Reading stuff like this is so surreal because it nearly mirrors my own experience starting out. I got my first job through a local linux users group mailing list (CEO took a chance on me to do sysadmin and scripting work) - my mom had to drive me to work after school and pick me up in the middle of the night after I was done.
Now I run a business and when I look back, it's astonishing how large a chance it really is to hire a kid who can't even drive to write software for your business. The 1990s truly were crazy.