Caniff launched a YouTube channel in September 2012. He posted six second clips of pranks, comedy sketches and videos about his life on Vine in 2013. He later joined the Magcon (Meet and Greet Convention) touring group with Nash Grier, Cameron Dallas, Matthew Espinosa, Shawn Mendes, Aaron Carpenter, Carter Reynolds, and Jack & Jack. In 2013-2014 the group toured the United States holding conventions where fans could meet and interact with the internet celebrities. The original Magcon group broke up after the tour ended in 2014. Caniff then traveled the United States with the DigiTour. In 2015 he embarked on his first solo tour, the RV Project Tour. In 2016 he went on parts of a world tour with a re-boot of Magcon, which included Aaron Carpenter, Cameron Dallas, Dylan Dauzat, Jacob Sartorius and other internet celebrities. That same year, Caniff co-starred in the Netflix reality series Chasing Cameron about the tour. He's done several tours throughout 2017.