This research applies Max Weber’s theory of charismatic authority to the leaders of media companies and explores the origins and dynamics of media leadership in Russia and Kyrgyzstan in 1991–2016. Two case studies of leaders of financially viable privately-owned media businesses—Abak-Press in Russia and Computer Press Kyrgyzstan—are compared and contrasted. Abak-Press’s Alexei Kharitonov and Computer Press’s Kylychbek Sultanov founded their media companies after the fall of the Soviet Union having no prior management expertise and grew them from small “one-man army” businesses into self-reliant media holdings. Based on qualitative data from 54 interviews with leaders themselves, company employees, competitors and industry experts, the paper argues that charismatic leadership helped these firms grow and become financially sustainable. As charisma is eventually routinized, the charismatic authority of two given leaders is transforming into a legal-rational authority or the authority of managers. This process is influenced by specificity of media market dynamics. This research contributes to the theoretical framework on media entrepreneurship and media leadership in the post-Soviet space.