Yearwood was born in Trinidad to Edward Yearwood, a well-known composer and mother Mairoon Ali, a Trinidadian actress, radio personality and teacher. He established himself as a Soca talent early on when he entered and won multiple talent shows while still in his teens, including the national Junior Calypso Monarch competition. His shot to global fame when he won Trinidad's famous Soca Groovy Monarch/International Soca Monarch in 2015, performing his blockbuster single "Ola." He is the very last International Groovy Soca Monarch champion, as the competition's format was changed in 2016 to exclude that category.