Returning to Massachusetts four years later, he worked for several years in his father’s shop as a printer’s apprentice. He had read about Benjamin Franklin’s success and decided to model his own career. He opened his own needle and thread shop in Boston in 1844, but it soon became bankrupt. Macy was described as a stocky guy, and was frugal and hot tempered (Macy).
Unfortunately, Macy’s business did not work out as well as it did for Ben Franklin, so with the backing of one of his brothers, he opened his first dry goods store in 1843 but this store also failed (Profiles in Greatness: Rowland H. Macy). He briefly worked in his brothers law shop in Boston, but then fled to California in 1849 for the gold rush. He came back home with about $4,000 and a wealth of new life experiences, and then he went back to Massachusetts and opened the first Macy’s store in 1851, in partnership with his brother. This store was a great success but it ultimately failed and the 36 year old had no intention of giving up. Macy had learned from his mistakes.
He moved to New York City in 1858, and started R. H. Macy Dry Goods on the corner of Sixth Avenue and 14th Street. Macy found major success in New York. The store had only about 11 feet of frontage,