First ~$50: I ran a web proxy website in high school that allowed students to bypass the web filter installed on the network. This was back before literally ev

First ~$50: I ran a web proxy website in high school that allowed students to bypass the web filter installed on the network. This was back before literally everyone had a cell phone and before 4G, so it was really the only way to surf MySpace, eBaumsWorld, and YouTube during class. I had no idea what I was doing, but somehow I cobbled together this site with PHP so that people could pay for an account through PayPal. I gave away accounts to various students and even a few teachers started using it. Every time the web filter blocked my domain, I just switched to another domain and sent an email to all my users with the new link. I didn't make much revenue because I only charged people a few bucks, and the site might have been a net loss, but it was fun and mostly for my benefit. First $100: In the early days of YouTube, I ran a fan site for a channel and had permission from that YouTuber to collect ad revenue in exchange for running the site and backing up their content. First $1,000: Probably the ad revenue from the same site I was running, but other than that, I got some freelance web developer gigs years later that paid out far more than that.