This podcast episode explores the journey of Bill Simmons, a sportswriter, as he navigates through various stages of his career. From his early struggles and the impact of Larry Bird and Magic Johnson on the NBA to his experience creating the Digital City Boston column and the rise of online sports writing, Simmons shares insights into the world of sports journalism. He also discusses the tension between objectivity and passion in sports reporting, his decision to expand his role at ESPN, and the inspiration behind creating Grantland, a multimedia website that revolutionized sports and pop culture coverage. The episode delves into the challenges and triumphs of starting The Ringer, including the transition from ESPN, the financial decisions made, and the eventual sale to Spotify. Simmons emphasizes the significance of continuous improvement and dedication while reflecting on the evolving role of management and the impact of technology on sports media.
