Venture Capitalists (VCs) practice investment activities for financing potential startups with innovative ideas. This paper initially addresses the investment process including five consecutive stages of business plan origination, screening, evaluation, negotiating investment and financing with assistance. Thereafter it identifies the challenges faced by VCs over their investment decision diving into pre and post investment segments taking consideration of potential biases and moral hazard. Finally, to offset such challenges by heuristics, three sophisticated methods-verbal protocol analysis, conjoint analysis, and actuarial decision model are generated for VCs to spur entrepreneurs by profitable investment. The consequences of the study are helpful for VCs in their investment decision-making process to amplify their prosperity rate.