We present a case study of Santiago a Mil, founded in 1994 and now one of South America’s most successful theater festivals. We look at the evolution of the business model of this festival, a private initiative in Santiago, Chile, launched by two cultural entrepreneurs with strong social values. We identify four periods of business model evolution related to the context of this festival. We address how the festival has recently adapted to a difficult local context, strengthening its connection with audiences and the public, both live and through social media. We underline some factors in the external context and in the entrepreneurial profile of the two founders that may have influenced how the festival’s business model evolved over time. We discuss the role of festivals and cultural entrepreneurs as social actors that impact today’s world, when protests are increasingly orchestrated on social media.