Wizards Realm
The dream of every computer science student in the 1990's looked like this, start a company, work for yourself, and become rich beyond your wildest dreams. Or at least that's what I dreamed of while I was in college. Wizards Realm was my first (and only) sole proprietorship, every company since has either been federally incorporated or a partnership.
I did technical support, built custom computer systems, got into web design and development (before we had anything sane like CSS), did some custom programming (mostly in C/C++), learned about testing and QA, started consulting, tutoring and hax0ring for pay (or dial-up Internet access)... I also had the college contract the company for teaching nights when I took on the role of Instructor for the first time at CDI College in Oshawa Ontario in 1998. Paid personally by day and my company made some cash by evening, win-win.
It was a good batch of experiences for a 20-something year old geek, I'm not sure where I would be today if I hadn't taken this step and started my own company. It opened doors for me, when I took the contract at Rogers Cable in late 2000, I had the company so I could apply for a D&B Number which was required. This wouldn't have been possible if I didn't take the chance. If you've never started a company but wanted too, I suggest that the best time was 20 years ago, and the second best time is now.
I shut the doors to Wizards Realm in 2002 when I opted to take the full time permanent position of Sr. Programmer/Analyst at Rogers Cable and shift away from Freelance/Contract work. This happened to coincide with the arrival of my youngest daughter and a full-time position seemed like a safer bet, in retrospect, it's not, "safe" is a only a sense, it would be about 5 years before I got back to freelance and contract work.