I mean, when Bill Gates was in High School computers weren't really in general use, so they probably were still doing it on paper. Why say no? They wouldn't have to use it if he failed. Also, did he build it first, or ask for the business first?
Whereas it sounds like this person asked his school if they would convert to his scheduling tool before he had built it to try out? I can imagine a school administrator saying "we'll probably stick with our enterprise contract, thanks" in the 2010s, and it would be a reasonable answer.
I wouldn't personally recommend that one experience be the basis for your East Coast / West Coast judgments.