Serial entrepreneurial endeavors may not be consecutive. Empirical evidence showed that a significant number of serial entrepreneurs were employed just before they reentered entrepreneurship (Westhead & Wright, 1998; Amaral et al., 2011). This paper thus aims to examine whether and how this intervening employment experience makes a difference in the relationship between prior entrepreneurial experience and intention to reenter entrepreneurship. Drawing on Schneider’s (1987) attraction-selection-attrition (ASA) theory, we argue that when entrepreneurs exit their ventures and start to work on an employment job in an organization, their prior entrepreneurial experience would hamper their socialization within the organization, which in turn increases their intentions to leave the organization to start another venture (i.e., selection to attrition). This relationship, moreover, would be altered by the organizational context such as organizational structure (Covin & Slevin, 2006).