The search for “smart” or Information and Communication Technology (ICT) based mobility solutions goes back to at least the 1960s. The Provo anarchist Luud Schimmelpennink is well-known for designing mobility solutions and for being the driving force behind the 1965 “white-bike” experience. Less known is his 1968 project for shared electric cars (“Witkar”), which laid the foundations for the ICT-based bicycle sharing systems as we know today. By combining his talent for innovation with activism, he created a socially embedded design that could be part of the public transit system. Based on primary sources, we argue that these sociotechnical experiences paved the way for today’s mainstream bicycle sharing projects worldwide. We then show how since the 1990s, the Dutch railroad’s public transit bicycle (OV-fiets) has transformed Schimmelpennink’s original anarchist idea of bike sharing into a sustainable public transit system – a feat that has eluded other programmes worldwide: the integration of the bicycle’s share in a door-to-door experience.