Despite growing research interest in family businesses, little is known about the characteristics of the families engaging in them. The present paper uses Olson’s (Journal of Psychotherapy & the Family, 1988, 4(12), 7–49; Journal of Family Therapy, 2000, 22, 144–167) Circumplex Model of Marital and Family Systems to look at first-generation family firms. We describe existing typologies of family businesses and discuss similarities between the characteristics of first-generation family firms and the rigidly enmeshed family type described in the Circumplex Model. The Steinberg family business (Gibbon & Hadekel (1990) Steinberg: The breakup of a family empire. ON, Canada: MacMillan) serves to illustrate the difficulties of rigidly enmeshed first-generation family firms. Implications for understanding troubled family businesses are discussed together with guidelines for the assessment of a family business in crisis and for intervention: enhancing open communication; allowing for more flexible leadership style, roles, and rules; and maintaining a balance between togetherness and separateness.