Conner began his stand-up comedy career in 2013, and later attended the Comedy: Writing and Performance program at Humber College, Toronto. After that, he moved onto Vine, where he gained about 350,000 followers. Kurtis did several stand up shows, performing all over Canada. He independently released his debut comedy album “Cuppla Jokes” in 2016, and it reached #1 on the iTunes comedy charts and #6 on Billboard comedy.

The first video on Conner’s main channel was uploaded in 2014; however, the channel began to gain momentum in 2017, when one of his videos gained 600,000 views in two days. Other creators and friends of Conner’s in this group are Danny Gonzalez and Drew Gooden, also formerly of Vine.

Kurtis joined Danny Gonzalez and Drew Gooden during their live comedy shows, the “We Are Two Different People” tour, in 2019.

He is also known for his critique of problematic content on the YouTube platform, and for making fun of others who wish to stigmatise different groups of people. In 2019, Conner and his friend and fellow comedian Jacob Sharpe criticised Sebastian Bails (made famous on TikTok) for mimicking domestic abuse between him and his girlfriend, Lauren Godwin, on their YouTube channel. Conner and Sharpe were both disturbed by the content, frequently commenting in the video that they found it difficult to make light of such a serious subject. Conner later said he would raise funds of $10,000 to the domestic abuse charity loveisrespect, and match it with his own donation (over $16,000 was raised, meaning that Conner made a donation of $26,000 overall). Conner also criticised a ‘female Viagra’ trend on YouTube, which involved YouTubers administering a claimed aphrodisiac for women by spiking their girlfriend’s drink without their consent. Conner’s video was later removed from YouTube as it showed the controversial behaviour; however, at the time, a number of other ‘female Viagra’ videos were still on the platform. He also does more lighthearted videos, and says that his favourite content is film criticism.