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JealousGuy was Tim's first Youtube channel. The account was created on April 24, 2006. When he first started, he would talk throughout a 9-minute video, but he didn't know how to cut out parts yet, 'til his sister showed him. He was always frustrated, and even lost sleep, on getting the right take on a certain topic. The oldest JealousGuy video available to watch was uploaded on November 10, 2006, but it is very likely that there used to be older videos on the channel. Tim took down many videos during the trolling fiasco. Today, the channel has nearly one million views, but only 5, 518 subscribers.

In some of his JealousGuy v-logs, Tim seems slightly depressed. Eventually, he started his NintendoCapriSun channel. It was supposed to be a secret channel, but it ended up becoming far more popular than JealousGuy ever was. In some videos, he has said that his fans are the reason that he's still alive.

As well as vlogs, he reviewed episodes of the TV show Lost, which he was a huge fan of at the time. In his final vlog on the channel, he fights a Final Fantasy IV Behemoth with a sword.