Swedish financier, philanthropist, and progressive Olof Aschberg played a dynamic, but "forgotten"role in the contacts between international labor, Western finance, and Soviet power across the world wars. We first suggest Aschberg can be studied as a converter of different forms of capital as well as a trader in trust in between the practices of diplomacy and entrepreneurship. We then outline Aschberg's wide-ranging activities drawing upon existing secondary literature in lieu of a more systematic study of his life. Third, we concentrate on his interwar solidarity work and anti-fascism based in Paris. We analyze, fourth, his cultural diplomacy and publishing activities out of New York in between the Second World War and the early Cold War. Finally, we argue that Aschberg's multi-positional and variegated vita illustrates the merit of employing entrepreneurship, in its most broad sense, as an analytical category for investigating the art and practice of citizen diplomacy.