This study explores how educational champions--teachers who initiate unsolicited innovation--construct their entrepreneurial endeavors while interacting with principals' management styles and how that interaction influences the sustainability of teachers' initiatives. Through semistructured interviews (N = 71) and analysis anchored in grounded theory, champions revealed three entrepreneurship strategies: semiautonomous entrepreneurship while interacting with a facilitative managerial style, loosely coupled entrepreneurship with directive management, and sponsored entrepreneurship with consolidative management. Analyses of these entrepreneurial endeavors illuminate teachers' strategies for negotiating the ongoing tension between autonomy and control in schools and their influence on the sustainability of champions' innovations. (Contains 2 tables and 5 notes.)