Intended for educators who work with or plan to establish a school-based enterprise (SBE) in their school, this guide provides tools and strategies to establish and operate an SBE that provides a context for students to learn a range of academic and career-oriented skills. Section 1 suggests steps educators can take to help their enterprise--an SBE integrated with the school's curriculum--succeed within the school setting. Section 2 describes ways to incorporate planning into setting up an SBE. This business planning process guides students and teachers through the research and investigation needed to create a viable business that meets a need in the school or surrounding community. At the end of the section are nine "tools," activities and forms teachers may wish to use to accomplish the steps to help them get the SBE off to a good start. Each tool consists of some or all of these components: purpose, materials, time required, procedure, reflection, bridges, teacher forms/materials, and handouts. Section 3 provides strategies teachers and administrators can use to augment the learning students derive from an SBE once it is up and running. These strategies are also designed to have a positive effect on the enterprise's profitability, which in turn determines the SBE's ability to generate revenue for social benefits. At the end of the section are tools useful in accomplishing the five strategies. Contains 12 references and an appendix on business and management competencies (student records). (YLB)