Ives worked as a bank clerk for Guaranty Trust Company in New York City from 1920 to 1923, earning $25 per week. In 1920, he married Elizabeth Minette Skinner, to whom he remained married until her death in 1947; the couple had one son, George. Joining Manufacturers Trust Company in 1923, he was placed in charge of the bank's business activity in Upstate New York and subsequently moved to Norwich. He remained with Manufacturers Trust until 1930, when he entered the general insurance business in Norwich.