Radio B92 was an iconic independent media institution in Serbia. Founded in 1989, B92 provided Belgrade listeners with subversive rock music, high-quality journalism, and independent perspectives on politics in the former Yugoslavia. An early adapter to the internet, B92 has been credited with sparking the many demonstrations that took place in Belgrade during the 1990s. While the role of Radio B92 during the turbulent days of the Yugoslav Wars is well known, less known is the role of its first CEO and news director in the creation of what would become the Media Development Investment Fund (MDIF). Drawing on semi-structured interviews with journalists, scholars, funders, diplomats, and media observers conducted in Belgrade in 2022, this study argues that much can be learned from the case of Radio B92 and the short history of independent media in Serbia. Although B92 ultimately met a tragic death at the hands of privatization and “market censorship,” the “impact investment” model of media development it sparked lives on. Combining affordable loan and equity financing with technical assistance and advisory services, MDIF’s model helps struggling news organizations avoid dependency on grants. Although the 2022 reelection of President Aleksandar Vučić demonstrates his party’s successful state capture of Serbian news media, a look back at the case of Radio B92 has implications for the broader question of what works in international media assistance and why.