First $1,000 (and first $100, since it was a $1k contract): I made multiple semi-popular icon sets for KDE over 1999-2000, posting them all as FOSS-licensed artwork on kde-look.org. About a year into that I got an email from a random small startup, praising my work and offering me a fixed rate contract to do a novel icon set for their product, a GUI-ified backup client for Linux desktops.
Amazingly, they persisted even after learning that I was 14 at the time. My poor parents had zero idea what it was their kid did on his computer all the time; I imagine the conversation where I passed the phone to my mom to talk to their CTO was probably one of the more surreal things ever to happen — to either of them!
Haha, I was on the other end of this call around 2004-2005. Someone had a nice portfolio of iconography, UX constructs, etc., and I reached out to commission a theme for our software.
She had to ask her parents for permission because it turned out she was 15. I had to talk to her mom and convince her that we were an actual company trying to hire their daughter.
We used that theme for the life of the product, though!
Amazingly, they persisted even after learning that I was 14 at the time. My poor parents had zero idea what it was their kid did on his computer all the time; I imagine the conversation where I passed the phone to my mom to talk to their CTO was probably one of the more surreal things ever to happen — to either of them!