Venture failure has been studied from the entrepreneur’s perspective through previous qualitative research. However, very few studies have considered the specific business environment in which entrepreneurs operate. This thesis addresses entrepreneurial failure and focuses on the EU healthcare sector. The paucity of academic research combining the lived experience of venture failure and the healthcare industry context, highlights the importance of this study. An interpretative phenomenological approach is used to provide situated insights, rich details and thick descriptions of participants’ experiences whilst allowing appreciation of the business context and development of common themes. Through in-depth interviews with seven entrepreneurs, this study develops a deeper understanding of what it is like to experience venture failure in the healthcare industry. Findings show that entrepreneurs were not only deeply affected by emotional hardship, but also suffered from detrimental social consequences as a result of stigmatisation and no longer being part of the healthcare industry. Findings suggest there is a relationship between entrepreneurial optimism, post-failure effects and longer-term outcomes, with a central role for healthcare entrepreneurs’ intrinsic motivation. This work adds empirical weight to the existing body of entrepreneurial failure theory. The exclusive focus on the healthcare industry adds a new perspective to academic theory and is also of value to entrepreneurship practice. Entrepreneurs’ genuine desire to make a difference in healthcare, despite the industry’s complexity and the challenges it entails, deserves more attention from policy makers, investors and other stakeholders in the healthcare ecosystem. Finally, the insights derived from the narratives of entrepreneurs who experienced failure, might help other entrepreneurs in their endeavours.