Tommy Hupp, Estes' Executive Vice President During the Formative Years
Tommy Hupp was a key player in the development of Estes Express Lines. He joined Estes in 1959 and stayed until his 1992 retirement as executive vice president after 33 years of service with the company. He also served on the Estes Board of Directors from 1959 until his death in 2010.
Born in 1923, Henry Thomas Hupp, Jr., grew up in Chase City, Virginia, where company founder W.W. Estes had known his family even before he was born. Tommy recalled that his first unofficial duty with the company—at age 14—was driving a truck down Main Street in Chase City for Mr. Estes. However, a lot happened between that day in 1937 and March 1959, when he officially joined Estes Express Lines.
After graduating from high school, Tommy was accepted to the Virginia Military Institute (VMI), an institution he held dear all of his life. But as with many young men of his generation, his higher education was interrupted by 3 years of service in the U.S. Army during World War II.
After the war, Tommy returned to VMI and finished his degree in civil engineering. Upon graduation in February of 1947, he joined a business with an older VMI alumnus manufacturing Solite building blocks and ready-mixed concrete in Altavista, Virginia.
Shortly after joining Altavista Concrete Products, Tommy married W.W. Estes' oldest daughter, Margaret. He'd known her as his younger sister's friend in school, but the 3-year difference meant that she was only 13 when he left for VMI. However, when he came back from the service, she was 19 to his 22, and that was a whole different story. They began dating that summer, and 2 years later, they married. The couple eventually had two sons, both of whom followed in their father's footsteps by going to VMI and joining Estes. (Billy Hupp is now Estes' executive vice president and COO, and Steve Hupp is corporate secretary.)
Tommy spent 12 years at Altavista Concrete and eventually became co-owner and general manager. But after W.W. Estes had a major heart attack in the mid-1950s, he began the process of persuading Tommy to join Estes Express Lines to work with his son, Robey. In 1959, Tommy finally decided to sell his interest in the business to his partner, move to Richmond and accept a position with Estes.
After W.W. officially hired him, Tommy started handling both the sales and real estate aspects of the company—securing, constructing and relocating terminals, and setting up communications between them. He was quickly promoted to director, and then in 1960, he became treasurer. When he wasn't involved in the company's real estate, he handled Estes' public relations and continued his sales duties. He was also heavily involved in the company's mergers and acquisitions over the years before the industry went through partial deregulation in 1980.
In 1971, Tommy was named executive vice president. He continued to make sales calls on Southside Virginia customers, handle all data communications lines and negotiate real estate purchases and leases for new and existing terminals. By the time he retired in 1992, Estes Express Lines had 42 terminals in 11 states, most of which he had helped purchase, build or lease.
After retirement, he took on an advisory role with the company. And for several years, Tommy traveled with his son, Steve, to new and prospective terminal sites to help him get the lay of the land. Up until his death in September 2010 at age 86, Tommy remained as sharp as ever—he had an amazing memory, he was incredibly detail oriented and he often served as a human Estes encyclopedia.
He also helped provide the perspective needed to learn from the company's past mistakes and build on its successes. During his years at Estes, Tommy witnessed and helped create substantial growth throughout the organization. In 2005, he summed it all up with a remarkable statistic. “Annual volume the first year I was there  was roughly equal to a half a day for Estes now, just under $2 million. It's impressive when you think about the fact that it took us an entire year to do what they're doing now in half a day. But when they get too big for their britches, I remind them of how they got their start.”
First Unofficial Duty
In 2005, Thomas told the story of his first responsibility with the company at the tender age of 14.
“[I] had just gotten my driver's license, and I was walking down Main Street one day when Mr. Estes [W.W.] pulled over to the curb next to me. He said, ‘You got a driver's license yet?' I nodded. He had already built the shop at one end of town, but the terminal hadn't been built down there yet and was still located uptown. He wanted me to drive a truck from the shop back up to the terminal because all his men were out on the road.
“Well, I had never driven a truck, and you had to double clutch back in those days. I just couldn't get the rhythm to save my life. I must have started and stopped that truck five times between the shop and the terminal. I never even got it into second gear.
“Later, when Mr. Estes finally talked me into going to work for him, he made his intentions clear: ‘I want you to understand one thing—I'm not hiring you to drive a truck. I'm hiring you to work in the office.'”
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Company purchases (of other companies or simply lane authority) that Thomas Hupp helped with included:
1967—Four new terminals with the purchase of Carolina-Norfolk Truck Lines
1972—AC Express, Johnson Express purchases for additional territory in North and South Carolina
1975—Pollard Delivery Service authority purchase for territory in Maryland and Washington, DC
1976—Bestway Express purchase to open up rest of South Carolina
1978—The purchase of authority from Palmer Motor Express to serve Savannah, Georgia
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