Olenicoff was born in Moscow in 1942. After the war, his family being tsarists, fled the Soviet Union for Iran where he was educated by missionaries. In 1957, his family emigrated to the United States. In the U.S., his Father Michael, an Engineer, worked as a janitor, and his mother, Zina, worked as a housekeeper. He graduated from the University of Southern California with an undergraduate degree in corporate Finance and mathematics as well as an M.B.A.