The span of a human lifetime is contained within its own generation, but we all develop an appreciation of our place in time marked by the history of the generations before us and the arrival of the generations after us. We are all transgenerational beings in that sense. This book presents a study of the experience of two generations engaged in business, the founders in one generation and the successors from the next generation. It places the family at the heart of the enquiry rather than questions of economic performance and growth. It shows how the family and the business impact upon each other; they are inextricably intertwined. It examines the dynamics of the family and their engagement in business over time, the intricate connections between and across two generations. This is a study of five families engaged in entrepreneurship, families in business, based in the north of England. It draws upon interviews from two generations in each of the families (see Table 1.1). Interviews were undertaken with members of the family from the generation that founded a business and family members who joined the business in the next generation. Each of the five families are designated as ‘intergenerational sets’ and named the Engineers, the Grocers, the Large Group, the Cheese Makers and the Insurance Brokers. With hindsight the term ‘interview’ seems inappropriately formal, and rather dull, in the light of the vivid experiences that I had listening to the participants tell me about their lives, their families and their businesses.