In this paper, we aim to investigate how venture characteristics and investors’ individual differences influence investors’ evaluation preference towards novel and imitative ventures. Current findings suggest the innovativeness of business model (BM) (Kollmann & Kuckertz, 2010), and the leadingtime in the market (Shepherd et al., 2000), are important factors for new ventures to achieve positive evaluation from investors. However, novel ventures are not the only type of ventures receiving investment. Business model copycats (BMCs) — ventures trying to pursue business opportunities by purposefully imitating leading business models — are becoming increasingly popular and influential. Yet, current theory of investors’ decision-making does not offer adequate explanation about when and why innovative and pioneering ventures are actually more or less attractive to fund than imitative ventures. To address this theoretical shortcoming, we draw upon theories of strategic imitation (Lieberman & Asaba, 2006) and cognitive perspective on entrepreneurial decision-making (Grégoire, Corbett, & McMullen, 2011; Schwenk, 1988) to build our arguments about conditions influencing investors’ evaluation preference.