In my first chapter, we document and study the use of Rule 10b5 1 preset repurchase plans. We exploit this new and widespread form of payout to examine an issue at the core of payout decisions—the tradeoff between commitment and financial flexibility. Relative to open market repurchases, preset plans provide an expanded repurchase window and increased legal cover, albeit at the cost of reducing repurchase flexibility and the option to time repurchases. These costs and benefits are significantly associated with Rule 10b5-1 adoption. Consistent with preset plans signaling commitment, Rule 10b5-1 repurchase announcements are associated with greater and faster completion rates, with more positive market reactions, and with more dividend substitution than open market repurchases. Lastly, we find that preset repurchase plans represent a unique payout tool whose introduction encouraged a different set of firms to buy back stock and significantly altered the payout landscape. My second chapter examines the strategic use and timing of share repurchases by insiders for personal gain. Using grant level compensation data and a hand-collected sample of monthly repurchases, I find a positive relation between CEO equity sales and share repurchases. I identify the relationship by instrumenting equity sales with equity grant vesting schedules. This relation is persistent across firm characteristics and does not appear to be destroying shareholder value. The results indicate managerial self-interest motivates a subset of share repurchases.