For many entrepreneurs exit is not the end point of their entrepreneurial career path but rather the trigger to start a new venture (Wright et al., 1997). Despite the prevalence of entrepreneurial re-entry, there are hitherto scant insights into how the nature of prior start-up experiences influences ex-entrepreneurs’ likelihood of re-entry (Hsu et al., 2015). Furthermore, the few studies exploring re-entry intentions (Stam et al., 2008; Hessels et al., 2011; Nielsen & Sarasvathy, 2011) have focused on a limited number of individual characteristics, such as the entrepreneur’s education and experience, hereby however producing contradictory findings. The lack of conformity in prior work calls for a contingency approach, in which characteristics of the exited individual are studied in conjunction with characteristics of the exited venture. Hence, building upon self-efficacy theory, this study investigates the characteristics of both the exited entrepreneur and the exited firm as well as the relationship between these characteristics and the re-entry intentions of entrepreneurs at the moment of exit.