We propose that competitive success and failure evolve through an ecology of organizational learning. An organization facing competition is likely to engage in a search for ways to improve performance. When successful, this search results in learning that is likely to increase the organization’s competitive strength, which in turn triggers learning in its rivals—consequently making them stronger competitors and so again triggering learning in the first organization. We elaborate the conditions under which this self-reinforcing process, known in evolutionary theory as the ‘Red Queen,’ is likely to be adaptive or maladaptive. Adaptive consequences are predicted only for recently experienced learning. Experience in the more distant past of an organization’s life, by contrast, is predicted to backfire into a ‘competency trap.’ We predict maladaptive consequences when organizations face many, varied cohorts of rivals. We empirically distinguish these effects using ecological models of competition. Estimates of organizational failure rales reveal a Red Queen among Illinois banks, and support our predictions.