I study the effects of (a) CEO power over the firm’s information and decisions and (b) CEO overconfidence about the firm’s underlying value on both firm’s equity financing and CEO personal stock trading decisions. I hypothesize that an overconfident CEO will reduce stock issues and increase stock repurchases. I also hypothesize that an overconfident CEO will reduce her own sales and increase her purchases of her firm’s stocks. Consistent with my hypothesis, I find that a CEO’s self-importance, her finance and technical education backgrounds and her assumption of multiple roles including the president and chairman titles significantly decrease her probability of issuing stocks. I also find that the firm’s recent performance, CEO’s finance and general education backgrounds and her assumption of multiple roles including the president title increase her probability of repurchasing stocks. I also consistently find that a CEO’s assumption of multiple roles and particularly the chairman title has a significant positive impact on her personal trades in stocks and hence her share ownership. This thesis highlights the relevance of a CEO’s traits for both the firm’s financing and her personal portfolio decisions.