The family was living in Spring Valley, Minnesota, by June 1870, where his father served as a city councilman and eventually sold his wagon shop in 1875.

A common scam existing at the time involved wholesalers who would ship their products to retailers who had not ordered them.

Young Sears jumped at the opportunity, and made an agreement with the wholesaler to keep any profit he reaped above $12, and then he set about offering his wares to other station agents along the railroad line for $14.

He took the personal approach in his ads, speaking directly to rural and small-town communities, persuading them to purchase by mail-order.

By 1897, items such as men's and ladies clothing, plows, silverware, bicycles and athletic equipment had been added to the offering.

In 1908 Sears made another move forward and began to sell mail order homes through the catalogs.

In 1908 Sears retired and moved from Oak Park to Lake Bluff, Illinois, suffering from failing health due to alcoholism.