This study elucidates the mixed gamble confronting family firms when considering a related firm acquisition. The socioemotional and financial wealth trade-off associated with related firm acquisitions as well as their long-term horizon turns family firms more likely to undertake a related acquisition than nonfamily firms, especially when they are performing above their aspiration level. Postmerger performance pattern confirms that family firms are able to create long-term value through these acquisitions, and by doing so, they surpass nonfamily firms. These findings stand in contrast to commonly used behavioral agency predictions but can be reconciled with theory through a mixed gamble lens.