This paper investigates the ways in which entrepreneurs use communities of practice (CoPs) to express themselves, using narrative theory and rhetorical analysis, to gain insight into an electronic social network medium, namely, YoungEntrepreneur.com. In particular, the study focuses on CoPs themes, including why entrepreneurs engage in CoPs, what role the moderators and resident entrepreneurs can play in managing online CoPs, on communication rituals of the knowledge sharing through interactivity, and on ‘how to develop an intervention’ to maintain and stimulate entrepreneurs for engaging in an online community. Findings reveal that the topic title plays a major role in attracting people. Successful topics with successful conclusions (in terms of the original query that was answered) will not necessarily get high responses and vice versa. It is observed that the domain expert does not play a big role in keeping the discussion going. Finally, the study also discovered that entrepreneurs like to communicate in a story telling genre. A comprehensive set of engagement measurement tools are introduced to effectively measure the engagement in a virtual CoP, along with a classification to define and categorise discourse of messages in terms of content and context, which allow practitioners to understand the effectiveness of a social networking site.