Darrell Silver is a successful entrepreneur who has founded and led several companies, including Thinkful, which he sold to Chegg. He holds a BA in Art History, Criticism and Conservation from Columbia University and has experience in education, technology, and finance. Silver has worked for Vail Resorts, Clinton Group, and Smarsh. He is also involved in charitable ventures, serving on the board of the Young Center for Immigrant Children's Rights. Currently, he is pursuing woodworking with his father.