 Beginning in January 1855 he served as a cashier's clerk in the Bank of Commerce in New York City, under his uncle, John Austin Stevens, the president of the Bank.After two months of travelling in Cuba, he became a clerk in his brother's store in New York City in May 1856.In early 1857, his elder brother Albert took him into partnership under Stevens, Angelo & Company, and they ran a sugar commission business with Cuba until 1868.