As part of the general curricular ambitions of contributing to the development of a democratic society, Swedish schools are mandated to actively combat racism and extremism. This causes particular challenges when teachers encounter students who have been brought up in environments where racist and extremist worldviews dominate. This study analyses four Swedish neo-Nazi leaders' experiences of schooling and how they have utilised these experiences when establishing an approach for their children's schooling. The focal point of the analysis is the ideological dilemmas that arise from clashes of conviction among neo-Nazi leaders, their children and the teachers. The results show how neo-Nazi leaders use their own negative experiences of schooling to prepare their children on how to escape both democratic education and prevent social stigmatisation.