Small Business Showcase: DeWitt Transportation, LLC

Partnering to Make Long-Haul Transportation Financing Possible

We connected with Oakmont Capital Services’ customer Tim DeWitt of DeWitt Transportation, LLC to learn about his business’ history, the company mission, and his experience working with an independent direct lender.

The Beginning of DeWitt Transportation LLC

DeWitt Transportation LLC was established in August of 2008 when owner Tim DeWitt obtained federal motor carrier operating authority. From its organization date until January 2019, the company consisted solely of its owner driving one truck, pulling step-deck and refrigerated trailers throughout the 48 contiguous United States.

In January 2019, DeWitt decided to expand his business with a fleet of vehicles. He added six trucks in 2019, fourteen in 2020, and 11 to date in 2021, intending to amass 45 trucks by year-end.

DeWitt calls his experience with Oakmont “the easiest commercial equipment financing I’ve procured.”

What Does DeWitt Transportation Do Differently?

DeWitt Transportation offers guaranteed compensation to its drivers, paying a set weekly rate not based on miles or truck revenue. “The goal is to alleviate the stress placed on drivers when they are paid by the mile or percentage of truck gross, which increases driver satisfaction and improves safety,” DeWitt said.

A fleet of DeWitt Transportation branded trucks. DeWitt plans to amass 45 trucks total by the end of 2021.

Despite these accommodating rates, DeWitt acknowledged that this payment method causes challenges when it comes to finding new hires. “The proliferation of trucking companies advertising jobs with obviously inflated pay amounts and/or illegally paying company drivers on a 1099 makes it very difficult for a company paying on a W-2 to get the interest of drivers,” he added.

Even amid these obstacles, DeWitt has built a dedicated team that values his philosophies. He truly views his drivers and office staff as an extended family. “Much as family members depend on each other’s support to succeed in life, we do the same. I depend on all my employees to work hard and make good decisions to keep the company safe and profitable, just as my employees depend on me to make good business decisions to keep the company fiscally sound,” DeWitt noted.

Throughout his career spanning 23 years and over 3.5-million-miles driven, DeWitt felt many, if not most trucking companies he drove for placed little value on the driver. “Misrepresenting earnings potential to attract new hires, then working the driver like a piece of machinery and blaming the driver for anything that goes wrong, seems to be the industry standard,” he said. The philosophy at DeWitt Transportation is different, and the company operates with transparency at all levels to respect and value the contributions of each driver and staff member.

Why Partner with A Commercial Lender?

For many small businesses in the trucking industry, financing is critical to growing a company. “Not many small fleets have $100,000 or more sitting in the bank to pay cash for equipment,” DeWitt remarked. That’s why DeWitt Transportation has partnered with multiple lenders over the years to get to the 32-truck mark. They also have financing locked in for an additional 13 trucks that the company plans to purchase by the end of this year. Oakmont Capital Services is honored to be one of DeWitt’s choices when it comes to equipment financing.

DeWitt has worked closely with Oakmont’s finance professional Jayme Gerads, CLFP, for the past two years. He calls his experience with Oakmont “the easiest commercial equipment financing I’ve procured.”

A green variant of the DeWitt Transportation branded truck.

“Oakmont played a significant role at a critical point in our growth in 2019 and early 2020, both as a direct lender and loan broker,” DeWitt said. “Jayme Gerads of Oakmont was able to find lenders for us to get us over the ten-truck hurdle that is often so hard for small fleets to surpass.”

“I began working with Tim when he first started expanding, so it was neat for me to be part of and witness the rapid growth of his company,” said Gerads. “He taught me a lot about the trucking industry. Personally, it is a great relationship to work with someone who has such deep knowledge about their business. I am thankful to work with Tim and provide equipment financing for his growing company.”

DeWitt Transportation, LLC is a long-haul transportation company headquartered in Marion, Illinois. Since 2008, DeWitt has been transporting step-deck and refrigerated trailers across the 48 contiguous states. DeWitt Transportation provides “power only” services to a single large motor carrier.

Oakmont Capital Services is headquartered in West Chester, PA, with an office in Albany, MN, and is a fast, affordable, reputable solution to equipment financing. Oakmont Capital Services is a direct, independent lender, providing commercial equipment financing and working capital throughout all 50 United States. The professional financing staff at Oakmont has combined experience of over 350 years in the industry and is the reliable choice for today’s financing needs.




Better Rates and Flexible Terms

Oakmont Capital shatters the big bank rates, making us the go-to funding source for a wide range of customers.

Over 20 Years of Experience

Work with our team of experts and grow your business. Speak with our Certified Lease & Finance Professionals today to learn more.

24 Hour Turnaround

Our streamlined application process delivers credit decisions within hours, not days, maximizing your time and experience.