He was apprenticed to a printer, and had experience in England, Scotland, Ireland and New York before emigrating to South Australia on the steamer "John Elder" in 1884.
[1] He worked on David Drysdale's Port Augusta Dispatch, and ran a newspaper in Teetulpa before founding The Petersburg Times, Orroroo Chronicle and Northern Advertiser in 1887.
In 1896 his brother Samuel W. Osborne came out from England to assist him, and together they founded the Quorn Mercury and the Advertiser in Port Pirie, where he remained for many years.
In 1897 Robert left Petersburg to establish a printing business in Victoria Square, Adelaide, later moving to Currie Street.
He married Laura Martha Axford, (c. 1861 – 16 April 1928) on 26 January 1887; their children included Mrs. L. F. Sutherland, of Sydney, and Miss Dorothy Osborne, of Launceston.