Born in 1884 to a Jewish family in Irkutsk, Russia, Gershkovitch grew up listening to chamber music and was sent to Saint Petersburg in his late teens to study at the Imperial Conservatory. Gershkovitch arrived with "17 rubles in his pocket and his flute under his arm"; he auditioned and was awarded a scholarship. At the Conservatory, he learned from respected Russian composers such as Alexander Glazunov, Nikolai Rimsky-Korsakov and Nikolai Tcherepnin, and completed coursework in opera and ballet production. In 1913, he graduated with honors in flute and conducting, and was awarded the Schubert Scholarship for a year of study under German conductor Arthur Nikisch in Berlin. However, World War I forced Gershkovitch to return to Irkutsk and enlist in the military. Gershkovitch began his conducting career as head of the Imperial Russian Army's military symphony orchestra, a position he held through the 1917 revolution. In 1918, Gershkovitch married in Irkutsk and established a successful fine arts conservatory and symphony orchestra, which continued under the Bolshevik regime. Gershkovitch and his wife left Russia in 1921 for China, where they befriended composer Aaron Avshalomov. Ballerina Anna Pavlova offered Gershkovitch an assistant conductor position with her orchestra, which was touring throughout the Orient. Gershkovitch settled in Tokyo to lead the newly organized Tokyo Symphony Orchestra until the Great Kantō earthquake of 1923 "disorganized all the business and musical interests of the city". The couple fled Japan and arrived in San Francisco in November 1923. They eventually made their way to Portland in 1924; it was here that Gershkovitch was approached by Dodge to lead the Portland Junior Symphony. Gershkovitch taught flute and conducted the Ellison-White Conservatory's student orchestra, at the time directed by Jacob Avshalomov, until his new PJS duties required his full attention.