Cole was appointed as a director of the
Nashville, Chattanooga and St. Louis Railway at the age of 26, in 1900. In 1921–1922, when his railroad workers went on strike after their wages were lowered by 12 percent by the
U.S. Railway Labor Board, Cole threatened them with dismissal and loss of their pensions. In retaliation, strikers went to his house on West End Avenue, and they "bombarded [it] with bottles until its concrete porch was littered with glass". Cole resigned in 1926. Cole was the president of the
Louisville and Nashville Railroad from 1926 to 1934. At the time of his appointment,
B. C. Forbes, the founder of
Forbes magazine, noted that it was unusual for a man of privileged upbringing to become the president of a railroad company. As it was the
Great Depression, Cole lowered his workers' wages and took a pay cut. ==Civic activities and politics==