The historiography of the American bicycle industry is overwhelmingly a story of men’s successes and failures in major corporations. The few historians who have incorporated women into bicycling research have only considered women as consumers and there is no scholarship which recognizes women as innovators and producers in the bicycle industry. This gap in women’s history and the history in sport is due in part to the assumption that women were unable to carve out a space in this male-dominated industry due to the widespread barriers limiting nineteenth-century women from business and innovation. This paper complicates this assumption by exploring women’s multifaceted involvement in the turn-of-the-century bicycle industry as inventors, saleswomen, mechanics, and builders. Women’s work often took place outside of the borders of nationally known bicycle corporations and on the local level. In these periphery spaces of industry, women could tinker, develop new products, and build businesses. Wheelwomen used their daily experiences as cyclists as the inspiration and authority to actively shape the bicycle industry to meet their needs, achieving successes understood on their own terms. These successes ultimately challenge historians to rethink how historical actors experiencing rampant inequalities can still ‘win’ in business.