In 1869, when he was only eighteen years old, his father gave him US$12 and asked him to drive five thousand steers to Abilene, Kansas. He sold them for a profit of $55,000. By 1879, he became the manager of the ranch holdings in Wilbarger County, Texas, near China Creek. Upon his father's death in 1902, he inherited landholdings in Wise County and Wilbarger County as well as Clay County, Wichita County, Foard County, Baylor County, Archer County and Knox County. Waggoner also used part of the Big Pasture in Oklahoma, which he leased from Comanche Chief Quanah Parker. In 1905, alongside rancher Samuel Burk Burnett, he went wolf-hunting with President Theodore Roosevelt on the Big Pasture. The two ranchers were hoping to persuade him to keep the land 'open range.' However impressed President Roosevelt was with the adventure, that did not happen. While drilling for water on the Waggoner Ranch, he found oil in 1903. By 1911, he had formed Waggoner Refinery, an oil refinery company for extraction of the oil from his landholdings. As he grew older, Waggoner decided to subdivide his ranch holdings and give a portion to each of his children. Indeed, he wanted them to learn how to take care of the land which would later become theirs. As a result, by 1909, he divided the Waggoner Ranch into four subsections: one for him ; and three smaller 8,500 sub-ranches for his children: Zacaweista, Four Corners, and Santa Ros. However, in 1923, he changed his mind, and set up a Massachusetts trust. His children would elect a Board of Trustees, who would make decisions with him at the helm.
Banking
In 1893, he served as Vice President of the R.C. Neal Banking Company founded by Mr R.C. Neal in Vernon. He served as the founding President of the Waggoner National Bank of Vernon in Vernon from 1899 to 1907. In 1904, he also joined the Board of Directors of the First National Bank of Fort Worth.
Equestrianism
A horsebreeder, he once tried to purchase Man o' War for US$500,000, but the transaction did not go through. However, he purchased other good horses such as Yellow Jacket, Yellow Wolf, Midnight, Blackburn and Pretty Boy. He also built the Arlington Downs located between Fort Worth and Dallas.
Philanthropy
He paid for the construction of three buildings on the campus of Texas Woman's University in Denton. Meanwhile, in 1933, the City of Fort Worth awarded him the honorary title of 'First Citizen of Fort Worth.'
Personal life
He married Ella Waggoner, a younger sister of his stepmother, Sicily Ann Waggoner. They resided at the Waggoner Mansion, also known as 'El Castile', in Decatur, which he restored in 1931. Later, they also resided in Fort Worth. They had two sons and a daughter:
