This chapter describes the emergence of an entrepreneurial approach to cultural management in the late 1990s. Behind this transition to ‘Cultural Management 2.0’ lay a number of political, technological and cultural changes. In cultural policy, an investment of belief and resources in the creative industries, typified by the UK creative industries policies from 1997 under New Labour, highlighted the commercial and creative potential of small independent commercial creative enterprises. Digital technology opened the way for a new generation of digital intermediaries but also created opportunities for creative and media enterprises able to adapt to rapid technological change. And the use of ‘creativity’ as a companion to management rather than an antonym signalled a shift in the way businesses thought about creativity, and artists thought about management. The chapter argues that Cultural Management 2.0 bridged the opposition between creativity and management under Cultural Management 1.0 by idealising the multitasking, adaptable cultural entrepreneur. Yet whilst resolving some dilemmas of Cultural Management 1.0, Cultural Management 2.0 exposes other problems – in particular, the strategic challenges of managing sustainability, growth and organisational change. The chapter concludes by weighing up both the flaws and successes of Cultural Management 2.0 as the dominant paradigm of cultural management.