Not to out just how old I am, but I kind of did this in high school. I was one of the only people in my grade that could type well (about 60 wpm, nothing crazy), so I would type everyone’s handwritten essays for quick cash. It did not net me six figures, but maybe that’s because I went to high school with a bunch of farmers and paper mill workers’ children and not wherever Cuban sends his kids.
I was way too much of a goodie goodie to ever do that, but I definitely should have.
For lunch, my family qualified for free lunch. The way they distributed this was once a quarter we would get a collection of tickets to last that whole period. I’d tear one off every morning to take in to school. One year, there was a quarter where I didn’t get get my tickets. So, I had to go to the school office once a week that week and get another set of tickets and the office ladies always assumed I was full of shit, but they gave me the tickets.
When the snow melted, we found a bunch of mail in a snow bank. Guessing a plow or something knocked them out of our mailbox and buried them all in one go. My parents had me do the honest thing and take the tickets to the office to surrender them, but the ladies were so impressed I was actually telling the truth the whole time, they just laughed and let me have them. I sold those to other kids, mostly other football players that wanted seconds, and lived like a king during that period (was able to buy a few Magic: The Gathering boosters).