In this paper, we first develop an original theory in which, based on their individual skills and the quality of their business, entrepreneurs can keep their original business (and thus remain novice entrepreneurs), start and keep a new business in the same or another sector along their current business (therefore becoming portfolio entrepreneurs), transfer or shut their original business down to either start a new one (turning themselves into serial entrepreneurs), or enter the labor market as wage workers. We then use the insights from our theory to develop three main hypotheses that are finally tested for a 10-year panel dataset (2001 to 2010) of more than 4000 Vietnamese manufacturing firms. We estimate an occupational choice model and a survival model and find that (i) a greater endowment of human capital is associated with a higher likelihood of a business owner to become a serial or a portfolio entrepreneur; (ii) a higher quality of the new business is associated to a higher likelihood that it is run by any type of habitual entrepreneur. Particularly, high entrepreneurial skills together with a high-quality business positively influence the likelihood of an individual to be serial or portfolio entrepreneur; (iii) ceteris paribus, firms run by serial or portfolio entrepreneurs tend to stay in business longer, although high-quality ones run by novice entrepreneurs endowed with high entrepreneurial skills are those with the lowest probability to leave the market.