This thesis proposes three studies that provide novel empirical evidence on how different types of VCs' characteristics signal the quality of an entrepreneurial venture and influence investment strategies of funds subject to self-regulation. In the first study we aim at contributing to the ongoing debate on the different effects of reputation and status on organizational outcomes. We explore the signaling value that these two organizational attributes exert on external parties judging the quality of entrepreneurial ventures under uncertainty. Moreover, we examine whether signaling mechanisms are valuable only if the external parties are affected by high information asymmetry with the valued venture. We test our hypotheses using a sample of 1,339 U.S. clean technology ventures that received the first round of Venture Capital (VC) between the years 1990 and 2012. We look at their ability to gather supplemental financial resources for survival and growth by completing an Initial Public Offering (IPO) or an acquisition by an incumbent firm. The findings indicate that VCs' reputation - an economic attribute based on past performance - can signal a venture's quality externally, while VCs' status - a social-standing attribute - does not have signaling value. The results also show that quality signals are more relevant for public investors at IPOs than for managers of acquiring companies. The second study looks at how inter-organizational ties with reputable VCs affect valuations received by entrepreneurial ventures that go public. I propose that the signaling effect of reputable VC ties is lower when there is misalignment of strategic interests between the venture and the VCs. I consider the amount of shares sold by insiders in the initial public offering (IPO) and investors' enforcement of demand registration rights as elements indicating misalignment of interests with the venture. The hypotheses are tested on using a sample of 86 IPOs in the main U.S. stock exchanges completed by entrepreneurial ventures operating in the Clean Technology sector. The results suggest that affiliation with reputable VCs elicits a positive response by public investors. However, public markets react less favorably to ties with reputable VCs when they sell large amount of their shares in the IPO or resort to demand registration rights to force the public offering of their shares. The third study investigates organizations' use of self-regulation as form of symbolic response to normative pressure that does not necessarily entail compliance in practices. I argue that, when self-regulatory initiatives are not supported by an explicit regulatory environment, opportunistic organizations might reduce their efforts to align with the normative ideals through compliant actions and behaviors. The "walking of the talk", which is the implementation of actions that are aligned with the symbolic response, might also be discouraged by alternative means to obtain organizational legitimacy, such as through an organization's status. The hypotheses are tested on a sample of Venture Capital (VC) funds whose limited or general partners voluntarily decided to join the United Nations' Principles of Responsible Investment (UNPRI, 2006) initiative between 2006 and 2014. The results from a difference-in-differences estimation show that VC funds' likelihood to invest in clean technology companies is lower after funds' stakeholders (i.e. general or limited partners) join the UNPRI initiative. I also find that the likelihood to invest in clean technologies after self-regulation is negatively moderated by the VC fund's status.