Raised in Chicago’s East Rogers Park neighborhood by a single mother, Darrell Warren recognized the impact of poverty on his family at a young age. As a youth he got caught up in Chicago street life, which ultimately led to a 12-year prison sentence. During that time, Darrell began planning how he would rebuild his life.
“Everything that I’m doing now with my company…was pretty much a dream, a vision while I was in prison,” he said. “I made up my mind then and there: this doesn’t weigh up for me.”
After his release, Darrell was drawn to the trucking industry due to their lower barriers of employment as well as the potential to make money while seeing the world. However, restrictions from his parole officers prevented him from driving out of state. Darrell needed employment but wanted to avoid complications working for another company, so he decided to take a chance on himself.
In 2022, he started Trina’s Arms Trucking, a transportation solution for brokers, warehouses, distributors, and commercial freight partners throughout the Chicagoland area. The business specializes in less-than-truckload (LTL) and bonded carrier services, which permits Trina’s to carry goods that have yet to clear customs.
At the root of Trina’s Arms Trucking is Darrell’s mother, Trina. Naming the business after her was an easy decision. Throughout his prison sentence, he always felt his mother’s unwavering love and support and honoring her in this way gives him the continued motivation to succeed and the encouragement to never give up.
“If I put one-fourth of the love and support my mom poured into me with any business venture I have, I’m going to be successful,” said Darrell.
But the ride to success hasn’t been straightforward. Renting trucks was costly for Darrell, who knew purchasing his own truck was necessary for growth. However, poor financial advice led him to take on multiple merchant cash advances (MCAs), which are a quick, but very costly way to secure funding. With MCAs, lenders give money up front and take cuts of receipts from the borrower’s bank accounts until the debt is repaid. While this financing is easier to secure than bank loans, MCAs are often given out by predatory lenders and are risky for small business owners. Fortunately, Darrell’s cousin, and now business partner, provided him with a loan that enabled him to pay off his MCAs, clearing the path to financial stability. He now needed funding to keep Trina’s Arms Trucking going.
In 2024, Darrell received an A4CB small business loan which helped him rebuild his business and his personal credit.
“A4CB took a chance on me when my credit didn’t even show,” he shared.
In 2025, Darrell participated in A4CB’s Neighborhood Entrepreneurship Lab (NEL), a 3-month cohort-based accelerator program that pairs community business owners with strategists and advisors who provide intensive support for a business growth initiative. Each entrepreneur also receives a $20,000 grant to help execute their growth plan. Darrell used his funds to purchase two trucks and production equipment.
Following NEL, Darrell needed larger amounts of capital to support his business growth. In 2025, he obtained a revenue-based finance loan from A4CB, which allowed him to hire a financial counselor and purchase marketing equipment.
Today, Darrell leads a team of four and makes it a priority to hire people who were formerly incarcerated, knowing firsthand how difficult it can be to find employment after prison. As Trina’s Arms Trucking continues to grow, building a media presence has become another priority. With his new production equipment, Darrell plans to create content that raises awareness of his business across Chicago. Also important to him is continuing to support others with backgrounds like his own, helping make their road to rebuilding their lives a little easier.
