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Entrepreneurship is an important competence to effectively deal with the challenges of today’s working world. In this chapter we will present theoretical models and empirical research on the development of entrepreneurial interests, attitudes and behaviour. Following David McClelland’s model (1966) on the development of entrepreneurial activities, we demonstrate that an entrepreneurial personality profile identified as early as in adolescence, as well as a stimulating environment (e.g., in the family of origin), relate to entrepreneurial activities later in life through the development of entrepreneurial competencies and interests. Our expectations are supported by data on adolescents, students, business-founders and the famous Terman Life Cycle study. Moreover, ways to foster early entrepreneurial motivation and skills through intervention programs are discussed.