Ricky Montgomery

April 3, 2026·47 min·3 clips

Ricky Montgomery argues the albums you end up loving are the ones you hated on first listen.

The opening takes its time. Joe Pug begins inside The Working Songwriter frame, with writers avoiding the page by talking about the work. Then the housekeeping rolls in. Banzoogle gets the sponsor slot, including Joe's memory of paying a web developer named Remy with an Isuzu Pathfinder. Once the conversation sharpens, it turns toward influence. Ricky talks about a teacher who could walk into class and rip on drums, clarinet, or whatever instrument was nearby. That kind of authority stayed with him. He ties it to an underdog feeling, the chip on the shoulder self-made musicians often carry into the work. Joe catches the shape of that and answers with his own memory of a guitar teacher who could play along to whatever a younger Joe was listening to. The tone stays close, almost like the couch is still in the room. From there, Joe moves toward Ricky's unusual comfort with changing mediums, especially the early audience he found on Vine. Ricky handles the research with some shrug in it. He admits he is trying to stay focused, which keeps the exchange human instead of turning it into a polished career recap. The craft question is bigger than platforms. Joe is asking how Ricky learns the grammar of a new medium and starts speaking through it without losing himself. Ricky's answer starts there. Even in the short excerpt, the pull is less about strategy than temperament, attention, and the itch to prove something. The ending comes back to the song. Joe thanks Ricky for the way his mind works, points listeners toward the album Ricky, and closes with the show's plain reminder to keep the song at the center.

As heard by us

A clear conversation about how songs, discipline, and platforms shape an artist's path.

Ricky Montgomery's turn on The Working Songwriter is at its best when it stays with the small, telling details of how a career gets shaped. Joe Pug gives him room to talk about a strict teacher who could rip on several instruments and the underdog mindset that carried over into…

Read the full review in PlayNext →

Why you'd press play

If you want a songwriter talking through how he found a voice across different mediums, start here.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from The Working Songwriter