Kierra Henderson is not just driving trucks — she’s driving change, wealth, and legacy. Known across the transportation industry as “The Trucking Guru,” Kierra now owns a fleet of more than 140 trucks and has secured over $100 million in contracted deals, making her one of the most celebrated self-made entrepreneurs in logistics today.
Her success wasn’t handed to her. It was earned through resilience and hustle. Kierra started as a dispatcher, eventually rising to a fleet manager before finding herself out of a job.
Rather than give up, she began dispatching independently from home, leveraging relationships she’d built with owner-operators. That leap of faith became the foundation for her transportation empire.
Over the past 20 years, Kierra has shattered barriers in a male-dominated industry, including winning 45% of contracts in the oil and gas sector — a remarkable feat for any business owner, let alone a Black woman with no formal degree and three children to raise as a single mom.
“I didn’t have a diploma. I didn’t have investors. What I had was drive, experience, and a refusal to fail,” Kierra once shared during a motivational talk.
Kierra’s ambition didn’t stop with building a fleet. Through her exclusive coaching program, “The Truckin’ Millionaires Tour,” she trains aspiring entrepreneurs in freight dispatching, fleet ownership, and freight brokerage. Her goal: to teach others how to build generational wealth through trucking.
Born and raised in Dallas, and the eldest of eight siblings, Kierra credits her father — an entrepreneur himself — for sparking her business mindset. Today, her success has allowed her to retire her parents early and secure her children’s futures, proving that the trucking industry can offer both freedom and fortune.
Students from her course have praised her accessible, no-fluff teaching style and in-depth industry knowledge. One student, Tina Brown, said,
“We were able to get training from one of the best in the industry! Thanks for providing us with the blueprint to dispatching and going hard for the tribe. We’ve learned so much in such a short time!”
Whether you’re behind the wheel or behind a desk, Kierra Henderson is proof that determination, smart strategy, and faith in yourself can lead to extraordinary success — one mile at a time.
For more on Kierra Henderson’s journey or to sign up for her trucking business programs, visit The Trucking Guru’s official site.
