If our contemporary society needs innovative solutions we argue that we need to learn from our youth. This paper presents the most prevailing issues that arose during the collaborative digital art project designed to connect our youth with big, mainstream cultural institution, and to augment the outreach of the project. By using the research through design approach and surveys with participants, we analyse the implications introduced by inter-institutional and interdisciplinary collaboration. We claim that such collaborations are rich, but expensive and risky. Still, they are powerful mechanisms for learning new concepts, developing creative and critical thinking, and above all social capital acquisition.