Retired Air Force man blazes trail beyond trucking dream

Photo/Carly Horton/AJOC

Joseph Tolliver, president/CEO of Trailboss Enterprises Inc., stands in front of a mural depicting various projects his company has going on across the U.S. and in parts of Europe. Anchorage-based Trailboss is the No. 1 transient aircraft maintenance company in the world.
Photo/Carly Horton/AJOC
Joseph Tolliver, president and CEO of Trailboss Enterprises Inc., relies on what he calls the “three Ps” of business: Preparation, perseverance and perspiration. “And it never hurts to pray, either,” he added.

Trailboss has grown over the past 17 years from a one-truck operation to a diverse support services company with contracts all over the U.S. and in parts of Europe.

It wasn’t always easy, and there were setbacks along the way, “but I believe the key resides within,” Tolliver said. “If you have the goals, dreams and aspirations, you can’t be stopped. The greatest impediment lies within.”

Originally from Vicksburg, Miss., Tolliver, a retired chief master sergeant with the U.S. Air Force, arrived in Alaska in 1982. The plan was to work part time, save some money and start a trucking company. Tolliver said he had wanted to start his own trucking company since he was a young airman stationed in Arkansas.

Working in a salvage yard, Tolliver took note of all the trucks driving up and down the highway.

“I started talking to some of the truck drivers, and they told me they were making a pretty substantial amount of money,” Tolliver said. “I thought to myself, ’I could do this.’ And I never lost sight of my dream.”

Tolliver purchased his first truck in 1992, and his company was officially incorporated three years later. Growth was slow but relatively steady, Tolliver said. Trailboss was primarily involved in snow removal work, but in 1996 Tolliver landed his first Small Business Administration 8(a) government contract on Elmendorf Air Force Base. The contract was to provide transient aircraft maintenance work.

Today, Trailboss is the No. 1 TAM company in the world.

Tolliver readily admits his military connections helped him land those first contracts.

“Chief master sergeants are the highest ranking non-commissioned officer in the Air Force,” Tolliver said. “That gives you a lot of influence over things. And those qualities I acquired in the military - communication, leadership and organization skills - have helped me succeed in the business world.”

Trailboss currently provides facility operations and maintenance, logistical support, aviation support services, base operations support, air terminal ground handling services, aerial delivery flight services, construction services and administrative support services.

The company has a diverse customer base, which includes the U.S. Air Force and Army, the Department of Homeland Security and the U.S. Army Corps of Engineers, as well as commercial and prime contractors such as Wal-Mart Stores Inc., the Home Depot Inc. and Alyeska Pipeline Service Co.

Tolliver said he made the decision to move strictly from trucking into government contracting to open more doors for himself and his employees.

“When you’re in trucking, you’re at the bottom of the food chain,” he said. “We’re at the top of the food chain now because we’re a professional contractor. And when you can contract with the federal government, that’s the big daddy rabbit - there’s no one above that.”

Tolliver said his goal over the next five to 10 years is to build Trailboss into a $100 million company.

“I have no doubt we’ll get there,” he said. “That’s just the nature of government contracting.”

But Tolliver is quick to point out his success hasn’t always been effortless.

In 1999, he and his wife purchased a restaurant in Seward. “It seemed like a great business opportunity, but we subsequently learned it was a dream,” he said.

The business lost money, and it almost derailed the entire company. “But we moved on with life and business and persevered,” Tolliver said.

And therein lies the key to success, he said: “At the end of the day, none of us would be successful if we couldn’t reach down and find the courage to prevail. It has become abundantly clear that this is the American dream. To achieve liberty, to participate in a free country - the potential is unlimited.”

As a black businessman, Tolliver said Alaska has provided the most level playing field in terms of race.

“Alaska is truly a melting pot - virtually everyone here came from someplace else,” he said.

Tolliver said he wouldn’t have achieved the success he has without the support of his family. Everything he has, he said, is for them.

“My family can take this business to the next level,” he said. “I do this so they can they can live a full and quality life.”

Carly Horton can be reached at [email protected].

02/23/2008 - 8:00pm