Family businesses are critical to the development of any nation’s economy based on their potential to generate employment, develop local technology, and develop indigenous entrepreneurs. Family businesses also survive for relatively longer period compared to any other business. This paper therefore examined the nature of family businesses and the willingness of graduates to take up family businesses in Southwestern Nigeria. The paper elicited information from primary data. The study population consisted of all the National Youth Corps members that served in Southwestern Nigeria in the 2016/2017 set. Three states from the six in the region were randomly selected namely Osun state, Oyo state and Ekiti. An average of 2,000 Corps members were being posted to each state for a batch. There were usually three batches A, B, and C consisting of two streams 1 and 2 respectively in the Southwestern Nigeria. A purposeful sampling technique was used to select three hundred (300) respondents from the three states based on those who had family businesses. Findings revealed that more than half (59%) of the family businesses were into trading, while 21% were involved in production and 20% were into service businesses. The result also showed that 79% of the graduates were willing to take up their family businesses, while 21% were unwilling. Two factors were found to be significantly responsible for graduates’ decision in respect of taking up or not taking up family business. These were inaccessibility of fund (t= 9. 105; p<0.05) and lack of technical expertise/know how (t = 5.447; p<0.05). The paper concluded that availability of fund (46.9%), technical know-how (30.3%), and government policies (13%) were critical factors stimulating graduates’ willingness in succeeding family business.