 Liebold attended Detroit's Eastern High School and graduated from Gutchess Metropolitan Business College, and subsequently worked at a number of temporary positions as a stenographer and bookkeeper before being employed by the Peninsula Savings Bank in Highland Park, Michigan.There Liebold rapidly established himself, progressing from messenger to bank officer.His strong financial acumen drew the interest of James Couzens, vice president and general manager of the Ford Motor Company, who asked him to organize the newly established Highland Park State Bank; Liebold started working there as the cashier in 1909, and was later made president of the bank.