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This case describes a series of three vignettes confronted by a fast-growing extended warranty services company, Extended Service Plans of America (ESPA). Doug Tudor had become the company''s President after completing its acquisition for Asurion Corporation in June 2006, after a two-year search and negotiation process. Ninety-four days later, three situations occur simultaneously: (1) one of Tudor''s two top managers improperly leaks confidential information to the company''s former owners; (2) a terminated employee threatens to badmouth the company to its highest-profile customer; and (3) new information regarding a vice-president''s drinking and performance problems seems to call for urgent action. Allows students to understand how to deal with typical issues faced by small companies, including the dynamics of family-owned businesses, barriers faced when trying to professionalize management, and challenges faced by a new manager trying to build credibility in such an environment. Students are asked to role-play and resolve the 3 issues, and to cite best practices for handling such types of management situations.