Hoiles was born on November 24, 1878 in Alliance, Ohio into a middle-class family. His parents were Samuel Harrison Hoiles, a farmer, and his wife, Ann Ladd Hoiles. The family farm was located on the outskirts of the town, which had 4,000 inhabitants at that time. Hoiles went to a school in town; in his elderliness he remarked that the most important thing he had learned there was "that the State, or a majority of citizens, had the right to use taxation to support the public school system". He once mockingly said of his education that "attending government schools … handicapped me in developing my moral and mental faculties. … In short it retarded my education. "According to Carl Watner, Hoiles learned from his father at the time he graduated from high school that he should "never ask anybody to do something for him that he was not prepared to do himself". He later studied electrical engineering at Mt. Union College in Ohio, where he worked as a subscription solicitor for The Alliance Review, a newspaper edited by his elder brother.

In 1919, shortly after the end of World War I, Hoiles, together with his elder brother, sought to expand their media empire. The first newspaper of which they took possession was Lorain Times Herald, the second was Mansfield News—Hoiles served as publisher for both of them. Believing that what the country needed were newspapers that "believe in moral principles and have enough courage to express these principles", Hoiles, then aged 56, purchased Santa Ana Register, a daily newspaper for the Californian town of Santa Ana.