Entrepreneurial families experience partially severe conflicts among family members, often in connection with the role of the business in family communication. These conflicts threaten the continuation of the family business and peaceful family life. But, business families do not exist without context. They have a history and a cultural environment—both are influencing conflicts and conflict-management methods. In the present study, conflicts in Indian and German owning families are compared, always with a focus on distinctive historical and cultural developments. The direct comparison of these historically seen very different family systems offers owning families in both countries connecting factors to reflect upon known and possible new conflict management methods.