Karlyn Lothery earned a marketing degree and has worked in various communications roles, including as a news anchor and chief diversity officer. She is now the president of Lothery & Associates, which provides media training, executive communication coaching, and diversity training. Brian Cashman graduated from Catholic University and worked his way up from intern to general manager of the New York Yankees, despite never intending to work in baseball. He faces challenges such as fielding a winning team while dealing with New York media scrutiny.