Great selections, Joel.
I`m going to go with my "instantaneous" thought when I saw the title for your post - both are from You`ve Got Mail. I`m a sucker for a chick flick. ;)
Anyhow, I really like both Meg Ryan`s (Kathleen Kelly) and Tom Hank`s (Joe Fox) characters in this movie.
I admire Kathleen because she wasn`t willing to just roll over and die. She put up a fight because she believed her customers deserved a level of service that a big book store just couldn`t provide. Now, yes, she did end up closing her doors in the end, but I think that her confidence in herself and her unwillingingness to compromise on her priniciples of service are admirable. Oh, and need I mention that she sought business advice via email...it`s too bad she didn`t have SUN to rely on - maybe the shop would still be open! 
And, of course, Joe`s "it`s not personal, it`s business" attitude is something I admire. I sometimes have to remind myself of this one since I am a pretty empathetic person...
I think if you could combine these two characters` best traits in the proper proportions (which sort of happened at the end, eh?), you`d have the "perfect" entrepreneur.
Fun post, Joel!
Lex Luthor from the New Superman Returns Movie 2006.
Now I know he is Evil. But he was right about the real estate industry. You can`t build new land. Land is a natural resource that you cant make more of.
His nefarious plot to destroy the USA and create his own continent was Evil, yet it taught kids all across the USA that the Real Estate Industry = Power and Money.
I also liked how he tested his Evil plan on a train set model world, before putting his idea into action against the real Metropolis city. He showed the perfect scenario of using case study and product development to test a business...in a purely evil fashion...lol
I also liked how he showed everyone that Gas is the most important resouce because without oil, you can`t fly planes and even if you have an expensive helicoptor it is useless without gas. Lex Luthor proves you can teach kids things in a fun way even if you are an evil movie character.
Number 2, from Austin Powers. While Dr. Evil was frozen and orbiting the Earth in space, Number 2 built Evil Enterprises into a $9 billion/yr business.
Yeah, it was something like Globalcon, and one of their business divisions was a talent agency. That whole scene is hilarious, especially when Dr. Evil says,
"Alright, I`ve been frozen for 20 years, people. Throw me a frickin bone!"