This paper examines post-communist managerial ethics during the emergence and transition of charismatic leadership in two privately owned media holdings in Russia and Kyrgyzstan. These media holdings were bootstrapped in the 1990s and 2000s by people without management experience and connections. This paper argues that Weberian charismatic leadership was a necessary leadership style to start a private business for people without links to elite networks. However, once firms establish themselves on the market, charisma fades and yields itself to a legal-rational leadership style. In particular, the paper compares and contrasts the managerial ethics issues arising from the loyalty-based leader–follower relations in the charismatic leadership phase and the legal-rational phase of a firm’s development and maturation. While the legal-rational phase brings positive changes to workload management and employees’ rights for vacation and p/maternity leave, task delegation remains an unsolved issue. Ambiguous career advancement criteria of the legal-rational phase replace rapid career progression of junior and middle managers during the charismatic phase. By examining the dynamics of managerial ethics transformation, this study adds to the literature on post-communist leadership, management and governance. Recommendations are provided for privately owned firms on how to advance managerial ethics to attract and retain qualified talent.