Richard Warren Sears was 16 in 1879 when his father lost the family fortune on a speculative stock deal and died soon after. Working as a railroad station agent in North Redwood, Minnesota, he watched a local jeweler refuse a shipment of pocket watches, bought them himself, and sold them to other agents up and down the line. Using the telegraph wire, he turned station agents who knew everyone in town into a sales force that undercut the local jeweler. By 1886 he had a mail order watch business in Minneapolis, and by 1887 he and watch repairman Alvah Curtis Roebuck were publishing a catalog from Chicago.

This episode traces the restless career that followed: selling the business for $100,000 at 26 to become a rural banker in Iowa, returning in 1892, and growing the catalog past 300 pages. When the Panic of 1893 froze the company’s cash and Roebuck wanted out, Sears pitched his own creditor, Julius Rosenwald, on buying in. The dreamer and the operator together built a retail giant, and the pace of it broke Sears’s health.

• In August 1895 Julius Rosenwald and his brother-in-law Aaron Nusbaum bought Roebuck’s half of the company for $75,000.
• Sears often advertised goods he did not yet have in stock, while Rosenwald built a time stamped system of chutes and conveyor belts so every item in an order reached the packing room in the same minute.
• The 1906 stock placement raised $40 million and funded a 40 acre complex on Chicago’s west side, and by 1908 failing health forced Sears to resign the presidency.
• During the agricultural depression of 1919 to 1921, Rosenwald pledged $21 million of his own wealth to keep the company alive.
• With cash on delivery and rural free delivery, the catalog let Black customers in the Jim Crow South bypass white-owned general stores and pay the same price as anyone else.