At age 12, Espanto attended Grade 6 at St. Jude Elementary in Calgary, before traveling to the Philippines in 2014 for The Voice Kids. After passing the auditions, he returned to Canada to write his advanced test in St. Cyril School. Afterwards, he returned to the Philippines. Espanto, along with the other The Voice Kids finalists, received a ₱350,000 scholarship from Eton International School. Upon moving to the Philippines, he went to Eton International School and later on took up homeschooling under The Homeschool of Asia Pacific, an affiliate of the Sanston Academy (Texas) where he completed his senior high school with honors. In Grade 11, he was awarded with second honors. In Grade 12, he graduated with first honors and received two special awards, i.e., the Achiever Award and the Excellence in Music and Arts Award.
During the auditions of the inaugural season of ABS-CBN's The Voice Kids that aired on June 1, 2014, Espanto performed Jessie J's "Domino", which he formerly sang during The Next Star at age 11. Coaches Sarah Geronimo and Bamboo Mañalac both pressed their buttons for him, vocalizing that he 'can be groomed to be a recording artist, a total package'. Although Espanto revealed that he was Mañalac's front act during one of his concerts in Canada, he still picked Geronimo stating that she could help him a lot in the music industry.
In 2014, Espanto said that he will not go back to Calgary, Alberta, and that he was staying in the Philippines to try acting and do a project with his coach and mentor, Sarah Geronimo. In August, Espanto became a part of ABS-CBN's training and management center Star Magic. On September 11, Espanto's rendition of Whitney Houston's "One Moment in Time" topped the Philippine charts of Apple's iTunes store, while his rendition of Justin Bieber's "Somebody to Love" placed second. He then staged his first solo concert at the Music Museum; a repeat of the concert was staged on December 19, 2014. On October 25, he made his Carnegie Hall debut as the headliner at the Fourth The Outstanding Filipino Americans in New York Awards, which celebrated Filipino American History Month in New York City. On November 18, his rendition of "O Little Town of Bethlehem" topped the iTunes chart, while his rendition of Jessie J's "Domino" placed second, in which the two were the only local songs to be included on the top 15. And on November 29, Espanto signed a record and management deal with MCA Music Inc. (Philippines). A week after, he and the other three finalists of The Voice Kids (Lyca Gairanod, Juan Karlos Labajo, and Darlene Vibares) held a concert at the Philippine International Convention Center. He also released his first solo album, "Darren", with MCA Music Inc. (Philippines). It debuted at number 1 at the Philippine charts of Apple's iTunes Store upon its release on December 8.