Pandemic leads family down unique path to trucking entrepreneurship

COVINGTON, La. — While Ashley Stewart has never sat behind the wheel of a semi, she has sure covered a lot of miles to become an owner-operator. She and her husband, DeAntonio Stewart, launched their trucking company, Keeping Up with the Stewart’s, earlier this year.

Stewart, who’s a registered nurse by trade, has balanced the new venture with her double-duty work at Slidell Memorial Hospital in Slidell, Louisiana, and St. Bernard Parish Hospital in Chalmette, Louisiana. During 10 years of working in emergency rooms, she’s seen a little bit of everything and anything that could possibly walk through the door.

But last fall, she took an assignment that altered her career, both as a nurse and as a budding entrepreneur.

“I took a travel assignment at Baylor Scott & White Health in Dallas for COVID in November. I did that for six months,” she said. “That was hard. Long hours. We had to do 60 hours a week back when COVID was still very rampant. So, they were short-staffed, and we had a lot of patients. It took a toll.”

Between the hectic schedule and crushing demands of the assignment, Stewart had precious few opportunities during that time to see her husband and four children. Thinking of them and their futures, she began to “percolate” the idea to become an owner-operator.

“I was talking to one of my friends out there, another nurse. She actually formed a company with her husband. And then there’s a group that I’m part of on Facebook where there’s a woman who actually used to be a nurse, and she did the same thing. And she’s had a very successful trucking business career,” Steward explained. “I had a lot of time to think during that assignment. I began to wonder, what all goes into it?”

Stewart floated the idea to her husband, who’d driven with local trucking companies for some time. With him on board, she began researching the ins and outs of starting up the business.

“I mentioned the idea around February, and I just kinda kept working toward it,” she said. “I watched YouTube video after YouTube video all about successful trucking companies. I watched The Highway Diva; she’s a truck owner and she makes multiple YouTube videos. She’s extremely helpful. She drives with her daughter sometimes. I commented on it, and she commented back to me. She’s just great. She’s very friendly.

“I made a big ol’ check list, and I would take notepads and I would just literally make lists and I’d write notes. And as I went, I would just scratch it off. I did the LLC and applied for our own vehicle authority. I just did it step by step,” she continued. “That’s what I’d tell anyone who wants to do this. I would say, ‘Take baby steps and research and make lists. Just take your time.’”

Stewart is quick to point out that while she was spearheading the effort, the entire family had input at some level, from her husband’s experience behind the wheel to settling on the name of the venture.

“At first someone said, ‘Stewart Trucking’ and I thought, ‘No, I want it to be cute. Stand out,’” she said.

“One of my daughters actually came up with the name, ‘Keeping Up with the Stewart’s’ which is like ‘Keeping Up with the Kardashians,’ you know. She always says she wants a TV show,” Stewart said. “So, I was sitting there one day at work, and I was like ‘You know what? That could work. ’Cause it’s a trucking company and it’s always moving.’”

In May, the family found the perfect rig — a 2017 Kenworth T680 — in Texas and drove it home to Louisiana after Ashley’s stint in Dallas wrapped up. Once settled into the new routine, the challenging realities of making a go in the trucking business sank in.

“At first, we were very defeated because nobody would work with us because we were so new,” Stewart said. “I had been working on it since March but because it just went active, it finally cleared May 28, that’s what they were going by. The first week, we’d make a call they would say ‘Nope. Nope. Nope.’”

Their break finally came, however, and Keeping Up with the Stewart’s was on the road.

“We did one load, like a trailer drop — that was our first move — and ever since that, we’ve been successful,” she said.

While DeAntonio hauls the dry vans to various destinations out of state, Ashley serves as dispatcher and is taking a broker course, in addition to continuing her nursing career. She said her experience as a nurse actually plays a role in her life as an owner-operator.

“It’s funny,” she said. “When you’re looking at the loads and trying to piece and part them together and map load after load, you have to see the bigger picture. As a charge nurse and a house supervisor, you have always look at the bigger picture too, like the flow and the management of things. Learning the trucking business, I can really rely on how I manage others as a nurse, seeing a bigger picture.”

Still, she admits balancing two careers and a family of four daughters, ranging in age from 7 to 14, is not without its daily challenges.

“It’s hard some days, but I think being a nurse through COVID, you learn how to prioritize a lot of things — what is a priority in life and what isn’t, you know?” she said. “I sleep when I can and research some stuff when I have a little free time here and there and just keep working hard.”

One of the most important things is to not go it alone, she said.

“My husband and I work on this together,” she explained. “I just wanted to have something we could call our own. I would want my daughters to see that and know that whatever you put your mind to, the sky’s the limit.”

Dwain Hebda

Dwain Hebda is a freelance journalist, author, editor and storyteller in Little Rock, Arkansas. In addition to The Trucker, his work appears in more than 35 publications across multiple states each year. Hebda’s writing has been awarded by the Society of Professional Journalists and a Finalist in Best Of Arkansas rankings by AY Magazine. He is president of Ya!Mule Wordsmiths, which provides editorial services to publications and companies.