Caylen was born in Houston, Texas. He and his family moved to San Antonio, Texas, where he grew up. He has three siblings; Jaylyn, Ava Grace and Joe Felix. His parents divorced when he was very young. Caylen attended high school at Sandra Day O'Connor High School in Helotes, Texas. He briefly attended The University of Texas at San Antonio before dropping out to focus on his YouTube career.
Caylen began his career on YouTube, uploading his first public video to his channel, Life with Jc, in 2010. Caylen also gained exposure due to the YouTube supergroup Our2ndLife where he, Connor Franta, Ricky Dillon, Kian Lawley, Trevi Moran and Sam Pottorff went on an international tour and amassed a total 2.7 million subscribers before the group broke up in December 2014.
In 2015, Caylen's compilation album Neptones hit number one on the Top Dance/rap Albums chart, according to Billboard Magazine, the album was from Heard Well, a record label started by YouTube user Connor Franta, CAA new Agent Andrew Graham and entrepreneur Jeremy Wineberg.

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