This paper seeks to help social sector leaders understand the factors that they should consider when launching revenue-generating business ventures. Given that much of the research on social sector business ventures is based on the personal experiences of individual practitioners, there is a wide array of advice for organizational leaders who are thinking about launching business ventures. Consequently, we approach the subject of social sector business ventures in a systematic and analytic way in order to determine what organizational leaders really need to know about launching successful ventures. We introduce a framework called “business in a box” that separates the process of thinking about launching business ventures from the organizational characteristics and dynamics that influence these ventures. We assert that organizational leaders who wish to maximize the success of their business ventures must explore (1) what is “inside” the box (The Business and its Context) to understand the business fundamentals of launching a venture and (2) what is “outside” the box (Assets and Internal Destructive Forces) to understand the forces and dynamics within the organizational context that impact these ventures.