Jay Love is a charity sector titan whose profound influence spans four decades and counting. He has developed and led a succession of major software firms serving the nonprofit fundraising world, beginning with Master Software in the 80s, eTapestry at the turn of the century, and Bloomerang starting in 2012. In each case, he identified a problem bedeviling nonprofits, pioneered a solution, and then was a key figure in transforming the way organizations build relationships with supporters. Today he continues in that work, serving as Chief Relationship Officer at Bloomerang while advising a rising generation of social good tech pioneers. We begin this conversation by hearing about his Indiana roots, the field of dreams he and his brothers built, and his first encounters with philanthropy as chauffeur to one of his college community’s major donors.