This essay analyzes the changing configuration of black-owned businesses in the South over nearly a century. It divides the region into two sections—the Lower South and the Upper South—and examines changes that occurred prior to 1840, during the late antebellum era, and as a result of the Civil War. It uses a “wealth model” to define various business groups, and then creates business occupational categories based on the listings in various sources, including the U.S. censuses for 1850, 1860, and 1870. The article compares and contrasts the wealth holdings among various groups of blacks in business, and it analyzes, within a comparative framework, slave entrepreneurship, rural vs. urban business activity, color—black or mulatto—as a variable in business ownership, and slave ownership among blacks engaged in business.