Entrepreneurial turns, serendipitous events, entrepreneurial skills and values are critical to the success of rural SMEs. Likewise, ‘Resource Orchestration’ is an important element of strategic, entrepreneurial activities. An analysis of a case study of a rural family farm business in Italy is provided demonstrating an innovative model of ‘rural entrepreneurship’ focused on farm diversification to valorise full employment of family members and increased productivity as a direct response to rural policy. The analysis shows how collective family entrepreneurship can exploit ‘clusters of opportunities’ through updating entrepreneurial skills. ‘Serendipitous acts’ are integrated into localised diversification strategies.