Like every human, the sustainable entrepreneur is impacted by all the places they have inhabited, but even more so since their triple-bottom-line approach leads to a manifestation of their efforts in places. Opposing this concept of place, scholars describe the concept of placelessness as a manifestation of a lack of meaning or lack of physical location. This qualitative study of sustainable entrepreneurs explores the connection between sustainable entrepreneurship and place or placelessness.  Our approach opposes the common notion that placeness and placelessness are two separate boxes by saying that they are instead two extremes of a scale, making placeless or place-based within sustainable entrepreneurship a matter of degree rather than “either-or”. Building on Shrivastava & Kennelly’s framework of Location, Landscape, and Meaning, we were able to make contributions to the complex, multi-directional impacts that place(lessness) and the sustainable entrepreneur have on each other. While a connection to a place can also inspire sustainable behavior, it is the sustainable entrepreneurs’ environmental and social value creation that immensely benefits from the familiarity and security they experience in their place, as well as the communal support and trusting relationship with local institutions. Placelessness tends to offer stronger support mechanisms for the economic side of the venture, as well as, in the case of digital placelessness, flexibility, and a fast flow of knowledge. In return, the sustainable entrepreneur impacts their place context through their social and environmental efforts, as well as through community and place building.