Joseph Spiegel worked as an apprentice in several retail stores in New York until 1862, and in 1863 he enlisted in the 120th Ohio Volunteers. He served in General Ulysses S. Grant’s army in Louisiana where he acted as sutler to his brother's regiment, witnessed his brother’s death in battle, and was later captured and sent to the prisoner of war camp at Fort Camp, Texas, where he remained until May 1865. He returned to Chicago where he entered the furniture business with his brother-in-law, opening a small furniture shop on Wabash Avenue named "J. Spiegel and Company" which sold Liebenstein furniture. In 1870, he assumed control of the Liebenstein business after marrying Liebenstein's niece, Mathilde Liebenstein. The Chicago Fire of 1871 destroyed his business, although he was able to quickly restart since most of his inventory had been stored at his undamaged house, which led to a boom as fire victims needed to repurchase furniture. In 1886, his sons, Modie and Sidney, joined the business. In the 1890s, as wealthy clientele moved to the suburbs and were replaced by immigrants, Spiegel shifted the company's strategy from selling high-quality furniture on a cash-only basis to cheaper furniture on credit. In 1903, his son Arthur joined the business and Spiegel started their mail order catalog business, becoming the first company to sell furniture by mail. By 1925, the fashion and furniture retailer had 10 million customers.