1999, created a Magic: the Gathering fansite on Geocities. Pretty sure I made a solid $13 or so with display ads, and would one day go on to make many dozens of dollars with my next Age of Empires II strategy fan site.<p>Good times.
I made tee shirts on RedBubble when I was 14 or 15. Really low quality designs from a non-artist for niche communities. One really caught on. Another two or so got a bit of traction. The other 30 never sold. Ended up making probably around $1,000 total in the end which is great for a kid who can't legally get a traditional job yet.<p>The market is super saturated now, and there are a lot of people with actual talent now too, which is a big win for the market as a whole so I'm glad!
A friend of mine introduced me to affiliate marketing and SEO in 2012. After learning the ropes I challenged him on who could make the first dollar with a brand new site. I made a site about Bluetooth speakers, made my first affiliate sale a month later and won the challenge :-D<p>My affiliate career wasn't very long lasting though. Right now I am trying to make my internet dollars with SaaS instead.
I used to make planner templates and similar things of that sort for myself in high school. It wasn't anything special but I enjoyed making them.<p>I had this guy contact me on Reddit about whether I could customize a daily planner for his kids and gave me a general idea of what he wanted. I delivered the design and he loved it, and commissioned three more.<p>I charged him $2 USD per planner (didn't know how to price it + it took me an hour tops, but he insisted on paying more which was nice). Ended up earning $15/planner.
Most of my internet dollars in the past have come from ads and affilates on various blogs I run.<p>My first real "somebody paying me for my product" dollar, came in January of this year. I launched IndexGuru - solves a super common issue I had been dealing with on my blogs. Posted it to show HN, and had two separate people sign up and pay me money :)<p>Pretty great a-ha moment. Business is doing well, but nothing to write home about, I unfortunately do not have yacht money yet.
Nothing to be proud of, but I once won $50 through betting on ice hockey. I had no clue what I was doing, I just picked a team and put bet for draw every time that team was playing, doubling previous bet. Once I won I took the money and never came back :)