- Addiction: Gilbert has been open about his struggles with addiction to drugs and alcohol. He began drinking heavily in high school and eventually developed a dependency on prescription drugs. In 2010, he entered a rehabilitation center and has since maintained his sobriety.
- Financial struggles: Gilbert faced financial difficulties early in his career. He worked various odd jobs to support himself and his music, and he even spent time living out of his car. Despite the challenges, Gilbert persisted in his music and eventually found success.
- Health issues: Gilbert has also dealt with several health problems. He was diagnosed with Crohn's disease in 2008, and he has undergone multiple surgeries to manage the condition. In addition, he has also been diagnosed with anxiety and depression.
- Personal setbacks: Gilbert has experienced personal setbacks in his life. He lost his father to a heart attack when he was 16, and he also went through a divorce in 2013. These difficult life events have shaped Gilbert and influenced his music.