In this holiday edition, we explore what happens when someone refuses to accept the idea of a “lost cause” and instead gets down to the work of transforming a troubled life.

We hear the story of former executive, Mark Goldsmith, who was asked to volunteer as Principal for the Day at a New York City public high school. The self-described “wise guy” agreed but told organizers, “I want a really tough school.” So they sent him to Rikers Island, New York City’s largest jail. Goldsmith spent the day sharing with young inmates some of the lessons he’d learned in the world of business. “I created an analogy between General Motors and a drug cartel,” he explained. “And I showed them that the Kingpin who heads up the drug cartel is no different from the Chairman of the Board of General Motors.”

The students were enthralled by Goldsmith’s presentation and officials invited him to return the following year.  Goldsmith later formed Getting Out & Staying Out, a nonprofit that brings successful leaders to Rikers Island to speak with inmates. The organization encourages inmates to start planning for their release while they’re still in prison and provides a range of services to the young men once they’re released.

One of those men is Phillip Whyte, a 24-year-old former inmate who heard about Getting Out & Staying Out when he was serving time for a robbery conviction. Whyte, who was raised by a single mother, tells us that Goldsmith is a father figure to him now. “Even though I’m 24, I have way more learning to do,” he explains. “And sometimes you have to talk to a knowledgeable person who is successful in what they do.” Whyte will soon complete his Associate’s Degree and interns at the hip hop label Wu Tang Management.

Mark Goldsmith speaks to former inmates