History encompasses some singular sequences of events and conditions that create entrepreneurial opportunities. This paper looks at the historical settings of the second and third waves of industrialization to consider the emergence and evolution of the express industry, whose origins date from mid-nineteenth century America. By using sequential historical rea-soning, this work determines how these different settings created entrepreneurial opportunities and how entrepreneurs in the express industry exploited them through innovative responses that went on transforming the nature of the industry through time.