The term ‘digital’ concerns not only technology but also people. This chapter emphasises the necessity of adopting a digital entrepreneurial mindset when operating in a digitised world. The chapter proposes a definition of a digital entrepreneurial mindset that is rooted in cognitive psychology, organisation theory and entrepreneurship literature. We also focus on the five trends that are shaping the digital future: mobile computing, cloud computing, social media, the Internet of Things and Big Data. The chapter discusses the challenges and opportunities that pervasive digitalisation offers for designing new digital business models and changing interactions with customers. Discussing the success stories of Domino’s Tesco and Tate Art Galleries helps to examine data-driven, cloud-enabled, platform-centric business activities, for which developing a digital entrepreneurial mindset is the first step towards success in the digital age. Collectively, the aforementioned cases suggest that businesses that rely on a digital entrepreneurial mindset enjoy better financial performance. Both managers and employees in these companies have shown the inclination and ability to discover, evaluate and exploit opportunities emerging from digital technologies. This chapter also provides a practical guide for entrepreneurs on the steps they can take to encourage a digital entrepreneurial mindset throughout their entire organisations. Finally, we elaborate on the practical implications of adopting a digital entrepreneurial mindset and its impact on society.