Oakley began making videos in 2007; his first video Raindrops had received almost 500,000 views on YouTube as of November 19, 2017. Since uploading his first video in 2007 while a freshman at Michigan State University, his channel has over 673 million views, and, at his peak, over 7. 5 million subscribers. Oakley, who is openly gay, is a former member of the successful collaboration channel "5AwesomeGays," where he produced the Friday video for over three years. He was featured in the 2014 Frontline investigative report "Generation Like," a follow-up on how teenagers are "directly interacting with pop culture" to the 2001 report, "The Merchants of Cool. " SocialBlade, a website that rates YouTube and Instagram accounts, ranks his YouTube channel, as of November 19, 2017, with a grade "B", subscriber rank of 224th, video view rank at 2,010th, and a SocialBlade rating of 33,897th. As of September 2018[update] he also had more than 6. 2 million followers on Twitter and 6. 1 million on Instagram.