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Woodson spent his entire business life in Cheyenne, except for four years at the University of Denver and military service from 1943-1945. Woodson started his business career working with his father during the late 1940s at Capital Coal Company. When natural gas became the fuel of preference, the Woodsons closed their coal company and purchased an ice company. Ironically, the land the ice company sat on is now the current location of the Taco John’s International, Inc. headquarters.
From coal and ice, Woodson expanded his business interests in the 1950s to include Woodson Realty, Eberly-Woodson Insurance, and Checker Yellow Cab. It was through his real estate business that Woodson was introduced to John Turner, who was looking for land on which to put his “Taco House,” as he called it. When Turner wanted to build another Taco House just six days prior to Cheyenne Frontier Days, Holmes—who had his own business, Holmes Camper and Equipment—stepped in and built a prefabricated Taco House in downtown Cheyenne, where a Taco John’s still stands today.
At the time Woodson said, “It wasn't much of a building, only 360 square feet with red metal siding and yellow stripes, quite gaudy. A sign on the front of it had a devil, with the words ‘The Hottest Spot In Town.’"
The hottest spot in town soon became the offices of Woodson-Holmes Enterprises, which acquired the franchise rights to the Taco House concept in 1969. Believing the concept would work in other cities in the region, Holmes and Woodson changed the name to Taco John’s and immediately began franchising restaurants based on the Taco House concept. They left many elements the same, including much of the menu and the special seasonings developed by Turner. They opened their first franchised stores in Rapid City, South Dakota; Scottsbluff, Nebraska; and Torrington, Wyoming. Like the first Taco House, the new Taco John's outlets were a big success. Holmes and Woodson knew that they were onto something. During the 1970s, they expanded throughout the upper Midwest and West, franchising Taco John's outlets primarily in small towns. As Holmes was quoted in 1977 in the Wyoming Tribune, “When Jim and I joined John Turner in this venture a few years ago, we had no idea that the Taco John’s franchise would come this far, this fast.”
The decision to target small towns was a strategy that became characteristic of the Taco John's organization. Franchising was a relatively new concept at the time, and most other restaurant chains focused on opening franchise outlets in larger urban areas. In contrast, Woodson and Holmes decided to concentrate in non-urban areas where competition was less intense. Their goal was to bring to those towns a unique eating experience, including great-tasting Mexican food, served fast, at reasonable prices. The overall strategy was ultimately a big success. Each Taco John's restaurant developed a loyal customer base in its town, and also managed to attract regular patrons from outlying regions with its unique, craveable flavors.
In 2009, Taco John’s will celebrate 40 years of bringing Mexican food to the small towns and cities that welcomed the restaurants from the start.
Barry Sims, Taco John’s President and CEO said, “Jim was one of the most respected people I’ve ever known. He was a caring mentor for so many of our employees and franchise owners; he truly loved everything about the Taco John’s business. His compassion for each of our franchisees was genuine. Over the years, everyone associated with Taco John’s became one big extended family, with Jim and Harold as patriarchs. His leadership, friendship, wisdom and guiding hand will be deeply missed.”