This dissertation explores how industry incumbents use corporate venture capital (CVC) to achieve strategic objectives and identifies multiple dilemmas and challenges associated with the investments. In each of the three essays in the dissertation, I extend the perspective beyond the traditional dyadic view on CVC investments and examine how different parties and institutional environments could affect CVC investments. The first essay explores the dilemma that CVC investors face when investing in entrepreneurial ventures that develop substitutive technologies. The findings suggest that on average, incumbents are less likely to invest in substitutive versus complementary ventures. However, under industry-wide pressures, syndication with industry competitors could help them mitigate the concerns associated with such investments. The second essay explores the dilemma that CVC investors face when investing in spinouts of other industry incumbents due to the conflict of learning benefits versus competitive risks involved with the investments. The findings suggest that the competitive risks discourage CVCs’ investments in other incumbents’ spinouts, but this affect is attenuated when there are substantial learning benefits associated with the investments. The third essay explores the dilemma that CVC investors face when external institutional demands conflict with internal efficiency. The findings suggest that when faced with legitimacy challenges, incumbents could use CVC investments as an impression management mechanism to address external demands. In addition, firms that have a greater gap between what they are 'expected to do' versus what they are ‘actually doing’ are more likely to make such investments, particularly if the ventures' industry segments are more compatible with their own. Through the three essays, I aim to contribute to the literature on CVC investments by expanding the perspective beyond the CVC investor-investee dyad and examining underexplored assumptions and dilemmas in the CVC literature, ultimately extending our understanding on how CVC investments could be strategically utilized by industry incumbents.