The characteristics of digital entrepreneurship and digital transformation and how they are related, is complex and important to understand in this digital age. Such an understanding of digital entrepreneurship is perceived as a key pillar for economic growth, job creation and innovation. However, a number of issues regarding digital entrepreneurship and digital transformation are prevalent, inhibiting digital entrepreneurs to optimise the advantages that digital entrepreneurship contributes towards business value. Therefore, the aim of this research paper is to investigate digital entrepreneurship and digital transformation, their characteristics and inter-relationships. Data extracted and analysed through a structured analysis process, recognises and discusses the characteristics of digital entrepreneurship and digital transformation. The characteristics are reported by employing the Dynamic Capabilities Theory as the structure. By understanding the characteristics of digital entrepreneurship and digital transformation, individuals and organisations may either create new business ventures or transform existing businesses through the development of novel digital technologies or the innovative application of such technologies.