Many wealthy families hold all or most of their wealth in one highly appreciated security. Sometimes that stock represents a control position in a family company, but more often the holding has resulted from a sale of the family company for stock in a public company. If the sale occurred just prior to a bull market, the family may believe that owning one concentrated security is an excellent way to create significant wealth. This was certainly the case with many families who sold their companies in stock deals during the 1980s and 1990s. Unfortunately, periods like those two decades come along far less than once in a lifetime. The purpose of this white paper is to suggest a commonsense approach to dealing with large, concentrated stock positions, having in mind that there is a difference between a bull market and a sound investment strategy.