As a young boy, Hilton developed entrepreneurial skills working at his father's general store in Socorro County, New Mexico. This was followed by varied experiences, including a stint as a representative in New Mexico's first State Legislature and a career decision to become a banker.
It was with the intention of buying a bank that he arrived in Texas at the height of the oil boom. He bought his first hotel instead, the 40-room Mobley Hotel in Cisco, Texas, in 1919, when a bank purchase fell through. The hotel did such brisk business that rooms changed hands as much as three times a day, and the dining room was converted into additional rooms to meet the demand.