Trust is recognized to be a core driver of effective cooperation between two parties (Dawes, 1980; Keren & Raub, 1993; Komorita, Hilty, & Parks, 1991). This also applies for cooperative relationships between entrepreneurs and investors (Shepherd & Zacharakis, 2001), which are an important condition for venture success (Cable & Shane, 1997; Timmons & Bygrave, 1986). Thus, understanding antecedents of trust helps foster cooperation and ultimately venture success. Until now, few entrepreneurship studies tackled trust directly and empirically (Welter & Smallbone, 2006). Two recent studies mark an exception by looking at antecedents of entrepreneurs’ trust in their investor that are rooted prior to the investment (Stratling, Wijbenga, & Dietz, 2011; Welpe, 2008). In adopting a post-investment perspective we extend this research into the phase where entrepreneur-investor cooperation materializes. Using the prisoner’s dilemma lens we develop a fresh perspective on antecedents of trust and show that factors of perceived trustworthiness (ability, benevolence, integrity) and procedural justice impact entrepreneurs’ trust in their investor.