This paper investigates empirically the relationship between various business portfolio properties (particularly technological properties) and chaebol′s performance using data on the 50 largest chaebols in Korea. In addition to the traditional indexes to measure diversification such as entropy index we calculated inter-industry technological similarity using R&D expenditure data by industry and 1990 Input-output Table in Korea, and obtained chaebol-level technological relatedness and internal transaction proportion from chaebols′business profile, inter-industry technological similarity and 1990 input-output table. We applied factor analysis on 13 business portfolio property indexes and showed that they could be grouped into 3 dimensions, diversification scope, inter-business relatedness and degree of vertical integration. In this paper, using 50 largest chaebols′financial data (1989-1994), we analyzed empirically the effect of business portfolio properties on ROS (Return On Sales) which is conventional index for firm performance and on TFP(Total Factor Productivity) growth which is a pure measure of firm performance. To utilize the advantage of panel data, FEM(Fixed Effect Model) and REM(Random Effect Model) were used. The empirical result shows that the entropy index as a measurement of inter-business relatedness is not significant but technological relatedness index is significant. OLS estimates on pooled data were considerably different from FEM or REM estimates on panel data. By introducing interaction effect among the three variables for business portfolio properties, we obtained three findings. First, only VI (Vertical integration) has a significant positive correlation with ROS. Second, when using TFP growth as an dependent variable, both TR(Technological Relatedness) and f[ are significant and positively related to the deepened variable. Third, the interaction term between TR and VI is significant and negatively affects TFP growth, meaning that TR and VI are substitutes. These results suggest strategic directions on restructuring business portfolio. As VI is increased, chaebols will get more profit. A higher level of either TR or W will increase TFP growth rate. but increase in both TR and VI will have a negative effect on TFP growth. To summarize, certain business portfolio properties such as VI and TR can be considered "resources" themselves since they can affect profit rate and productivity growth. VI and TR have a synergy effect of change in profit rate and productivity growth. VI increases ROS and productivity growth, while TR increases productivity growth representing a technological synergy effect.