This article argues that to capture Russia’s influence abroad, one needs to comprehend the country’s “gray diplomacy” as a neoliberal realm open to individual initiatives. We define “entrepreneurs of influence” as people who invest their own money or social capital to build influence abroad in hopes of being rewarded by the Kremlin . We test this notion by looking at both famous and unknown entrepreneurs of influence and their digital activities. We divide them into three broad categories based on their degree of proximity to the authorities: the tycoons (Yevgeny Prigozhin and Konstantin Malofeev), the timeservers (Alexander Yonov and Alexander Malkevich), and the frontline pioneers (the Belgian Luc Michel). An analysis of the technical data documenting their online activities shows that some of these initiatives, while inscribed into Moscow’s broad aspirations to great powerness, are based on the specific agendas of their promoters, and thus outlines the inherent limits of Moscow’s endeavors.