“Winning Feeling” started out as a submission to a contest to create a song for a lottery. It did not make the cut, but B.Reith still loved the song. Though he does not want to promote gambling, he says that in life “If we don’t try, if we don’t give this a shot, we can’t win.” He wants to encourage people to not let the failures of their past determine the success of their future.

When finalizing the tracklist to Heart On My Sleeve, B.Reith wanted to include this song. He thought that Christon Gray would make a great addition to the song, and Gray obliged. “I think that song translates very well to taking that leap and going after a dream or a goal.”

In the years after B.Reith moved to Nashville, he was signed to a record label and had a team of people to support his career. Despite how wonderful that time was, he says that he came to a place when “the specific wiring of who I am as an artist doesn’t totally fit into what we would call the Christian Music industry.” He believes that at this time he fits better as being an independent artist. This is what inspired his song “Start Over.” He says

“Failing, maybe that’s not what I should be afraid of. Maybe that’s not the worst thing. Maybe not trying is the worst thing. Maybe my fear of failure is the problem that’s keeping me from doing anything.”

B.Reith wants listeners to know that they can always get up again and move forward.