Jessi Roberts, Founder of Cheekys

Jessi Roberts, Founder of Cheekys and author of Backroads Boss Lady
Jessi Roberts, Founder of Cheekys and author of Backroads Boss Lady

Jessi Roberts, Founder of Cheekys and author of Backroads Boss Lady, an essential business book and memoir that comes out March 5. Jessi Roberts is a thought leader, influencer, and risk taker, and Jessi has provided the vision and energy that has inspired the creation of Cheekys. Jessie Roberts joins other leading CEOs and Founders taking part in our Leader Roundtable Interview Series.

Jessi Roberts is the Founder of Cheekys. The DotCom Magazine editorial team has awarded Cheekys  as an Impact Company of 2019, and we are delighted to have Jessi join us for our Leader Round Table Interview. The Cheekys  story is very interesting, and we are very excited to not only interview Jessi, but also put Jessi through our popular speed round as well!

1. Can you describe what the “elevator pitch” for Cheekys is?

Cheekys is a for rural, by rural clothing manufacturer, wholesaler and online retailer based in New Plymouth, Idaho. We make fun, affordable clothing for real women and men living in rural America or who appreciate the rural lifestyle. Are we sassy? You bet.

Cheekys, Rural Clothing Manufacturer
Cheekys, Rural Clothing Manufacturer
2. Many of our readers are just starting to build a company. What advice can you give CEO’s just starting out regarding keeping a company moving forward, and please tell us the key to your company’s success?

It’s not just about out hustling your competition… it’s being willing to do what others aren’t. Even when you think that you can’t, you must still do. Make leadership a lifestyle, not a part-time trait. Teach and train those around you so that you are surrounded by smart and skilled teams because you can not do great things alone. Last but not least by any means, be authentic to your brand. Meet, investigate, discover, and understand your customer by being one of them and a part of their community and life.

3. For other entrepreneurs seeking to build a business as successful as Cheekys, what advice can you give them when times get a little challenging?

It’s not easy to build a multi-million dollar company or everyone would do it. For me, it all comes back to authenticity. What do you value? How do you show up for your customers, employees, and your family? Getting real about what matters is essential if you want to create and live your best life.

4. How important is the commitment to client satisfaction at Cheekys, and how do you make sure your customers will become raving fans of your company?

It’s hugely important to us. We run multiple Facebook groups to connect with our most enthusiastic fans and provide them with products to look and feel their best and a sense of community that can be lacking in rural places. We reach nearly 2 million people a week through social media, and we encourage them to tell us in real time what they are thinking and we can respond. We build real relationships with them, we listen to them, and we value them, and I think that comes through in our sales growth month to month and year over year. Do the work it takes to respond to your customers as a real person. Nothing beats a real conversation.

5. What is the one thing Cheekys does to have great communication with their customers?

Facebook Live has been huge for us. We give our customers a window to our life – warts and all. My kids, husband, staff, and friends all participate. I think people – especially in rural communities – sometimes feel isolated or like their lives are too regular to matter much. We help women especially feel seen in our community and connect with us as well as with one another.

6. In today’s fast changing business environment, what do you do to keep up with the changes? What do you read to stay abreast of things?

I love to read, so that is a long list. I am always encouraging my mentees and employees to educate themselves. There are sooo many free resources out there. Tutorials, websinars, articles… you name it, right at their fingertips. In our office we have a saying “Is this something you can answer yourself?” Not because no one wants to help, because we want to encourage people to learn as they discover the answer. It’s about the journey. I spend at least an hour a day exploring what others do to help Cheekys stay on a level playing field. I would also encourage you to read about the author who wrote what you are reading. Make sure the author is qualified to produce the content they have put out before you take it as the gospel truth.

7. What is your “Why”? Why do you get up in the morning, and how do you keep yourself at peak performance to lead Cheekys ?

I’m really proud that we employ between 20 and 30 people in a town of 1,500. It’s huge to me to be able to help our employees buy their first home, send their kid to college, get out of debt, those sorts of things. We want all of our employees to feel the same sense of ownership that we do with Cheekys. Honestly, my why started out as survival for my family and grew to become providing for others’ families by hiring them and paying a good wage.

