The aim of this research is to explore those competencies within the entrepreneurial small firm, (ESF), which will determine if it is to adopt and fully exploit the potential of the Internet in developing and maintaining relationships with its customers. A key relationship, and one that is a major focus of much of the relationship marketing literature, is that between the supplier, in this case the ESF, and the customer or buyer. In this research, using a qualitative methodology, the authors examine the nature and character of the challenges faced by 30 entrepreneurial individuals in their relationship-oriented utilisation of the Internet. As a first stage of a larger research programme it explores the competencies likely to determine the extent of Internet adoption. The paper offers insights to a more complete competency spectrum for Internet marketing in the ESF.