This study examines the progression of e-business in eight small and medium enterprises (SMEs) using a stage model as a framework to explain the evolution of their e-business initiatives. In particular, the paper reports on the issues, barriers, and challenges that influence the progress of an e-business initiative. Most prominent are the issues of the perceived value of e-business, stewardship of e-business, and management commitment. We found that in order to gain a satisfactory pace of e-business progress, companies need to resolve these issues satisfactorily. Finally, using pragmatism as a theoretical lens through which to interpret the comments of the participants, it can be established that the stage model used in this study is an important guide to assist the management of SMEs to progress through with their e-business initiatives.