Established firms face the challenge of managing entrepreneurial strategies in order to respond effectively to major environmental changes. This paper uses a simulation methodology to explore the effectiveness of several entrepreneurial strategies in established organizations when they are faced with a fundamental restructuring of their environment. The simulated organizations are characterized by high and low levels of entrepreneurial activity and three types of entrepreneurial strategies: fixed, imitative, and adaptive. The behavior of these organizations is guided by the assumptions of an organizational learning model. The results of the simulation indicate that, given the assumptions of a learning model, there are several lessons that established organizations should consider in managing entrepreneurial strategy. First, there are important organizational implications under different levels of ambiguity. Second, lessons learned from past experience can often result in learning traps when the environment changes. Finally, conceptualizing organizations as characterized by different entrepreneurial strategies and different levels of entrepreneurship provides a theoretically useful description of differential outcomes in terms of performance, growth, and the probability of failure. [ABSTRACT FROM AUTHOR]