This thesis explores the challenges and opportunities of cultural entrepreneurship, exploring current conceptualisations of cultural entrepreneurs and to find new perspectives and recommendations for cultural entrepreneurs of the future. Cultural entrepreneurship is a contested, yet essential aspect of the growth of artists and arts organisations globally. Though there are similarities, this research demonstrates that cultural entrepreneurs from different backgrounds, industries and of varied sizes need different things and have different barriers so cannot be understood in the same way. Digital technologies and local networks do offer new possibilities for innovation however these are limited in scope and require further investigation and investment. Despite psychological, political and financial barriers to entrepreneurship in the creative industries, finding a balance between artistic, social, economic and institutional innovation for the various actors throughout the arts offers key insights to how artists and arts organisations can be more entrepreneurial.