Rich grew up in Springfield, Delaware County, and graduated from Cardinal O'Hara High School and Villanova University, Cum Laude. He earned a Juris Doctor from Villanova University School of Law. Rich started his career in New York City in the Capital Markets group of Price Waterhouse. He practiced law as a commercial litigator at Kittredge, Donley in Philadelphia and at Baker & McKenzie, Brown & Winfield, and Ropes & Majeski in Los Angeles. Rich left the practice of law to conceive and craft the strategy for, and manage, his brother Joe's initial political campaign. Rich was then the Southeastern Pennsylvania Political and Field Director for the Hillary Clinton for President campaign. Rich was named one of the Top Democratic Influencers in Pennsylvania by Politics Magazine, and his brother credited him as the reason why his upset victories were achieved. Rich worked for the Los Angeles Olympic Organizing Committee and was an exceptional professional triathlete who was selected to the U.S. National Triathlon Team for the World Championships. Rich was devoted to his close-knit family of six sisters (Kathleen, Barbara, Ann, Elizabeth, Margaret, and Patricia) and one brother (Joe), and his wonderful now-departed father, Captain Joseph Sestak, U.S. Navy, and loving mother, Kathleen (Kay) Sestak.