The Strugglers story began in 1967 with the arrival in Wellington of Bill Lake to study philosophy at Victoria University. Previously a member of Canberra jug band the Garden City Strugglers, Bill had left Australia to avoid conscription (the Vietnam war was escalating), bringing with him an extensive collection of blues and jug band records. He was soon recruited to play harmonica and mandolin in a campus-based group The Kelburn International Airport Ceremonial Guard Band, who followed the popular Jim Kweskin adaptation of traditional jug band music. Formed specifically for a University Arts Festival, the life of the KIACGB was short but most members went on to greater successes in other musical contexts.

In spite of his quiet demeanour, Bill's reputation as a peerless interpreter of arcane rural blues quickly spread. In the liner notes to In the Blue Vein, a late-60s compendium of capital city blues, Midge Marsden referred to "Honest Bill Lake" as "the best damn blues player in the country".

In 1968 Bill was approached to sing in the blues concert at New Zealand's National Folk Festival. He recruited the Rashbrooke brothers, Geoff (piano) and Mike (jug) from the Kelburn International Airport group to accompany him, and the Windy City Strugglers were born.  The performance, which featured Bill on mandolin and vocals, included Sleepy John Estes numbers and impressed local critics: "It has that authentic shaky sound you hear on the old records", said one.