We investigate the problem of a firm wishing to finance a project by issuing securities under asymmetric information. We find that, when outside investors can produce (noisy) information on the firm's quality, the degree of information asymmetry resulting in equilibrium is endogenous and depends on the information sensitivity of the security issued. Thus, in contrast to the prediction of the pecking order theory (see, e.g. Myers and Majluf, J. Financial Econom. 13 (1984) 187) a security with low sensitivity to private information, such as debt, does not always dominate one with high information sensitivity, such as equity. A firm's preference for equity rather than debt depends on the costs of information production, the precision of the information-production technology, and the extent of the information asymmetry. We also study the optimal security design problem and find that, depending on the cost and precision of the information-production technology, risky debt or a composite security with a convex payoff emerges as optimal securities.

This paper examines the strategic role of high levels of debt and bankruptcy threats in deterring entry into monopolistic markets. In the context of an infinite horizon entry game, we show that if a potential entrant has access to debt financing with limited liability, the unique sub-game perfect equilibrium involves the entrant successfully issuing a high level of debt, entering the market and being met with cooperation. If, in addition to the entrant, the incumbent also has access to debt with limited liability, it will be highly levered and will completely pre-empt any entry in equilibrium. Finally, if the incumbent faces a variety of potential entrants with differing abilities to capture market shares, its optimal capital structure will help pre-empt the entry of the tougher entrants, while allowing the weaker ones to share the market. The results of extreme leverage are also shown to hold in an alternative formulation analyzed by Kreps and Wilson (1982) and Milgrom and Roberts (1982), and thus are robust to model specifications. The empirical implications and possible application to high leverage industries are briefly discussed.

We analyze firms’ choice of exchange to list equity and exchanges’ choice of listing standards when insiders have private information about firm value, but outsiders can produce (noisy) information at a cost. Exchanges are populated by two kinds of investors, whose numbers vary across exchanges: sophisticated (low information production cost) investors and ordinary (high–cost) investors. While firms are short-lived, exchanges are long-lived, value-maximizing agents whose listing and disclosure standards evolve over time. The listing standards chosen by exchanges affect their “reputation,” since outsiders can partially infer the rigor of these standards from the post-listing performance of firms. We show that, while exchanges use their listing standards as a tool in competing for listings with other exchanges, this will not necessarily lead to a “race to the bottom” in listing standards. Further, a merger between two exchanges may result in a higher listing standard for the combined exchange relative to that of either of the merging exchanges. We develop several other implications for firms’ listing choices and resulting valuation effects, the impact of competition and co-operation among exchanges on listing standards, and the optimal regulation of exchanges.