Grady graduated from Georgetown University with a BA in English and minors in international business, history, and studio art. A professional project manager, Grady worked on the production teams of the 2008 Papal Mass at Yankee Stadium, the Bravo series Long Way Round, the PBS series Texas Ranch House, and Michael Moore's documentary film SiCKO while living in New York City.

In April of 2010, Grady began an 18-month trip around-the-world, during which he visited 25 countries on 5 continents. Upon his return to the United States, Grady founded RETREET to redefine disaster relief and, through it, find purpose, community, and fulfillment for himself and others. Almost a decade into running RETREET, the organization merged with Keep America Beautiful, where it now is being taken to scale across a vast network of affiliates. Grady is an eagle scout, a 2015 graduate of Municipal Forestry Institute, the past-president of the Texas Urban Forestry Council, an at-large commissioner for the City of Dallas’ Arts & Culture Advisory Commission and the chair of the city’s Public Art Committee, and the president-elect of the Trinity River Audubon Center advisory board. Grady also is studying to become a certified arborist.