He'd been writing music and making albums since he was 15, and by the age of 26, he felt like he was spinning his wheels. He knew he needed a change, so he ended his old band Sequoyah Prep School and moved to Cuba. He thought he might be done with music for a while, but the songs just kept coming.
"I had this idea in my mind that I was going to try and join some kind of Latin American Leftist movement. I wanted to jump off a cliff," Osborne says. "Once I got there I immediately started hanging out with musicians and going to shows. I started showing them the songs from this project that was kind of just an idea in my head.
"They were like, 'man, don't throw away your passport, go home and continue to make music,'" he says. "I was encouraged by them to try again."
Osborne ended the relationship he was in, started touring and writing constantly and eventually dropped out of school with just one paper and exam left to finish. He also made an aesthetic upgrade, getting the words "Acid Boys" tattooed across his knuckles.
"I was always afraid of committing fully to the idea of trying to make it. I think in some ways, that's what held my old band back. I thought maybe I'll go to school and I'll be an anthropologist and go live abroad," he says. "Then I did all that, and I realized no, I need to go back to what I'm good at. I got the knuckle tattoos to keep me out of everything else."