Social entrepreneurship—a new business model that combines a social goal with a business mentality—is in a transitional phase, from a rough cowboy market to a more established market niche. This process results in two interconnected dilemmas for the social entrepreneur. First, how it can capture market share despite its role as an antagonist to current market values. Second, how it can prevent the loss of its own core values in the course of greater interaction with the incumbent regimes. Using a tool known from innovation sciences to analyse radical innovations, namely strategic niche management, and both survey data and interviews from actors in the Netherlands, this article shows that social entrepreneurs have an attitude that is still more in line with the cowboy market than with the new diplomatic role they are expected to take on. Subsequently, it provides recommendations on how to achieve this new attitude.