He was a merchant with an eye for a good thing who gradually became involved with banking and insurance and founded Bermuda's oldest bank (N.T. Butterfield & Son, Ltd.) and Bermuda's oldest insurance agency (C.N.A. Butterfield & Son, Ltd.). The two split apart in the early part of the twentieth century with the bank becoming a public company while the insurance agency remained a family business. There is still a client who according to family members (records are hard to come by before the twentieth century) has been covered continuously since 1815.