In this paper, we extend the existing studies about serial entrepreneurship by analyzing whether the differences between serial and novice entrepreneurs could be attributed to the types of skills and competences possessed by the individuals, and whether particular motives for starting new ventures are more conducive to multiple businesses founding than others. We refer to the arguments of Casson (1982) and Lazear (2004) by suggesting that further selection of novice entrepreneurs into serial/habitual entrepreneurs may be a function of the levels of particular skills and competencies. In particular, we hypothesize that entrepreneurs with above-average levels of general skills are more likely to start multiple ventures whereas above-average levels of functional skills would have no noticeable (or have a negative) effect on the probability of becoming a serial entrepreneur. Prior literature has also suggested the importance of particular motives in the individual’s decision to pursue an entrepreneurial occupation. At the same time, relatively little is known about particular individual goals in the serial entrepreneurship context. We acknowledge the likelihood of differences in individual motives between novice and serial entrepreneurs while leaving the directionality of such differences to empirical investigation.