This conceptual study describes an approach to corporate entrepreneurship using an outsider perspective–learning to think like an outsider. Three propositions using this perspective are examined in the context of offensive and defensive corporate entrepreneurship. The impact of market conditions on entrepreneurship are used as a basis for developing these propositions. Finally, we investigate the factors that have a significant impact on the success of entrepreneurial efforts by the firm. These variables include: processes, values, resources, organizational structure, corporate culture, and leadership. We use examples of how mature corporations have responded, with particular attention to the changes confronted by Research In Motion (RIM).