Family businesses are everywhere: Literally from the corner grocery to the Ford dealership down the road, from everyday products in your home by S.C. Johnson to your next luxury vacation at a Marriott hotel, family businesses are the engines of not just the American economy, but of the world economy. And while they all face the challenges of any large or small business, e.g., profitability, market share, and employee management, they have additional challenges in that key employees are often related by blood or marriage. The multiple, overlapping relationships in a family business often create a level of emotional complexity that only people with training in complex systems and systemic family therapy can address. As if all this weren’t challenging enough, successful family enterprises that last multiple generations have another level of complexity: the evolution of the family and business over decades, sometimes centuries. This chapter presents the many facets of family business over time seen from the individual and family systems perspectives. While work exists that is focused on business succession, financial growth, legal strategies, and wealth management (Poza, Family business (4th Ed). Cengage Learning, 2013), this chapter deals with human factors including personal values, roles and character traits, and the intergenerational effects of significant capital on family and individual development. Examples of real, and fictional, family businesses are used to illustrate these issues as they play out over time.