Finances
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Tony is unique to most lolcow-esque content creators in that Tony is entirely financially independent and is actually doing quite well for himself, managing to own a house without government support/welfare. He's been able to consistently hold jobs, but recently he got laid off after his trucking company downsized and is not doing very well financially.
Jobs
Tony is a trucker and has been working in trucking, probably since he got out of high school
Before Milton trucking, his employment is mostly unknown. There have been mentions of Snyder trucking, but that's just it.
Recently, in 2023, Tony got laid off from "Milton Trucking." If you look for Milton Trucking on google maps or for a website for Milton Trucking, you will soon discover that "Milton Trucking" does not exist outside of PA and Ohio. This could be due to Milton Trucking closing down, hence the layoff.
Employability
Tony probably passed high school and has no college education, so right off the bat his employability is somewhat limited. He's also mentally ill and unstable, so his ability to get an maintain a job, especially customer service ones, are also very limited by that.
Tony has also lost his CDL license after a "satellite attack" on the steering of the truck he was driving a test to renew his CDL license, so his future in trucking is debatable. He also failed the written test for a forklift certification due to him slamming on the keyboard for some reason, so getting work in a warehouse would be difficult.