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Home » From Crisis to Opportunity: A Family’s Journey into Trucking Entrepreneurship
Driver Lifestyle & Health

From Crisis to Opportunity: A Family’s Journey into Trucking Entrepreneurship

Trucker Talk RadioBy Trucker Talk RadioDecember 26, 2025No Comments3 Mins Read
From Crisis to Opportunity: A Family's Journey into Trucking Entrepreneurship
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Ashley Stewart: A New Journey as Owner-Operator

COVINGTON, La. — Although Ashley Stewart has never driven a semi-truck, she has traveled a significant distance to become an owner-operator. Earlier this year, she and her husband, DeAntonio Stewart, established their trucking business, Keeping Up with the Stewart’s.

A Nurse Balancing Two Worlds

By profession, Stewart is a registered nurse, juggling her nursing career at Slidell Memorial Hospital in Slidell, Louisiana, and St. Bernard Parish Hospital in Chalmette, Louisiana. With a decade’s experience in emergency medicine, she has encountered numerous challenges. Last fall, an assignment changed the course of her career, both in nursing and entrepreneurship.

A Transformative Travel Assignment

“I took a travel assignment at Baylor Scott & White Health in Dallas for COVID in November and worked there for six months,” she recalled. “Those were tough times with long hours, often reaching 60 hours a week due to staff shortages and a surge in patients.” The demands of her work left little time for her husband and four children, prompting her to consider a future as an owner-operator.

Inspiration and Research

While in Dallas, she spoke with a friend—another nurse who started a trucking company with her husband. Inspired, Stewart began to investigate the trucking industry further. “I started watching numerous YouTube videos about successful trucking businesses, including content from a truck owner known as The Highway Diva,” she said. “I created extensive checklists and made progress step by step.”

Family Involvement in the Business

While Ashley took the lead, her entire family contributed to the venture. From her husband’s driving experience to the company’s name, input was collaborative. “Initially, someone suggested ‘Stewart Trucking,’ but I wanted something unique. My daughter thought of ‘Keeping Up with the Stewart’s,’ inspired by the show ‘Keeping Up with the Kardashians,’” Ashley explained.

The Road to Success

In May, they acquired a 2017 Kenworth T680 in Texas and brought it back to Louisiana. However, the reality of starting a new business hit hard. “We faced challenges in finding partners initially because we were new,” noted Stewart. After some persistence, they finally landed their first load and have experienced success since then.

Managing Two Careers

While DeAntonio handles transportation, Ashley serves as dispatcher and is enrolled in a broker course alongside her nursing job. She believes her nursing background aids her in managing the trucking business: “As a charge nurse, I learned to see the bigger picture, which is valuable in coordinating loads and logistics.” However, balancing both careers and raising four daughters, aged 7 to 14, remains a daily challenge. “I prioritize effectively, sleeping when I can and seizing free moments to research,” she explained.

Embracing Family and Ambition

Stewart emphasizes the importance of teamwork, stating, “My husband and I are in this together. I want our daughters to see that they can achieve anything they aspire to.”

Crisis Entrepreneurship Familys Journey Opportunity trucking
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