Financing Helps a Trucking Company Grow in Many Directions

Jason DeSanto, Madison Capital testimonial story

Jason DeSanto, Owner, Windy City Jay Truck Sales

Jason DeSanto entered the trucking industry in 1993 when he followed a friend to Ryder Transportation Services. He spent the next 16 years gaining broad experience before opening his first business, WindyCityJay Truck Sales, in Bolingbrook, Illinois. Today this dealership specializing in high-quality, used commercial trucks is just one of half a dozen transportation companies owned by DeSanto—and more may yet develop as DeSanto continues teaming his great ideas with financing from Madison Capital.

“This business gets in your blood and it stays there,” says DeSanto. “It’s exciting, even though it has its ups and downs, and it’s one of those great industries where you learn something every day.”

DeSanto found Madison Capital through a friend about four years ago and says the finance company “has the personal touch. “They’re one phone call away, and they can usually get a deal done for me in a day or two,” he says. “They fill a nice niche for companies with good credit who want a financing source in addition to their bank.”

From the start, DeSanto developed quality relationships with customers, and this way of operating continues. Deepening relationships with Windy City Jay customers led DeSanto to establish two leasing companies: Lake Ridge Financial, which leases “mostly trucks,” says DeSanto, and BL Equipment Finance, which leases mostly trailers. Both businesses lease directly to customers and rely on financing supplied by Madison Capital.

Once the leasing companies were up and running, DeSanto acquired Capitol Trucking, a local and regional hauler handling over-the-road and intermodal freight for paper companies, manufacturers and other large commercial enterprises. He also formed Merging Express LLC as the holding company overseeing all trucking operations. Through it all, DeSanto worked with Madison Capital, which supplied financing, business consulting and overall support.

“Madison Capital has helped me grow both my trucking and leasing businesses,” says DeSanto. “They react quickly, their rates are fair, and their service is impeccable. I’ve dealt with Madison Capital for years now and feel very close to them. And I get the same great service now that I received back then.”

Most recently, DeSanto signed an agreement with Montana-based Meadow Lark Companies to act as exclusive shipping agent within 100 miles of Chicago. Says DeSanto of Meadow Lark, “We’re both striving for the same thing: happy drivers, happy employees and a profitable company while still keeping a family atmosphere. We’re off to a good start.”

Asked how he manages so much business spread across several companies, DeSanto offered this nugget: “You have to be able to delegate. There are so many aspects to trucking, from safety to recruiting to financing, and you can’t watch everything yourself. You have to find others who are honest and true professionals to share the load. For me, Madison Capital is one of those.”