This dissertation explores risk preferences and career choice decisions amongst undergraduates and specifically addresses startup challenges facing students and universities. The first paper hypothesizes that undergraduate students from highly ranked universities have strong financial incentives (the "good job" trap) that lead them to pursue traditional, corporate careers immediately upon graduation. Analysis of 235 recent graduates from an Ivy League university and a Big Ten university, adjusted for monetary costs, parental preferences and individual ability, shows that the Ivy League graduates are in fact less likely to become entrepreneurs immediately upon graduation due to opportunity cost considerations. Students are also less likely to pursue an entrepreneurial career if they have multiple job offers and conversely, lack of quality job offers is a strong motivator for self-employment. The next paper introduces the concept of "losers' dilemma" and leverages a market driven, dynamic business simulation to specifically study how teams behave in a competitive setting, how they balance personal and team risk preferences, and how competitors can induce riskier behavior. Utilizing a sample of 130 undergraduates participating in a multiple 7-week dynamic simulations, we find that losing teams are dominated by risk averse individuals who avoid conflict, struggle aligning individual and team risk preferences, and claim to be risk takers but consistently showcase risk averse decision making. These losing teams display high confidence in their business projections but conversely, showcase low self-confidence and a "yo-yo" approach to strategy evolutions. Both papers not only contribute to entrepreneurship literature but also have practical implications for universities and startup incubators seeking to seed the next generation of entrepreneurs.