8. Can you recommend a book that has had an influence in your career? How did it influence you?

Recently I read Fran Hauser’s Myth of the Nice Girl. Fran was kind enough to endorse my book and we’ve become friends. Like Fran, I’m a big-hearted person but also very direct, so I could relate to her story. Books like this, and I hope mine, are so important for younger women especially as they grow into leaders. Niceness really can be your superpower, so long as you don’t become a pushover or people pleaser.

9. When communicating with your staff at Cheekys, can you tell us the most important thing you do so that they are able to carry out the objectives that you set forth at as the leader?

We always address the elephant in the room. With kindness of course. I work with a lot of women so communication is a top priority. Because texting can be misunderstood, I find the small gesture of a face to face meeting can make a relationship work so much better. A small desk gift, a coffee get-together, a meeting where you listen instead of talk…those things create bonds that texting is unable to accomplish.

10. In one sentence, can you give some advice to fellow entrepreneurs wishing to build a company as exciting as Cheekys?

Prepare to work your ass off, to be authentic, to cry, to laugh and learn how to treat a blister.

Affordable clothing for real women and men living in rural America
Affordable clothing for real women and men living in rural America

We would like to have some fun and do a “First Reaction” round with you!

We will ask you ten more questions that we want you to answer in just one to three words only. Here you go!

1. In three words or less, What makes a successful CEO?
Authenticity, Empathy and Insomnia (just kidding on that last one – I’d sayDrive)

2. Describe Cheekys  in one word?

3. Describe Cheekys customers in one word?
Imperfectly perfect

4. What one attribute do you look for when hiring an employee for Cheekys?
Desires success in life.

5. What is the one word you want your customers to say about Cheekys?

6. In three words or less, describe your passion?
Inspire, Lead, Love

7. In three words or less, describe what it takes to be successful?
Hustle, Heart, Grit

8. In three words or less, describe your first year in business at Cheekys?
Hard AF

9. In three words or less, describe how running a successful company has changed you?
Stronger family life

10. What is the one word that you believe has the most power in the English Language?
No. The power of this word. ?? No, I won’t live that life anymore. No, I won’t be bullied. I won’t be cheated on. No, I won’t work somewhere I hate. No, I won’t be unhealthy or unhappy. No. Take your life and your time into your control. Say no when it’s time. Remember to not only be kind others when saying it but be kind to yourself when you need to use it.

Jessi Roberts , Thank you so much for sitting down with us at our DotCom Magazine Impact Player Round Table. We very much appreciate the time you spent helping others to learn more about what it takes to be a leader. We hope your interview helps our readers, and we wish you, your family, and of course Cheekys , nothing but the best. Thanks again!

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Andy Jacob is Editor In Chief of DotCom Magazine, and an entrepreneur and investor based in The United States. Jacob is the founder and CEO of DotCom Magazine. Andy Jacob is also the Founder and CEO of The Jacob Group, bringing more than 20 years of executive experience founding and leading startups and high growth companies. A Message From Andy Jacob, Editor In Chief, DotCom Magazine: It is my goal to provide you with the most amazing digital marketing value ever offered. I have been told by leading PR experts that an interview in DotCom Magazine may be one of the best investments that a company can make for their brand portfolio. I know how hard it is for great entrepreneurs to get the publicity that they deserve. My passion is helping entrepreneurs, and that’s why I purchased the assets of DotCom Magazine three years ago. My vision was to build a platform to help deserving founders and CEO’s get the attention they deserve. We have put this video interview program together to help our client’s business by providing them the best tool ever to help them land more customers, and increase their revenue. I have been fortunate enough to have been a guest financial expert on CBS, ABC, NBC, Time Warner, and Bloomberg. I have built four multi-million-dollar businesses in my career, and my companies have been covered by The Wall Street Journal and numerous other periodicals. I have been an Ernst and Young Entrepreneur of The Year Award Winner for my leadership in developing and executing corporate strategy and transformational business practices. After 25 years of building successful businesses, DotCom Magazine is my way to give back to deserving Entrepreneurs, Founders and CEO’s. I firmly believe that your interview with DotCom Magazine may be the best value in digital marketing ever offered. That’s why I guarantee it. My team and I look forward to working with you! Andy Jacob, CEO, DotCom Magazine


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