The girls interview the inimitable Holly Gleason, a universally respected journalist, music critic, author, artist development consultant, songwriter, and beloved friend of the music community.   Subjects for this episode include:

- Introducing Holly
- Writing with Kenny Chesney
- Honoring Nashville’s writing legacy
- Superstars who are humble
- How Holly met Kenny
- Growing up playing golf
- Meeting Vince gill
- Interviewing Neil Young
- The first Farm Aid
- Getting Chesney wrong
- Interviewing Lou Reed
- Steve Earl and Cowboy Junkies
- Four archetypes of critics
- Tanya Tucker and Lucinda Williams
- Writing a hit song