The younger Cheney prepared for college at English High School in Boston and with a private tutor.

Until the death of his father in 1895 Cheney aided him in the management of his interests, which included the largest portfolio of railroad securities held in the Boston area.

He also served as president of the San Diego Land & Town Company, one of his father's old ventures.

[2] He was married at Covington, Kentucky, on February 23, 1898, to Julia Arthur (née Ida Lewis), a noted actress.

Cheney later suffered heavy financial reverses, and during the last years of his life he was no longer active in business.