In , Diaz started to gain widespread notoriety from his appearances on The Joe Rogan Experience podcast. He immigrated to the United States with his mother at the age of three, shortly after his father died. While living in Manhattan, he attended Public School ; [ 6 ] after moving to North Bergen, he went to McKinley Elementary School, where he was required to repeat seventh grade, [ 2 ] and then North Bergen High School , [ 5 ] where he won performing arts awards.
His mother died when he was sixteen, Diaz having found her dead in their home. After his graduation from high school, Diaz moved to Colorado. However, his growing homesickness led him to return to New Jersey in ; he initially only intended to spend his twenty-first birthday there, but he ended up staying in the state for nearly eighteen months. He later called this time "the worst eighteen months of my life" and "the biggest mistake of my life", as his cocaine abuse worsened.
He did not enjoy his time there and quit before taking up work selling roofing, which earned him money but failed to make him any happier.
Following his arrest for kidnapping and aggravated robbery, Diaz was sent to prison in , serving sixteen months of a four-year sentence. It took Diaz a further three years to try stand-up professionally despite being often told of his talent; he later called his entry into the line of work "the last resort", as he had had many other jobs since his release from prison.
Before he did his first standup routine, he worked as a doorman at Wit's End. Diaz performed his first routine on June 18, , [ 14 ] at the Comedy Works in Denver, at a show headlined by Matt Woods. In April , prior to his opening spot for Troy Baxley in Boulder, Colorado , Diaz took cocaine before going on stage and had a set that he described as "a disaster". He then ceased to take the substance before a performance.
