Entrepreneurs are talked of as “the heroes of our times” and more heroic than all others are the entrepreneurs who engage in more than one venture. This paper aims to advance entrepreneurship theory through showing empirically that serial entrepreneurship, or rather serial-startups, isn’t necessarily a deliberate choice. This is illustrated by three selected cases, which we have followed through longitudinal qualitative studies. Theoretically, our analysis has profound implications, since it questions the notion of start-ups as a measure of economic success of individuals, regions or nations. The paper also explores the previously understudied exit-part of the entrepreneurial process.