Given the desperate plight of urban schooling and the disheartening track record of conventional reform, dynamic new ventures like the KIPP Academies, Edison, or Green Dot Public Schools are increasingly being asked to stand in for failing district schools. While promising, these ventures have thus far typically been characterized by "one-off" examples of success that are extraordinarily reliant on talent and passion, philanthropic funding and exhausting work schedules. A less popular but more promising course, and the one explored in this monograph, is to help successful new ventures grow in a more sure-footed manner by considering how factors that fed early success may need to be revisited. While there are lessons for traditional K-12 districts, the challenges associated with changing established districts are substantially different from those faced by charter networks and charter management organizations (CMOs). The focus here is on how nontraditional educational entrepreneurs can help themselves "grow smart." (Contains 1 table and 15 notes.)