His first upload dates back to October 22, 2013. From the period of late 2013 to about August of 2014, he would begin to shift his channel from frequent, short Garry's Mod videos with friends to long waited, heavily edited single player videos with more of a storyline. With a smaller base of 7,000 subscribers at the time, he began livestreaming on Twitch, only to take a long hiatus due to work on the channel.
Around this point, he had to start thinking about what he was going to do education wise, as his high school education was done. Originally wanting to go to college for video editing with a side focus on business, he later came to announce on March 31, 2015 that he would be taking a gap year to focus on YouTube full time. As of 2019, there has been no update on this matter.
Around 2016, Tomato would end up meeting and becoming friends with BedBananas. At this point on his channel, he would rarely go back to play multiplayer games with Bed, along with other friends from both older videos and newer ones. As time went on, older friends moved on from the platform or out of the friend group, leading to more of a reason for Tomato to continue doing single player videos. Eventually, he would become friends with Criken2, who along with Bed and Tomato, would create the Rooster Teeth affiliated group known as Sideshow in May of 2018.
Since Sideshow's creation, Tomato has been known to play many games with the group on Criken's Twitch channel. The group, along with close affiliate and friend Shayne Hawke, held their first official panel as a group at RTX 2018. There, Tomato admits before showing a draft of an upcoming video that he feels as tough his channel is "cursed", as every time he goes to upload or render a video, something comes up and keeps him from doing so.
In late 2018, Tomato and Criken were sponsored to face off against each other in Magic: The Gathering Arena blindfolded, as response to one of the earlier streams as Tomato coached a blindfolded Criken (Criken's side of the stream is archived here). In order to show proof that he was blindfolded, Tomato created a throwaway Twitch and streamed for the first time in years. Since then, he has been streaming on his own channel as well as still playing with everyone else when given the chance.
- Tomato owns a cat as seen briefly in a Reign of Kings video.
- Tomato made collaboration videos with Criken2, BedBananas, SleepinGamer, Belowtheshoe, TheMadMax000, MessYourself, VaatiVidya, and MattShea.
- Tomato use to bully SleepinGamer, but in a joking way in any video that Sleepin appeared in.
- Tomato barely knows Jerma985, Although he did go to a arcade with him and Vinny. 
- Tomato is semi colorblind, he has trouble telling blue and purple apart. Due to this he has repeatedly told that purple colors are yellow as a joke.
- Tomato has no feeling in his left foot due to having liquid nitrogen poured on him as a kid. 
- While at a bar during PAX East 2018, a beligerant bar patron spilled a drink on Tomato. Witnesses claim that Tomato lifted the man 12 feet into the air by his shirt collar to meet him at eye level, and aged him 80 years with his piercing gaze before suplexing him into a pile of dust.
- In the Deal With It (Metro: Last Knight) video there is a section of the video of Tomato speaking German.
- On a stream on 12/1/2019 Tomato screamed at his audience during stream to add toilet lore to his wiki.
- The bathroom in Signal Simulator is fake. The toilet paper is made of plastic, the toilet lid cannot be opened and the only source of water within thousands of miles is his streamer bath water. This renders him incapable of wiping or washing his hands after going to the bathroom.
- Tomato cannot whistle.
- Tomato is a huge fan of the Half-Life series stating that he played it as a child in one of his videos.