[1] He went to sea at the age of 13 and traded between Sydney in Australia, the Pacific Ocean, China, and Auckland in New Zealand.
[1][2] In the following year, he traded with his 150-ton schooner Pauline in New Zealand, and his first consignment was kauri pine that he sold to Henry Le Cren of Lyttelton.
[2] The Pauline was lost during a June 1851 storm in Lyttelton Harbour that claimed a total of five vessels,[3] and he bought the vessel Kaka to transport goods between Lyttelton and the Ferrymead wharf on the Ōpāwaho / Heathcote River for Christchurch under contract for Le Cren and his business partner, Joseph Longden.
[2] In 1857, he was asked by Le Cren to set up a trading post in Timaru,[5] then merely a sheep station owned by George Rhodes.
[11] The Timaru Herald reported on Cain from "their archives" as part of the 150th anniversary of their first publication in 1864.