Lifestyle non-economic motives have been recognised as a significant motivational factor for tourism and hospitality entrepreneurs. However, knowledge on the subject is mainly drawn from the perspective of western developed economies, with a paucity of studies focusing on transition and developing countries. The purpose of this paper is to investigate tourism entrepreneurship within the former socialist countries, particularly focusing on Croatia. The study is based on in-depth interviews with tourism entrepreneurs in the Splitsko-dalmatinska county (Split-Dalmatia). The paper argues that understanding of entrepreneurship can be enhanced if theories are contextualised within a specific setting and industry sector, and thus applies the “drilling down” model in investigating tourism entrepreneurship. The results reveal a non-existence of lifestyle entrepreneurs and a conceptual model is developed to encapsulate the complex range of factors which underpin the different behaviour of the analysed entrepreneurs. Implications for entrepreneurship theory and further research are discussed.