The body of this dissertation consists of three papers: Chapters Two, Three, and Four. The first of these analyzes direct financial contracting between the manger of a firm and investors when it is costly to verify firm output. First, an extension of Townsend\u27s (1979) result is obtained, enabling us to characterize optimal contracts when agents may be risk averse. Then it is shown that the use of the same contract for multiple identical investors is always dominated by asymmetric contracts in which some investors take subordinated positions involving more monitoring and higher returns in non-verified states. The model offers an explanation for the existence of multiple classes of securities even in the absence of taxes. Chapter Three exa...