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For his Big Give, Trey chooses the Interfaith House in Chicago, an organization that provides residential care for homeless men and women in medical recovery. Not a minute can be wasted—he only has five days to raise as much money as possible. Within hours of leaving Harpo Studios, Trey has already assembled a team of friends to help him. "We definitely want to make the biggest impact that we can," he says.

Powered by adrenaline, Trey and his team work through the first night. "It was about 4:30 in the morning, and that was when the reality of what happened hit me," he says. "I pretty much lost it. I was on my bedroom floor, fetal positioned, balling my eyes out because at that moment I knew that my life is not going to be the same after this experience."

After dozens of calls, the first donation finally comes in—and it's just the beginning. Trey and his team decide to hold a fundraiser and are able to secure a room at Trump Tower in Chicago for the event. With time running out, the team manages to score big-ticket items for an auction—including a VIP outing event from the Chicago White Sox. The event raises an incredible $100,000 in just two hours!