He was clearly a loser as an entrepreneur. At 36, he had already failed at four different retail businesses on both coasts. "I have worked two years for Nothing," he wrote in his ledger at one point. "Damn. Damn. Damn. Damn."

But he decided to try a fifth time. In New York City in 1858, he secured credit from some wholesalers and opened a modest dry-goods store far from the main retail district. The new store recorded first-day sales of a paltry $11.06. But his low prices and his strict policy of cash-only sales, which was unusual at the time, brought quick success this time around for Rowland H. Macy.