Though the dark side of business-to-business relationships exists at both the firm and personal level, recent research evidence suggests that the theoretical conceptualization and empirical investigation concerning the latter is still under development. Building upon theoretical perspectives of organizational capability, organizational networking and social capital theories, this study investigates the boundary conditions of personalized business-to-business relationships (managerial ties) on business performance. Specifically formulated hypotheses are tested using the perceptions of senior executives in 137 Taiwanese firms operating in a variety of industrial sectors. Our study extends extant literature by revealing that the dark side of managerial ties is evident in the perceived management capability-political ties-performance and technology capability-business ties-performance interplays. More importantly our survey results are corroborated by evidence from interview results with twelve senior executives. Such findings collectively demonstrate the dark side of political ties (governmental interference in employment, blockage of information flow as well as conflicts of interest), and business ties (reciprocal obligations, time consuming factors and maintenance costs).