At Richard Sears's request, Roebuck took charge of a division that handled watches, jewelry, optical goods, and, later, phonographs, magic lanterns and motion picture machines.

He later organized and financed two companies: a manufacturer and a distributor of motion picture machines and accessories.

After several years in semi-retirement in Florida, the financial losses he suffered in the stock market crash of 1929 forced Roebuck to return to Chicago.

After an enthusiastic public turnout, Roebuck went on tour, appearing at retail stores across the country for the next several years.

[3] They had a son, Alvah Curtis Roebuck, Jr., born 27 April 1914, who also lived in Tujunga, and a daughter, Lucile May Roebuck, born 16 April 1902, who lived in Evanston, Illinois, with her husband Raymond Hiram Keeler.