This study seeks to bridge the gap between education and practice by conducting qualitative research with hiring managers at legacy media companies. Semi-structured, in-depth interviews were conducted with 15 media managers on the East and West coasts of the United States to understand how to prepare students for a dynamic media industry. The study identified themes related to experience, resume writing, successful interning, showing passion, interviewing, self-branding, and advice for educators. It is recommended that educators and media programs provide students with a broad overview of the media landscape, more skills-based classes, and a strong connection to the industry.