Interview with Sheperd Doeleman, an astronomer at the Harvard Smithsonian Center for Astrophysics, founding member of the Black Hole Initiative, and founding director of the Event Horizon Telescope. He surveys his global initiatives and his interest in fostering black hole research in Africa and he describes how the pandemic has slowed down his work. Doeleman affirms that he is of the generation for which black holes were always “real” and not theoretical abstractions, and he provides a history of the discovery that supermassive black holes were at the center of galaxies. He reflects on the applied science that was achieved in the course of creating EHT, and he describes the unique values that land and space-based telescopes offer. Doeleman recounts his childhood in Oregon and his admission to Reed College when he was fifteen. He explains his motivations in completing a solo research mission in Antarctica and he describes the opportunities that led to his graduate research at MIT, where he worked with Alan Rogers at the Haystack Observatory on the 3mm VLBI. Doeleman narrates the technical advances that allowed his team to achieve an eight-fold increase in bandwidth, and he describes the EHT’s administrative origins and the events leading to the measurement of the Sagittarius A* black hole. He describes what it meant to image the black hole, and he conveys the deep care and caution that went into the analysis before EHT was ready to publicize its findings. Doeleman discusses winning the Breakthrough Prize as the public face of a large collaboration, and at the end of the interview, he considers the ways that EHT’s achievement can serve as a launchpad to future discovery.