Raymond's acting career began when he landed the role of Young Simba in a production of The Lion King at the Princess of Wales Theatre in Toronto. Funnily enough, The Lion King was also the show that inspired him to become an actor in the first place. "My parents had just taken me to see a production of The Lion King on stage in Toronto," he explained to Talk Nerdy With Us in November 2015. "I saw the kid playing Simba on stage and I thought, 'I can do that, nothing special there,' and then two weeks later, I saw auditions in the newspaper and I asked if I could go, and I lucked out and got it."
According to Raymond, his year-long run in the show instilled him with confidence that he's somewhat lost as an adult. As he told Toronto Life in September 2017, "I was never more free and confident than in those auditions and on stage during The Lion King. Today I'm neurotic and anxious about everything."