Writer, producer and podcast pioneer Bill Simmons is a man whose life, career and worldview have changed in real time with the evolution of Internet. Bill talks with Marc about some of the checkpoints in that evolution, including why he walked away from a big break in TV when he was writing for Jimmy Kimmel, why he thinks he was considered ‘difficult’ at ESPN, and why his HBO show wasn’t what he thought it would be. They also talk about Magic Johnson, Grantland, Letterman, divorce, documentaries, and Andre The Giant. This episode is sponsored by Comedy Central, Squarespace, and Casper.