Well I didn't start in rags, but was pretty close....so here's the brief version of my climb through various jobs....
age 14 - summer warehouse work
age 16 - summer warehouse work and managing comic book store
This gave me basically enough money to buy lunch at school sometimes, buy comics and videogames, take girls out, etc...nothing more.
age 17 - dropped out of computer science in cegep (quebec's college system wannbe) because I realized it was shit. Started data entry job a friend got me in an ecommerce company.
Moved up to programmer after a few months...then got laid off with half the company when the dot com crash hit.
Started my first work in the realm of porn here, as a designer who got laid off with me started up a small office to run his 10 or so porn sites. Collected unemployment as well as $400/week cash from him, just managing people doing submissions and a designer. Got so hbored started to learn PHP while at work.
Blew all this money partying every single night
age 18 - learnt enough PHP to get hired by IwantU as a junior programmer. Have touched almost every net career possible there, including at one time or another:
junior programmer, senior programmer, sales rep, makerting, systems administrator, project manager, CTO and finally Webmaster.
I've now moved to Costa Rica, have 0 debt in the world, no creditcards, cash to spare and a sweet guarenteed bonus in one more year where my contract is up that I plan to open a bar/venue with.
To top it all off, yesterday I got a 20% raise
