The portfolio management models (PMM) has emerged as an important idea in educational governance over the last decade. In PMM systems, a district or other form of authorizer oversees a collection of independent organizations that operate schools according to their particular philosophy and strategic orientation. Yet underlying the design of PMMs is the assumption that the individual operators have the capacity and wherewithal to make strategic adaptations to their strategies based on results and other types of feedback. However, environments that present formidable challenges to school operators may place demands on operators that surpass their capacity to adapt on their own. In such cases, providers can collaborate to learn from one another, or the authorizer can provide effective albeit centralized learning opportunities. A three-year study of the Tennessee Achievement School District (ASD) found that the design of PMMs can greatly complicate the possibilities for collaborative or centralized learning. One reason for this is normative in that a competitive environment does not foster an ethos of collegiality. A second reason is that the extreme variation in curriculum, instructional philosophy, and other educational tools and processes creates a thin basis for collaborative exchange. The article concludes that systems designed to promote collaborative learning may be better aligned with demanding environments than PMM or other market-based systems.