Wikilearning is self-organized and self-determined by nature, and has a simple common goal – editing a wiki page. It enables and leans on voluntary participation, altruistic sharing of ideas and resources, and anonymous collectivism. At best it exceeds the orthodox boundaries of formal schooling and other exclusive practices of education, and contains an ideological and political message. It highlights people’s knowledge, and aims to promote a world in which knowledge production is democratic and equal among all peoples. In this chapter we analyze our experiments with wikilearning both in Finnish upper comprehensive school and at the university. We conclude that wikilearning is among the components of any reinterpretation of what it means to educate new generations into Democracy 2.0. Because of its collaborative style of knowing, wikilearning belongs to the toolbox of teaching and learning in developing and nurturing democratic minds and democratic collectives both inside and outside the classroom.