Previous literature has highlighted that habitual entrepreneurship can signal higher levels of “entrepreneurial human capital” (Westhead et al. , 2005). Our main goal is to explore the determinants of the decision that separates entrepreneurs who leave their first business and do not re-enter entrepreneurship (novice) from entrepreneurs who leave their first business and re-enter entrepreneurship (serial entrepreneurs). Our study uses a longitudinal matched employer-employee data set to examine the relationship between the entrepreneurial human capital, organizational and environmental variables, including the mode of exit from the first firm, and the decision to re-enter entrepreneurship. We distinguish between serial entrepreneurs who switch directly into a second entrepreneurial experience after exiting the first one, and serial entrepreneurs who experience a different labor market status (paid-employment, non-employment) in-between the first and second entrepreneurial experiences, and may therefore be deemed latent, or even nascent serial entrepreneurs. A discrete choice model, similar to those proposed by Evans and Jovanovic (1989), and Taylor (1996) is used in our analysis.