Business Angels (BAs) face uncertainties in their investment decision, not only regarding the environment but also about actors’ ability and willingness to perform as promised (behavioral uncertainty). This study focuses on behavioral uncertainties arising from the BAs’ relationship with the entrepreneur in the investment decision process, and investigates (1) how BAs perceive behavioral uncertainties towards entrepreneurs in the investment decision process, (2) which approaches they apply in collecting information, (3) how these approaches build on the confidence and trust, and (4) how confidence and trust impact the final investment decision.