This is usually good for a laugh and a story to go along with most of it.
I've always been the entrepreneurial type, so in highschool:
worked with my dad at his cafeteria. Everything from janitor, short order chef, cashier, manager and in house bookkeeper.
I also supplemented my income selling porn to other highschool students. I'd record crap off satellite and I had 3 VCRs setup to record off my master. I'd dub together 8 hour tapes and sell them for $20 a pop. I made some great money doing that.
Lets see, college: I was a bookkeeper and expanding my business. I was also a student consultatant (basically tech support guy for the school computers). I took initiative and pretty much ran the business school network.
During the summer I was a job coach for visually impaired kids.
Somewhere along the line, I started selling porn off and on.
After college, I worked with a CPA firm for a few years prepareing tax returns early in the morning (3A-9A usually) and I also got a brick and mortar storefront for the bookkeeping/tax prep biz. I also opened my hosting company, started a few adult websites and my image hosting websites (paintedover.com and fapomatic.com). Again, every so often I sell porn vids.
These days most of my attention is in the tax prep, remaining bookkeeping clients, web hosting and my image hosting. Of course a little vinyl cutting here and there, but that's really more a hobby than a business right now.
If I had to go work for someone else, I don't think I'd make a very good employee. I'm used to dictating how things work and I'm pretty good at it. Usually when I have been an employee, I end up taking on managerial roles because I have a specific way I expect things to be done.