Career mobility implies consecutive decisions by individuals on being or not being employed in the labor market. Intrapreneurial experience seems to inspire individuals for becoming entrepreneurs. Guerrero and Peña-Legazkue (2013) define intrapreneurial experience as a human capital attribute of employees who have a leading role in the development and implementation of re-generation activities within an organization under a proactive, innovative, and risk-oriented focus. Conventional wisdom also suggests that individuals’ age is another influential factor of entrepreneurship (Parker, 2009). However, little is known on how the probability of re-engagement into “serial” entrepreneurship evolves with age, how similar (or dissimilar) is such a probability for different types of entrepreneurship (i.e., necessity and opportunity driven entrepreneurship) and how the intrapreneurial experience accumulated by individualsaffect the choice of re-engagement into entrepreneurship. To further explore this complex issue, we draw upon both the Douglas– Shepherd model (2002) and Kautonen et al. (2014) model and test the effect of entrepreneurial and intrapreneurial experiences on individuals’ engagement into serial entrepreneurship as they age.