This paper aims to present a study of the role of prior start-up experience as a source of learning in the entrepreneurial process. Three learning outcomes are examined with respect to a comparison between habitual and novice entrepreneurs: skills for coping with liabilities of newness, preference for effectual reasoning, and attitudes towards failure. This is an empirical study based on statistical analysis conducted on a sample of 231 Swedish entrepreneurs that have started a new independent firm in 2004. The findings suggest that habitual and novice entrepreneurs differ significantly with regard to several interesting aspects of the hypothesized dimensions. The findings provide a better understanding of start-up experience as a source of learning and its effects on the skills, preferences and attitudes of habitual entrepreneurs. Previous research has suggested that prior start-up experience is an important source of entrepreneurial learning, but has not put much effort into explaining how this particular type of experience influences various learning outcomes on an individual level. The present study advances these suggestions by showing how prior start-up experience influences entrepreneurs' skills for coping with liabilities of newness, effectual reasoning and attitudes towards failures. Moreover, the study contributes to existing literature and research on entrepreneurial learning by developing explorative measures of individual learning outcomes that have been highlighted as influenced by prior experience in recent entrepreneurship research.