Few studies have explicitly focused on risky group decision making in information sharing or examined the manifestation of communication differences in face-to-face (FTF) and computer-mediated communication (CMC) teams. Hypothesizing that information-sharing behaviors could be influenced not only by contextual forces but also by personality and trust, we integrate communication mode, trust and personality into a theoretical framework, and also examine the possible impact of these constructs on risky group decision-making outcomes. Our interdisciplinary study integrates the fields of information system management, investment analysis and financial education by examining both FTF and CMC teamwork in a Stock-Trak portfolio simulation. We find that contrary to the common wisdom, even though FTF team members tend to feel greater levels of trust, affiliation and satisfaction in their team collaboration process, CMC teams eventually outperform their FTF counterparts by having greater portfolio returns and investor utilities.