In this episode of Uncorked: Wine, Business & Life, Bill Green and Jerrold Colton welcome legendary investor Ira Lubert to the Saddlehill Winery Tasting Room. Known as one of Philadelphia’s most iconic investors, Ira shares the incredible journey from winning a New Jersey state wrestling championship to becoming a contrarian investor who has raised over $17 billion and built a reputation for protecting the downside. He reflects on his deep ties to Penn State as an athlete, board chairman, and philanthropist, including his role in elevating the wrestling program to national dominance. From his early entrepreneurial days buying mobile homes to spearheading landmark investments like the Valley Forge Casino, Ira offers invaluable lessons on timing, luck, discipline, and daring to fail. A rare, candid conversation with a true heavyweight in business and life.