We examine how initial conditions shape entrepreneurs’ trust in venture capitalists (VCs) in early versus later stages of relationships. Based on stage theories of trust (Lewicki et al., 2006), we suggest that the basis of trust changes with relationship stage. Factors that impact trust in newly-formed relationships may differ in more mature relationships. Although trust can strengthen or dissipate over time (Meyerson et al. 1996), few studies have attempted to empirically test whether factors that aid or inhibit trust in early stages have the same effects in more mature relationships. Our purpose is to address this gap. Specifically, we examine how factors hypothesized to influence trust shape the top management team’s trust in VCs in newer versus older relationships. We examine two broad factors expected to influence entrepreneurs’ assessments of the investor trustworthiness early on: (1) VC’s reputation, and (2) the length and results of initial contract negotiations.