This Woman Made Millions In Trucking And Is Teaching Others How They Can, Too

Breaking into a male-dominated field led Casey Cooper to the business—and life—of her dreams.


When you think of a trucker, the image of a beautiful, skinny-jeans-wearing, caramel-skinned woman behind the wheel is probably not what comes to mind. Indeed, the $791 billion industry is dominated by male drivers, many of which are over age 55 and white. But Casey Cooper is helping to change that, one million-dollar contract and one woman at at time. She is among the growing number of women in the industry, and among the few Black female millionaires who owns a company that continues to thrive.

The Virginia Beach, Va. native, and founder and president of The Compass Circle definitely knows what it's like being a boss in a male-dominated industry who built her business from the ground up. And the idea for the business, according to Casey, was sparked from sheer vision and abrupt inspiration. "One day I literally woke up, and I was like, 'You know what? I think I'm going to buy a truck.' And I couldn't tell you where the idea came from. Nobody in my family was in trucking. I just literally woke up one day and said, 'I'm going to do this.'"

Image courtesy of The Compass Circle

When Casey started in the industry, she liked the idea of employing others to drive, but she ended up having to learn how to drive for herself. "My priority at the time was to figure out how I was going to finance the first vehicle. I was 25 when I started, so I didn't have a lot of credit and I didn't have a whole lot of money." Her first investment was in an $80,000 dump truck. "Luckily my mom was able to co-sign for me, but that was only the first challenge. The second challenge was the down payment [which was] $2,500 back then, and I had a fiance at the time who helped me with the funds."

Casey also faced a third major hardship simply not seeing many people who looked like her doing what she was attempting to do.

"Trucking wasn't popular for women at the time, so I didn't have any point of reference. I was like a fish out of water."

To further turn her idea into reality, she began researching the credentials needed to drive and studying a free manual from the Virginia DMV. She took the commercial license permit test and passed, but when she asked a few mechanics she knew to help her with driving experience, they didn't take her serious. "They laughed me off the lot, like 'Girl, you're not going to be able to drive!'

She eventually found drivers who she'd pay to ride with her every day. "I knew I could still make money while getting the feel of everything. I thought it was best to learn how to drive first because in the future, if somebody's truck broke down, a driver quit, or even if we needed to take the truck around the corner to the shop, somebody needed to be able to be able to drive. Thank God I had the presence of mind to at least go through that driving process early on."

Image Courtesy of The Compass Circle

The more money Casey made taking on hauling projects, the more she'd invest back into her business, and she was able to expand her truck fleet and work with more drivers. She'd research more about ways to expand her clientele and make more money, and she later found out that the major profits were made via federal contracts. "Initially, I didn't know what I was doing in terms of the process of going for those contracts, but it was through those contracts I was really able to scale my business. I ended up just applying. I know there are a lot of myths related to that, and true, [getting federal contracts] happens so many different ways for different people."

For her, the success was seamless once she learned about the proper paperwork and other important protocols. After her initial three government-funded projects, she was able to earn $6 million in profits.

"For anybody who is looking for longevity in the business or to get your feet under you financially, try the federal sector. And it doesn't have to be huge multi-million-dollar contracts. In fact, the profit margins on smaller contracts are a lot greater than on the larger ones."

Trucking isn't limited in terms of the types of businesses you support or the types of hauls you transport, Casey added. It could be anything from construction materials, to retail goods, to farming materials and animals. No matter what the haul, she's a huge advocate of getting your business certified. "Getting the woman-owned certification is how I got my very first contract, and I had another certification that allowed me to get my first million-dollar project."

Casey's company is also part of the 8(a) program which levels the playing field for disadvantaged small businesses to have the opportunity to take on federally backed projects, providing a fair chance for women and minorities.

Today, her days driving have been replaced with managing a network of drivers, traveling to conferences, hosting events, and meeting with clients who either want to get into the trucking industry or who are already in and want to take their careers or businesses to the next level. She's now built a business where she can earn passive income, and she's cultivated a following of more than 270,000 on Instagram alone. She conducts global events to teach budding entrepreneurs as well as industry veterans about how to level up and reach the seven- and eight-figure mark. She even has an extension of her brand in the works that she said will be "the Uber of trucking."

"Being creative and coming up with new projects, new incentives, new concepts—I just love using that, combined with my background in project management, to help my clients bypass the challenges that I've gone through."

As a divorced mother of two, Casey has now developed a sense of pride in the financial and time freedom, luxury lifestyle, and redefinition of what success and motherhood looks like after launching a successful business. She's relocated to Miami, enjoys yachting, and travels the world both for business and for pleasure.

"A lot of times people are like, 'Oh she's just a pretty face,' but when I open my mouth, I can't fake about the information that comes out. You can't fake knowing about these certifications. You can't fake this stuff. It's a chance to dispel those myths. I didn't have some NFL boyfriend or a rich dad to put me in position. I really got this out of the mud. Being able to show up, present, as I am, I bring all my gifts with me. I like to really show people that I'm not some cute girl. I really can stand toe-to-toe and talk this talk and walk it."

For more about Casey Cooper, The Compass Circle, and her programs on trucking entrepreneurship, visit her website or follow her on Instagram @TheCompassCircle.

Featured image courtesy of The Compass Circle

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