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Abstract All over the world there are millions of social entrepreneurs that come up with potential social innovations. Some never get implemented in practice. Others are implemented, but then the passion fades or the solution does not reveal itself as promising for creating social impact. In some cases, the lack of sustainability or management capacity prevents a successful scaling up process. Despite all these potential obstacles, there are social innovations that go from promising ideas to becoming mainstream solutions, leading to new markets, industries, or social movements, such as Microfinance or Wikipedia. An in-depth look at main obstacles facing social innovators and the leadership skills required to overcome them is a meaningful contribution to the field of social innovation. The goal of this chapter is to propose such a contribution through an in-depth exploration of the life cycle of social innovation. The term “life cycle” implies a sequence of stages in the evolution of new ventures (Parker 2007).