In this paper we employ theories of experiential learning to examine why some entrepreneurs have developed a more positive attitude towards failures compared to others. The empirical findings support our guiding proposition that more favourable attitudes towards failing can be learned through entrepreneurs' life and work. Our results suggest that previous start up experience is strongly associated with a more positive attitude towards failure. Moreover, we also find that experience from closing down a business is associated with a more positive attitude towards failure. In sum, our findings add to our knowledge of why some entrepreneurs have a more positive attitude towards failures compared to others. It also provides some general implications for our understanding of entrepreneurial learning as an experiential process.