This article uses the records of the National Negro Business League (NNBL) to examine the economic life and experiences of African American entrepreneurs between 1900 and 1920. Often referred to as the ‘golden age’ of Black business, this era saw the proliferation of African American owned businesses, despite the increase in discrimination and racial persecution that had characterized the United States since the turn of the century. Far from merely a platform to reaffirm the ideology of its founder Booker T. Washington, the League enabled a diverse group of business owners, entrepreneurs and professional men and women to exchange ideas and help one another navigate the segregated and uneven infrastructures of American capitalism. The protocols of the League’s annual conventions offer a window into the world of Black proprietors and shopkeepers. Specifically, the personal accounts delivered at these events reveal the experimental commercial sphere that existed next to the well-established trade and business institutions of corporate capitalism. They also demonstrate that the members of the NNBL were a progressive force: they confounded gender norms by carving a place for women within the formal Black business establishment and they diversified the economic playing field by charting alternative narratives of business success.