In his business career, Keane asserted that he was “self-made,” with no inheritance from his father. After apprenticeship in the Merchant Taylors’ Company, he took a shop in Birchin Lane, a street where the sellers of clothing displayed their wares. Either because of his fortunate marriage to the daughter of a gentleman or, more likely, because of success in business which enabled him to accumulate an estate of some £2000 or £3000, he enjoyed the modest rewards of a prosperous citizen, such as membership in the Honourable Artillery Company of London. His routine business included supplying liveries for the pages and footmen of the Lord Chamberlain. Keane was associated with James Sherley and the other merchants who furnished Plymouth with capital and direction. With Sherley he signed a letter to the colonists in 1624, and Peirce mentions him as an “assistant.” In the list of 1626, Keane was among the five designated to receive the £1800 to be paid by the Colony. In the Massachusetts Bay Company he was one of the inner ring of “Undertakers.” Keane was also the leading spirit in the organization of the Ancient and Honorable Artillery Company of Massachusetts. He served as the first captain of this military company, the earliest to be chartered in America. The religious pressures upon a conscience like Keane’s are unmistakable, for amidst all the troubles he suffered in Massachusetts he described the new commonwealth, in its closeness to the Gospel, as little different from that which had summoned him to leave England in 1635. Of those who came to Boston, he was remarkable for his wealth and his successful application of it to new kinds of profitable transactions, such as investment in land and trade to Bermuda or the West Indies. In time, he installed his son, Benjamin, in Birchin Lane in London to act as his agent and to sell cloaks. Keane’s career is a model of the intertwining of “merchandise, reading and writing,” all matters of importance to Puritans anxious to redeem their time on earth.[30]