Olootu's sophomore music project, Waterside Gentleman, was inspired by his formative years in Bayelsa, where he and his pals would wander to the shore on days when they didn't have class. They would go to the rivers to simply sit and ponder, and one day, very consistently, they ran into a man playing a guitar. They moved closer to him because they both have a passion for music and noticed that he was well-groomed. They greeted him, and he immediately began playing the guitar and telling them tales—mostly about his numerous relationships and the various ladies he had dated. Olootu claims the day was the turning point in his life because it was the day he fell in love with music and storytelling.