This chapter examines the factors that promote entrepreneurial projects in established companies. A set of forty triggers is proposed and ways in which triggers can be classified are suggested. A conceptual model links types of triggers to specific types of entrepreneurial projects and to outcomes. To test the model, surveys were conducted with companies in South Africa and the United States. The results for the two samples are similar, and indicate that triggers tend to be more internal and planned, that the type of trigger is related to how innovative the projects tend to be, and that planned entrepreneurship is associated with greater success.