There, the 2002 graduate found himself working in the team's corporate affairs group at the same time a lanky, sixth-round draft pick named Tom Brady was ascending to the top of the NFL. As a freshman at Boston College, the younger McDonough started working for the Patriots, and after graduation joined the organization full-time. He made it to Fenway that day, and ended up working at the radio station on its promotions team, eventually setting up microphones and running wires for a famous Boston Globe sports reporter, who also happened to be named Will McDonough.
“I didn’t want to tell them I didn’t have my license,” he said. At 16 years old, he showed up on his first day and was asked to drive the company van down Boylston Street to Fenway Park and hand out flyers. As a sophomore at Westwood High School in suburban Boston he landed a gig at local sports radio station WEEI. McDonough, who looks and sounds like a distant Kennedy relative, was a sports buff as a boy. That may all change if his gamble with iCash pays off. In past interviews, the questions were often about his former bosses, the New England Patriots' star quarterback Tom Brady or former Goldman Sachs president Gary Cohn. McDonough is not used to talking about himself. He joins a growing list of Wall Street alumni who have left the perceived safety of places like Goldman for the new frontier of technology known as the blockchain. It's also backed by Goldman Sachs alum Matthew Goetz's crypto hedge fund BlockTower. Already, iCash has attracted investments from the 1Confirmation Fund backed by Peter Thiel, Marc Andresssen and Mark Cuban. Now 38 years old, McDonough is taking center stage, leading his startup, iCash, through an initial coin offering that launched in mid-July. “It’s still not lost on me how pretty damn cool that is,” McDonough said in a recent interview. For an up-and-comer named Will McDonough, who now calls some of those men “brothers,” it helped get him hired as a rookie with a lackluster finance resume at some of the most respected firms on Wall Street.