I would consider living in the small town if the tech industry (since I want to work in tech) thought that the retail industry was less important, but most people that I asked seems to think the industry does not matter.

Regarding the work, the startup seems more interesting but there are cool things to do in retail as well. I got both of the jobs offering because I worked as a consultant for the startup solving a problem for this retail company, so I really think the work will be similar but the startup will be more diverse (different companies and etc...)