This chapter sets out to explore the field of leadership development and its emerging contribution to sustainable entrepreneurship; why there is a need to develop research and effective practices in this area, and how this might be achieved. It studies the questions of how organisations can generate entrepreneurial leadership for their longer-term sustainability; how they can develop a sustained culture of entrepreneurship; and how they can facilitate people into leadership roles, which enable continuing innovation, development and growth. The research is based on four case studies developed from research with entrepreneurial leaders in selected organisations. The leaders had founded or led their organisations for significant periods, and built them up to achieve a level of success, scale and structure. Their organisations include private, ‘for-profit’, community, and social enterprise organisations, but all have a strong sense of ‘community’ identity and sustainability. The interpretation of the cases revealed the importance of the leaders’ principles and ethical values in articulating a vision for what the organisation could achieve. They practised deep community involvement to build trust, by connecting with individuals, families and groups. There is continual scanning for needs and possibilities for social innovation to address problems and create multiple forms of value, connecting latent resources to enact opportunities. Their approach to leadership is distinctive, rather than imitative of other organisations, whilst finding and growing human talent and social capital to develop the organisation is seen as essential for the future.