Watch Online Free on Watchseries. As Rick has gathered interviews for IT'S PITTSBURGH episodes over the last 2 seasons, he has often ended the conversation by asking, "Why do you live in Pittsburgh?" In this program, we edit together many of the responses, and we look at the Experienced Dreamers Contest that challenged entrepreneurs over 45 years of age to write about why they could bring their dream to Pittsburgh. It's an entertaining consideration of one of life's great questions.