Essays in entrepreneurial finance

In this dissertation, I study how the structure and conventions of the venture capital market affect the behavior of both investors and entrepreneurs. The venture capital market is characterized by high-risk investments with the potential for extreme rewards. The current structure and conventions of the market have developed at least in part to mitigate the level of risk faced by the investors. Characteristics of the market include convertible preferred securities, staged investment and board representation for investors among other features. In the first chapter of this dissertation, I study the effects of stage financing on effort provision and firm value, weighing the advantages of upfront financing against the incentive to misuse the capital for personal reasons. In the second chapter, I study how the use of convertible preferred securities and board representation affect the level of risk chosen by venture capital-backed firms. Both chapters primarily deal with the market structure as given, thus, the focus of this dissertation is on understanding the effects of the current market structure on real decision-making, rather than providing justification for observed conventions. In so doing, I uncover insights not previously available and meaningfully contribute to the existing literature. In the first chapter, I explore the optimal staging path for venture capital-backed companies. Staging investment allows a portion of the risk inherent to financing new ventures to be mitigated, as some portion of the needed funds can be withheld until after initial progress is realized. As a result, companies that show poor intermediate signals can be abandoned, saving investors from likely losses. Additionally, despite investors' representation on the board of directors, some misbehavior by the entrepreneur may not be preventable ex-post. Hence, there is value in limiting the amount of capital that the entrepreneur has access to while the firm is young and opaque, as this limits the amount that can be misused. These factors create a motive for stage financing. However, providing a larger amount of capital upfront can also provide flexibility and operational efficiencies that increase the potential value of the project. Weighing these effects against each other leads to an internal optimum level of staging, where some capital is provided upfront but a portion is withheld until further information is revealed and the firm matures. The entrepreneur's preferred level of capital raised initially exceeds the level that maximizes the value of the firm. I further explore how the solution changes when the entrepreneur disagrees with investors over the likely value of the project. Specifically, I study how the solution is affected when the entrepreneur is more optimistic about the distribution of project outcomes than are investors. This creates two separate effects that oppose each other. On one hand, optimistic entrepreneurs are less likely to misbehave and waste capital, lowering the cost of providing capital upfront and increasing the optimal amount raised initially. On the other hand, optimists believe that the price they can get for their equity will be higher in the future, increasing the perceived cost of upfront financing and decreasing its optimal level. I illustrate that in low information settings the former effect dominates while in high information settings the latter dominates. These findings provide insight into the staging decision not previously available. In Chapter 2 I focus on the incentives for risk-taking facing both entrepreneurs and investors. In venture capital financing, investors take convertible preferred stock which is senior to the common stock held by the entrepreneurs. Traditional economic logic would then imply that the entrepreneur has a stronger incentive for risk-taking than does the investor, by virtue of the security design. However, I show that this is not always the case. I explore how the incentives of the decision-making investors, the general partners of venture capital funds, are affected by the fact that they manage funds of other peoples money. Hence, their compensation profile is not linearly related to fund value. In particular, general partners are compensated with a mixture of fixed and performance sensitive income. I show that the performance sensitive component, carried interest, introduces a kink into the payoffs of the general partners which induces a preference for risky strategies in certain situations. My model predicts two key scenarios where, despite holding a senior security, general partners are more risk-seeking than entrepreneurs. First, general partners are risk-seeking late in the life cycle of their funds if prior performance has been poor. This is similar to the "gambling for resurrection'' effect in firms near default. Furthermore, in many cases, the possibility of future poor performance is sufficient to induce the GP to prefer high-risk strategies even early in the life of the fund, before intermediate progress has been realized. These findings are empirically relevant and shed light on which parties are the driving forces behind the level of risk selected by startup firms.

Keywords: Business.
Advisor: Strebulaev I. A. (Ilʹi͡a Alekseevich) 
Hodrick L. S. (Laurie Simon)
Pfleiderer Paul 
Zwiebel Jeffrey