Roland Hussey Macy, the founder of the U.S. chain of mid-range department store is yet another famous entrepreneur who had to face bankruptcy in his early days. Macy filed bankruptcy in 1855 after failed business.

Macy left home at the young age of 15 to sail the Atlantic with whale hunters. Four years later he returned to Massachusetts and started working in his father’s shop.  After that he started his own needle-and-thread store in Boston in 1844, but it was soon bankrupt. Macy began selling dry goods in 1846, but this store also failed. He briefly worked in his brother-in-law’s Boston shop, and then fled to California in the 1849 gold rush. Finding no wealth out west, he returned to Massachusetts and opened a dry goods store in Haverhill. In 1858, Macy left Haverhill even though the store was a modest success, and opened a small store of his own R.H. Macy & Co. in New York City.

In New York, Macy found major success. His store became known for revolutionary ideas such as fixed prices where items were sold at the same price to every customer rather than be bargained for and advertisements in newspapers. Now, the flagship Macy’s store in Herald Square is the single largest department store in the world!