In 2002, Ashley Capps took a gamble- he rented hundreds of acres in rural Tennessee and put on a music festival. Coming on the heels of the infamous Lollapalooza '99 and an unsuccessful festival at the same site two years earlier, few thought Ashley could pull it off. As you (and the 80,000 people who attended the festival this year) know, Ashley and his partners proved the doubters wrong and created one of the most iconic festivals in modern America.

Bob and Ben caught up with Ashley Capps back stage at Bonnaroo to talk about the history of Bonnaroo, how Ashley selected Manchester, TN, and the changes in the live music industry that have happened since he began working in live music decades ago. He also shares his insight on building the relationships that make a major festival sustainable. Bob also shares his experiences playing Bonnaroo with the Avett Brothers from the small stage in 2006 to the main stage in 2019.

The Road to Now is part of the Osiris Podcast Network. This episode was edited by Gary Fletcher.