Juhan (John) Pihooja was born in 1892 to Peeter and Liiso Pihooja, both of Voru, Estonia. John was the youngest son in a family of six boys and two girls. Upon their 21st birthday, the Pihooja boys were obligated to serve time in the Russian army. In 1905 John's older brother, August, emigrated to Canada with is wife and infant daughter to join their friend Henry Kingsep, who owned a homestead west of Red Deer.
In 1912, 19-year-old John and his older brother Karl arrived in the Gilby-Medicine River area of Alberta where their brother August was farming. John soon found work at a nearby sawmill and continually exchanged postcards with his family back in Estonia. John briefly resided in the Gastown district of Vancouver working in the logging industry. By 1916, John and Karl left for Anaconda, Montana to begin work in a copper smelter. Enjoying their bachelor lifestyle, John and Karl worked hard and maintained a lively social life filled with dancing and fraternizing with the locals. After returning to Red Deer for a short stint, John met Karl in Seattle to embark on a world tour. Some of the places they visited include Finland, Siberia, Hong Kong and Shanghai. John and Karl returned to Estonia in 1922.