In 1883, he relocated to the state capital of Austin. He organized and served as president of the American National Bank from 1890 until 1919. The bank commonly paid an annual dividend of 20 percent to its shareholders. The Littlefield Building on Congress Avenue in downtown Austin now houses Capital One Bank. From 1895 to 1903, Littlefield owned the Driskill Hotel, located near the Littlefield Building. He installed the first electric lighting system in the hotel, which became a gathering place for Texas politicians during much of the 20th century.