This dissertation explores competitive market dynamics and firm configurations of resources and capabilities as a complex adaptive system using a computer simulation. The work is an extension of the broad literature on strategy-environment alignment, integrating concepts from the organizational literature about strategic types, organizational evolutionary dynamics, the resource-based theory of the firm, microeconomics, and artificial intelligence to create a simulation system that makes the process of market evolution with heterogeneous agents available for experimentation. The work provides a means to model and study complex dynamic systems, such as evolving agents and markets, and reveals how such chaotic systems can support and undermine strategic actions initiated by agents. Results both corroborate and diverge from received theory concerning competitive advantage and luck.