A prison pamphlet containing simple arithmetic — four cars on a trailer, $250 a car, $1,000 a day — set Debon 'DJ' Sims on a path to building a trucking business that he says nobody could take from him, according to a report by FreightWaves. That decision, made in a cell in 2015, led to a CDL, a lease-purchase truck, and eventually his own fleet and brokerage.
The Pamphlet That Changed Everything
In 2015, Sims got into what he calls the only trouble he had ever been in, his first time, and ended up in prison. There, a man handed him a pamphlet that broke down the economics of car hauling. Sims did the math repeatedly: $250 per car, four cars per trailer, $1,000 a day, $2,000 in two days. 'This is where I’m going to change my life at,' he remembered thinking, according to FreightWaves. He started studying toward his commercial driver’s license (CDL) while still incarcerated.
He came home in April 2018, started CDL school that November, had his license by December, and flew out for his first job on Christmas Day. He never ended up hauling cars; instead, he climbed into a semi and fell in love with driving and being his own boss.
Learning the Numbers
Without money for a truck, Sims entered lease-purchase programs, first with Trans Am and later with Hirschbach. He is careful about how he talks about lease-purchases, knowing many drivers fail. But he came out with his numbers. A brother who had been driving while Sims was locked up trained him on fueling, running his clock, and operating as his own boss. Sims paid attention to every dollar. The weekly truck payment came out every Thursday to Wednesday: $1,300 to $1,500 before fuel, before maintenance. He learned the brutal rhythm: miss too many days and you go negative, nearly impossible to climb back out.
Sims never went negative — not once across two lease-purchase programs, FreightWaves reported. He was praying out loud to make it to the next station when his tank hit empty, but he knew his numbers cold. In 2019, he bought his own truck, eliminating that $1,300–$1,500 weekly payment. He calls it a step up, but admits he wished he had understood maintenance costs before jumping.
'This is where I’m going to change my life at.' — Debon Sims, reflecting on the prison pamphlet
The Amazon Lesson
Early on, Sims landed an Amazon contract. But it ended, teaching him not to depend on any single customer. He rebounded by using load boards and eventually secured a dedicated deal. The loss of the Amazon contract reinforced the need to build a diversified book of business.
Building Authority
Through relentless dedication, Sims built a company that now owns multiple trucks and operates a brokerage. His why never wavered: he refused to go back to prison. 'That’s what pushes me every day,' he said. 'I don’t want to go back. I’m not going back.' His story highlights the importance of financial discipline, understanding costs, and building relationships in the trucking industry.
For logistics professionals, Sims’ journey underscores the challenges of lease-purchase programs and the rewards of ownership. His ability to avoid negative equity in lease-purchase and recover from a lost contract offers practical lessons in resilience.
Watch List
Sims continues to grow his fleet and brokerage. Factors to watch include his ability to maintain a diversified customer base, manage rising maintenance costs, and navigate the evolving freight market. His story serves as a case study for addressing driver retention and entrepreneurship in trucking.
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