comes out in March 2019 and could probably be titled “Jessi’s Top 10 Biggest Mistakes.”

I have led a challenging life, as many have, and it’s been key for me to not let those challenges break me by being okay with them defining me. Yes, I grew up in a violent home, and we were often homeless. It was hardly a home at all. I’ve had some tragedies as an adult, but honestly the hardest part for me is to realize that I deserve the joy and success that’s in my life today. It’s a struggle every day to overcome my own doubts and vulnerabilities, but I’m still at it.

What does leadership mean to you and how do you best inspire others to lead?

To me, leadership is not just one task or even a small list of traits. Leadership is a lifestyle — literally the way you live your life. It can’t be done just in the office or just during the workday. It’s having a constant heart for others in your life, genuinely wanting to see them succeed, prosper, and grow in a life that matters to them. Leadership is a mindset, a relationship of servitude to yourself and to others. You can’t turn it off and on, or it will not inspire anyone because it’s not authentic. Creating understanding with people, listening to them, and empowering them is what leadership means to me. It takes clarity of vision, a compassionate heart, and self-awareness to be a true leader.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Every time I meet someone, I intend for that person to become a long-term friend or business contact. That’s the only way I’ve found to make sure the relationship is open, honest, and not one-sided. When you are looking for ways to serve others, that genuine help comes back to you in spades. I can’t list just one time that I have been helped. But I can offer that it’s essential to create a strong foundation with your staff, allowing them to really own their roles in your business. Especially with the lack of interest and support we’ve seen from banks, our success is a credit to our workforce. We’ve intentionally created a loyal team that feels positive about what they do everyday. We’re all motivated to make the business succeed.

It’s difficult to call out one particular person because so many people have supported me along the way, but my best friend Trisha has been a silent partner in Cheekys since day one — we were single moms together. Everyone needs someone who is on your side no matter what, whether that’s your mother, husband, best friend, or son or daughter.

Was it difficult to fit your life into your business/career and how did you do that?

I come from a bloodline of workaholics, so I didn’t realize there was more to life than work until early adulthood. I’m less enthusiastic about work-life balance than I am making sure the business serves me and my family, and that it brings joy to our lives. When I stopped trying to make money and get rich, things changed for me substantially. I started working to make my business serve my employees and me as well as it did our customers. Decisions were made with a different agenda. Joy flowed into the business and we eliminated anything that didn’t bring joy. I focused my attention on margins, putting employees in the right positions, and cutting the ones who didn’t add joy to our team. I’m happier at work and with my family as a result. I’ve learned that one thing doesn’t define my life, and the business is just one of many things…I fit the business into my life not the other way around.

Did you find that as your success grew it became more difficult to focus on the other areas of your life?

My success came when I focused on my whole life. It’s impossible to have a life or business that will last long term without contentment. Many people confuse being content with being complacent. I have had huge successes at work during my 20s but I came home to an empty house. Success to me is not about the balance of my bank account, and wouldn’t you know it, the bank account grew as I became less obsessed with it.

When I became fixated on my success as a mom, a leader, a friend, a designer, a mentor, the money followed. When you focus only on the money, you can’t focus on what makes the money or the work get done, and that’s what ultimately creates success. You can’t do both.

Can you share five pieces of advice to other leaders about how to achieve the best balance between work and personal life?

  1. I rock license plates on my “dream car” (now my real car) that say “Bad Mom.” It’s a constant reminder to me that I can only do so much and with a good intent and love, that will be enough. We may not always feed our families the most perfect organic meals, we may drop a kid off late to school once in a while, heck, we may mess up all the time, but giving your family a person who is happy and peaceful is 1,000 times better than being a perfect non-present parent or spouse.
  2. I take my children and spouse with me. My husband, Justin, is our CFO. My commitment is to my family, so as often as possible I introduce them to the work I do. I teach my children life lessons and entrepreneurship, letting them experience different lifestyles, cultures and even the everyday office grind from time to time. My spouse is proud of me when he sees the work I do. My children respect our business and help out often, (even with the trash.) We see and experience things together that create fun memories and open their minds. They aren’t always with me at work, but I bring them as often as possible. To me, it’s important to teach them things they may not learn in school, such as how to manage a schedule and learn life lessons from real experiences.
  3. Splurge on beds, recliners, bathtubs, your office chair, and only eat and drink things that you enjoy. Allow yourself to have things that make you comfortable and provide great rest. Do the same for those in your family. Oh, and get a housekeeper, because you don’t have time for that!
  4. Upgrade those tickets…but do your work before you go to the show or on the vacation. Be present in all things — present before work, at work, even present at home when you’re relaxing.
  5. Get rid of things that don’t bring you joy. From the rug that always turns up on the edges to the employee who is causing discontent by murmuring complaints, trim the things that take up a ton of time and simplify them. And hire out things that are not a good use of your talents.

What gives you the greatest sense of accomplishment and pride.

The other day, not one but TWO of my employees showed up with new cars. Around the same time, two of my employees were giving birth to their second babies (with their departments still running like clock work!), and my dad, my uncle, and my husband get to drive around on Bobcats while they build our new “chicken mansion.” It’s things like that which really make me feel #likeaboss. If your employees aren’t buying new homes, sending their kids to college or growing as families, then you aren’t a boss. It’s not about what I have, it’s what I have allowed them to earn.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I feel like Cheekys has become a movement and it’s one I hope to grow even more through my book, Backroads Boss Lady. I’m happy to have created a community where women can come together and feel pretty, on the inside and out, because of the kindness they share with someone else. My community is mostly rural women and I’d like to see more urban women join us. Too many people don’t feel like they are worthy of success, love or joy, regardless of where they live. That is heartbreaking to me. I would start a world-wide movement where everyone could know their worth and see and honor the worth of others.

What is the best way for people to connect with you on social media?

Facebook! Almost every day we go live and reach about 1.5 million people through the business’s main business page. I am always up for sayin’ hi on there! Instagram is a close second. I love meeting new people.

    The Thrive Global Community welcomes voices from many spheres. We publish pieces written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Learn more or join us as a community member!
    Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

    You might also like...

    Community//

    “I believe that no matter what your profession, you are the CEO of your world” With Kathryn Brooks

    by Akemi Sue Fisher
    Community//

    5 Things You Need To Know To Succeed in The Fashion Industry, With Kathryn Brooks

    by Yitzi Weiner
    Brian A Jackson/Shutterstock
    Wisdom//

    11 Life-Changing Lessons From Amazing Leaders

    by Marina Khidekel

    Sign up for the Thrive Global newsletter

    Will be used in accordance with our privacy policy.

    Thrive Global
    People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.

    - MARCUS AURELIUS

    We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.