Cashman has referred to himself as an "adrenaline junkie." In December 2010, Cashman rappelled from a building in Stamford, Connecticut as part of an annual Stamford Christmas celebration. He jumped from an airplane with members of the United States Army Parachute Team to raise awareness for the Wounded Warrior Project and broke his right fibula and dislocated his right ankle in the process. In November 2014, Cashman slept on a New York City sidewalk to raise awareness on behalf of homeless youth.
