We draw upon the mixed gamble perspective to investigate the entry timing decisions made by family firms in the context of cross-border acquisition (CBA) waves. We argue that family-controlled firms trade-off short-term SEW and financial losses in favor of long-term SEW and financial gains, while moving early in CBA waves. Findings suggest that family-controlled firms have a higher preference for early movement compared with nonfamily-controlled firms. Further, we show that founder’s presence on the board and acquirer’s superior performance amplifies the mixed gamble trade-offs, thereby strengthening the relationship between family control and early movement within CBA waves.