Trans-generational entrepreneurship is the key to the succession and growth of family businesses. It involves resource orchestration between two generations and innovation in succession processes. Recent researches have paid much attention to the effects of idiosyncratic resources in family businesses on entrepreneurship without noticing the resource heterogeneity between incumbents and successors as well as the dynamic changes of resource structure during the succession processes. Resource orchestration between two generations provides the resource base and dynamic for portfolio entrepreneurship. The generational involvement brings the heterogeneous resource base while resource bundling between two generations provides the dynamics for portfolio entrepreneurship. Based on RBV, this paper studies the influence of trans-generational resource heterogeneity and bundling on the behaviors of family business entrepreneurship. By using the data of public family business successions in China during 1999 － 2012 and regression analysis, the following conclusions are obtained. First, when the knowledge base and personal values between two generations are heterogeneous, firms tend to involve in portfolio entrepreneurship. Second, resource orchestration between two generations makes family businesses more inclined to involve in portfolio entrepreneurship. Third, market liberalization level has a negative effect on the relationship between resource heterogeneity and portfolio entrepreneurship. This study contributes to the implication of resource based view and resource management perspective in the family business field and researches on portfolio entrepreneurship in a transitional economy.