#18 REALLY depends on where you live. If you're in the Valley, definitely. Everyone who is not in a startup there works at somewhere like Adobe and has 10 coworkers who previously founded a Web 2.0 social search engine for pet clothing which promptly flopped. People used to ask me "what do you have to do to become a professional poker player?" and my reply was always "quit your job." It's a lot like that with startups, and everyone within 100 miles of San Jose knows it.
If you live in Ohio, however, "I own a software company" goes a lot further. If only I were single...
I say "I own a company", exactly because "I have an internet startup" seems like an eye-roller. I agree with the previous comment: the fact that we're out-of-the-ordinary in Chicago is one of the things I like best about Chicago.
It's basic salesmanship. Phrase things in the way that sounds best (within the bounds of honesty of course). "I have an internet startup" sounds a lot like "I fell for a get rich quick scheme. Would you like to buy some vitamins?"
If you live in Ohio, however, "I own a software company" goes a lot further. If only I were single...