Corporate insiders frequently borrow from lending institutions and pledge personal equity shares as collateral for the loan. Using manually collected pledge data for January 2007-December 2011, I examine how this phenomena affects firm investors and analyze agency conflicts between pledging managers and (a) outside shareholders, and (b) bondholders. Pledging potentially influences investor risk through changing managerial incentives and/or contingency risk from ill-timed margin calls. Findings suggest influential insiders extract private benefits of control at the expense of outside shareholders through pledging. Difference-in-differences regressions utilizing an exogenous shock to lending supply indicate pledging corresponds with a 9.9% relative increase in stock volatility – controlling for changes in fundamentals – and support a causal interpretation of the relation between pledging and equity risk. Despite apparently harming equity investors however, further analysis suggests pledging benefits bondholders, and corresponds with an economically and statistically significant reduction in yield spreads on corporate bonds. Robustness tests evidence reductions in risky financing when insiders pledge, corroborating the negative relation between pledging and cost of debt and consistent with mitigated agency conflicts between managers and bondholders. / Business Administration/Finance