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

ACLU By ACLUSponsored

Over the past four years, we grew accustomed to a regular barrage of blatant, segregationist-style racism from the White House. Donald Trump tweeted that “the Squad," four Democratic Congresswomen who are Black, Latinx, and South Asian, should “go back" to the “corrupt" countries they came from; that same year, he called Elizabeth Warren “Pocahontas," mocking her belief that she might be descended from Native American ancestors.

But as outrageous as the racist comments Trump regularly spewed were, the racially unjust governmental actions his administration took and, in the case of COVID-19, didn't take, impacted millions more — especially Black and Brown people.

To begin to heal and move toward real racial justice, we must address not only the harms of the past four years, but also the harms tracing back to this country's origins. Racism has played an active role in the creation of our systems of education, health care, ownership, and employment, and virtually every other facet of life since this nation's founding.

Our history has shown us that it's not enough to take racist policies off the books if we are going to achieve true justice. Those past policies have structured our society and created deeply-rooted patterns and practices that can only be disrupted and reformed with new policies of similar strength and efficacy. In short, a systemic problem requires a systemic solution. To combat systemic racism, we must pursue systemic equality.

What is Systemic Racism?

A system is a collection of elements that are organized for a common purpose. Racism in America is a system that combines economic, political, and social components. That system specifically disempowers and disenfranchises Black people, while maintaining and expanding implicit and explicit advantages for white people, leading to better opportunities in jobs, education, and housing, and discrimination in the criminal legal system. For example, the country's voting systems empower white voters at the expense of voters of color, resulting in an unequal system of governance in which those communities have little voice and representation, even in policies that directly impact them.

Systemic Equality is a Systemic Solution

In the years ahead, the ACLU will pursue administrative and legislative campaigns targeting the Biden-Harris administration and Congress. We will leverage legal advocacy to dismantle systemic barriers, and will work with our affiliates to change policies nearer to the communities most harmed by these legacies. The goal is to build a nation where every person can achieve their highest potential, unhampered by structural and institutional racism.

To begin, in 2021, we believe the Biden administration and Congress should take the following crucial steps to advance systemic equality:

Voting Rights

The administration must issue an executive order creating a Justice Department lead staff position on voting rights violations in every U.S. Attorney office. We are seeing a flood of unlawful restrictions on voting across the country, and at every level of state and local government. This nationwide problem requires nationwide investigatory and enforcement resources. Even if it requires new training and approval protocols, a new voting rights enforcement program with the participation of all 93 U.S. Attorney offices is the best way to help ensure nationwide enforcement of voting rights laws.

These assistant U.S. attorneys should begin by ensuring that every American in the custody of the Bureau of Prisons who is eligible to vote can vote, and monitor the Census and redistricting process to fight the dilution of voting power in communities of color.

We are also calling on Congress to pass the John Lewis Voting Rights Advancement Act to finally create a fair and equal national voting system, the cause for which John Lewis devoted his life.

Student Debt

Black borrowers pay more than other students for the same degrees, and graduate with an average of $7,400 more in debt than their white peers. In the years following graduation, the debt gap more than triples. Nearly half of Black borrowers will default within 12 years. In other words, for Black Americans, the American dream costs more. Last week, Majority Leader Chuck Schumer and Sen. Elizabeth Warren, along with House Reps. Ayanna Pressley, Maxine Waters, and others, called on President Biden to cancel up to $50,000 in federal student loan debt per borrower.

We couldn't agree more. By forgiving $50,000 of student debt, President Biden can unleash pent up economic potential in Black communities, while relieving them of a burden that forestalls so many hopes and dreams. Black women in particular will benefit from this executive action, as they are proportionately the most indebted group of all Americans.

Postal Banking

In both low and high income majority-Black communities, traditional bank branches are 50 percent more likely to close than in white communities. The result is that nearly 50 percent of Black Americans are unbanked or underbanked, and many pay more than $2,000 in fees associated with subprime financial institutions. Over their lifetime, those fees can add up to as much as two years of annual income for the average Black family.

The U.S. Postal Service can and should meet this crisis by providing competitive, low-cost financial services to help advance economic equality. We call on President Biden to appoint new members to the Postal Board of Governors so that the Post Office can do the work of providing essential services to every American.

Fair Housing

Across the country, millions of people are living in communities of concentrated poverty, including 26 percent of all Black children. The Biden administration should again implement the 2015 Affirmatively Furthering Fair Housing rule, which required localities that receive federal funds for housing to investigate and address barriers to fair housing and patterns or practices that promote bias. In 1980, the average Black person lived in a neighborhood that was 62 percent Black and 31 percent white. By 2010, the average Black person's neighborhood was 48 percent Black and 34 percent white. Reinstating the Obama-era Fair Housing Rule will combat this ongoing segregation and set us on a path to true integration.

Congress should also pass the American Housing and Economic Mobility Act, or a similar measure, to finally redress the legacy of redlining and break down the walls of segregation once and for all.

Broadband Access

To realize broadband's potential to benefit our democracy and connect us to one another, all people in the United States must have equal access and broadband must be made affordable for the most vulnerable. Yet today, 15 percent of American households with school-age children do not have subscriptions to any form of broadband, including one-quarter of Black households (an additional 23 percent of African Americans are “smartphone-only" internet users, meaning they lack traditional home broadband service but do own a smartphone, which is insufficient to attend class, do homework, or apply for a job). The Biden administration, Federal Communications Commission, and Congress must develop and implement plans to increase funding for broadband to expand universal access.

Enhanced, Refundable Child Tax Credits

The United States faces a crisis of child poverty. Seventeen percent of all American children are impoverished — a rate higher than not just peer nations like Canada and the U.K., but Mexico and Russia as well. Currently, more than 50 percent of Black and Latinx children in the U.S. do not qualify for the full benefit, compared to 23 percent of white children, and nearly one in five Black children do not receive any credit at all.

To combat this crisis, President Biden and Congress should enhance the child tax credit and make it fully refundable. If we enhance the child tax credit, we can cut child poverty by 40 percent and instantly lift over 50 percent of Black children out of poverty.


We cannot repair harms that we have not fully diagnosed. We must commit to a thorough examination of the impact of the legacy of chattel slavery on racial inequality today. In 2021, Congress must pass H.R. 40, which would establish a commission to study reparations and make recommendations for Black Americans.

The Long View

For the past century, the ACLU has fought for racial justice in legislatures and in courts, including through several landmark Supreme Court cases. While the court has not always ruled in favor of racial justice, incremental wins throughout history have helped to chip away at different forms of racism such as school segregation ( Brown v. Board), racial bias in the criminal legal system (Powell v. Alabama, i.e. the Scottsboro Boys), and marriage inequality (Loving v. Virginia). While these landmark victories initiated necessary reforms, they were only a starting point.

Systemic racism continues to pervade the lives of Black people through voter suppression, lack of financial services, housing discrimination, and other areas. More than anything, doing this work has taught the ACLU that we must fight on every front in order to overcome our country's legacies of racism. That is what our Systemic Equality agenda is all about.

In the weeks ahead, we will both expand on our views of why these campaigns are crucial to systemic equality and signal the path this country must take. We will also dive into our work to build organizing, advocacy, and legal power in the South — a region with a unique history of racial oppression and violence alongside a rich history of antiracist organizing and advocacy. We are committed to four principles throughout this campaign: reconciliation, access, prosperity, and empowerment. We hope that our actions can meet our ambition to, as Dr. King said, lead this nation to live out the true meaning of its creed.

What you can do:
Take the pledge: Systemic Equality Agenda
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Featured image by Shutterstock

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