Working in a Family Business: The Good, The Bad, and The Ugly.

Contributing author, Jewel Jones was raised in the trucking industry. Her father started, Meadow Lark, a freight logistics and trucking company 30 years ago. Today, Jewel’s sister Mandy owns Meadow Lark Logistics and together they founded the first and only work wear clothing line just for truck drivers, Over the Road Apparel. The goal of Over the Road Apparel is to improve the image of the American truck driver and to help drivers everywhere succeed and enhance their careers.

Left: Mandy Roth, Center: Rick Jones, Right: Jewel Jones

Left: Mandy Roth, Center: Rick Jones, Right: Jewel Jones

Working in a Family Business: The Good, The Bad, and The Ugly

I grew up in the trucking industry. My father, Rick Jones, started Meadow Lark, a freight logistics and trucking company in 1983. I went to work there on my summer break from school when I was 14. After high school, I started working full time, just like my older sister, Mandy Roth, did when she graduated high school.

In 2009, I decided that I wanted to forge my own path and follow my dream of working in fashion. I left my hometown of Billings, MT for the bright lights of Los Angeles. It was there that I earned my degree in fashion. It was around the time of my graduation from college that my sister, Mandy, who had purchased Meadow Lark from my father a year earlier, approached me with the idea of a clothing line for truck drivers.

I started researching the idea for her. At the end of my research I determined that there was, in fact, a need for professional, functional apparel made just for the trucking industry. I brought my findings to Mandy and told her that her idea could be something big-something that could help improve the image of the trucking industry and help drivers enhance their careers.

That’s when she offered me the chance of a lifetime: to run a clothing line in the industry that I’d loved my entire life: trucking. Taking the job was a no brainer. All through college, I’d missed the trucking world and this opportunity gave me the chance to work in fashion, as well. My only hesitation centered on whether or not I wanted to work for family again.

Like I said, I’d left Montana and Meadow Lark to forge my own path in the world, and by accepting this once in a lifetime opportunity, I almost felt like I was walking away from that aspiration. To settle my internal dispute over whether or not to return to Meadow Lark, I created a list of pros and cons that essentially became: The Good, The Bad, and The Ugly of working for a family business.


Working with and learning from the people I love.

My family are best friends. Not only do I get to work with them, I get to learn from their years of experience in trucking and in business. There have been situations in the course of launching OTR Apparel where I was unsure of the best course of action. Instead of being insecure about asking for help, I turned to my parents or my sisters for advice on how to move forward. Knowing that they will give me the guidance I need, free of judgment, is about as good as it gets.

Carrying on the family legacy.

My father and mother worked so hard to build their company with integrity. They treated the business, and everyone involved with it, as part of our family. They weathered industry ups and downs, recessions, and every other challenge that a business could face. Nothing makes me prouder than walking through the halls of Meadow Lark. It is my parent’s legacy that my sister is now carrying on, and I’m honored to be a part of it, and to have the opportunity to contribute to it in my own ways. 


People assuming I obtained my position through nepotism and not talent and ability.

This one used to bother me a lot. For the last few years, it hasn’t crossed my mind once. I used to think I had something to prove. I felt as though I had to show people I earned my career and that it wasn’t handed to me. I’m sure there are people that think nepotism got me here, and maybe it did. But I look back on all of the hard work I put into getting OTR to where it is today, and find myself not caring about this one anymore. If you work in a family business and worry about this particular ‘bad’, just know that the only thing that matters is how hard you work for your success and not how people assume you got it.

The strain that working together puts on family relationships.

It is no secret that working with family can destroy relationships. It’s not easy when one family member is in charge of managing another, and it’s just as difficult when family members have to manage a business together. Working together has destroyed countless families. Sometimes it’s hard to turn off the business side of your relationships and just be family. Somehow, my parents, my sister, and I have achieved this. I think the key to maintaining healthy business/family relationships is to compartmentalize when you are ‘all business’ and when you are ‘all family’. Sometimes you have to just turn off ‘business mode’ and be together.

Left: Mandy, Right: Me

Left: Mandy, Right: Me


Always being seen as the little sister.

This one is really personal and that makes it ugly. Because jealousy and feeling overshadowed look ugly on everyone, especially me. Not to mention that being back in the family business meant that I would always be introduced as the little sister. It also meant that I would always feel like the little sister as long as I was there. And make no mistake, any negative connotation to being the little sister in this family business, I earned on my own. I wondered if I could really start over there now that I was educated and older than I was when I left. I thought long and hard about what it'd be like being the little sister again, and the more I thought about those words, the more they began to mean to me. Ultimately, I decided that being a little sister was a GREAT thing, and when it came down to it, I was PROUD to be the little sister.

  • I’m the little sister in a family grown from the trucking industry.
  • I’m the little sister of a CEO who loves her company and employees as though they were her own family.
  • I’m the little sister who gets to live her dream of working with her family in fashion and in trucking.

In the end, there was no way I could have walked away from the opportunity Mandy was offering. I loved trucking too much, I loved my family too much, and I loved the idea that through my passion for fashion, I could make a difference in the lives of countless drivers.