Andrea Ruma has worked for three years at Ruma's Fruit and Gift Basket (Ruma's), a 112- year- old family business in Massachusetts. Andrea is trying to decide whether she will stay in the business or leave to go back to teaching. The problem for Andrea is that her father, Jim Ruma, will not share any information on the company strategy, finances, estate planning, or succession planning, nor provide her with any feedback on whether she is doing a good job. Although Jim is 72 years old, he is an active and opportunistic businessman. In the last twenty years, he has gotten out of the wholesale fruit business and has entered five new business areas, all without any planning. Although the company is profitable and provides good income to four family members, Andrea has doubts as to whether she should commit to the company with the idea of possibly taking over the business as the only viable fourth generation family member.

The case focuses on succession planning for a successful family business that has reached a crossroads in which different family members have different stakes in the outcome of the business. The president of Goodwin Sporting Goods is 66 years old, has health concerns and is concerned about how to finance his retirement. He also has three children who rely on the business for financial support. He must make some tough decisions that will affect both the business and his family.