This paper builds on 15 interviews with media owners and editors-in-chief of Russian digital media businesses. The interviews took place in Moscow, Saint-Petersburg, Ekaterinburg, Barnaul and London between 2015- 2017. This paper offers detailed reflections on doing qualitative research into media firms' organisational change management in developing markets such as Russia. The paper analysed how building trust with gatekeeprs and later with interviewees impacts different stages of the interview process: pre-interview, actual interview and post-interview. The paper argues that diverse and fluid interview-based research process within the emerging digital media firms is shaped by time and data constraints as much as it is by the social backgrounds of the involved parties. It is particularly acute for researching media in transitioning, post-socialist cultures where the social and economic class structures are still being shaped. Additional recommendations are offered for qualitative researchers of media businesses on managing comprehensive qualitative data sets.