Founded by Booker T. Washington in 1900, the National Negro Business League (NNBL) sought to unite Black business owners, promote entrepreneurship, and develop economic power. Despite its prominence in the early twentieth century, the group declined after Washington’s death in 1915. As a result, little is known about its organizational development. This study uses data on state and local Negro Business Leagues (NBLs), along with active and life members of the NNBL, to better understand the group’s first fifteen years. Analyses reveal that the NNBL’s development reflected closely the social and economic context of early twentieth century Black America. Generally speaking, the NNBL was stronger in states with larger urban Black populations and where the value of Black-owned farms was higher, consistent with the importance of agriculture to Black business during this era. These results both shed light on the NNBL’s early success and suggest avenues for future research on its decline.