He immigrated with his family to the United States in 1986 during the apartheid era because his father Nissen started an electronic-engineering business in Philadelphia.[6][7] In Philadelphia, he began touring with a band at the age of 16.[3] Isakov later moved to Colorado to study horticulture at Naropa University.[8] Isakov had played instruments his whole life, but began a life as a professional musician playing occasional gigs while also working as a gardener.[7] His musical career became more serious when he began touring with Kelly Joe Phelps.[8]