He was born in London the son of a violinist who died in the 1st World War. Ken, as he was known to his friends was brought up in poor circumstances but vowed to make a finacial success of his life. He did not attend university but he was blessed with a talent for business. He came to the attention of Vernon Sangster who had inherited Edmonds, a Manchester store which had a small side business of collecting bets on football results from punter in pubs. Kennerley formed this into Vernons Pools and became its MD. Later he ran the New York State Lottery and also became the chairman of the Football Pools Association.
Apart from business his other great love was post-impressionist painting. He decided to learn to paint with his good friend John Moores, the millionaire owner of Littlewoods Pools. Moore soon dropped the idea but Kennerley persisted and became an inventive draughtman and colourist. He regulary sold work at The Royal Academy's annual shows and Liverpool's Walker Art Gallery hold examples of his work.