" The other option is being a remote worker for someplace cool but you usually need to have a career somewhere else for a few years to make connections."
I thought this was true, but a recent job search proved this to be quite wrong (at least for me). There are plenty of telecommuting jobs out there now that do not require previous experience with the company or telecommuting in general. Additionally there are more and more purely distributed companies out there that don't even have an office (a possible solution to you start-up problem). You may not get paid SF/NYC salaries but you can get close enough (especially compared to the average pay for your area).
I thought this was true, but a recent job search proved this to be quite wrong (at least for me). There are plenty of telecommuting jobs out there now that do not require previous experience with the company or telecommuting in general. Additionally there are more and more purely distributed companies out there that don't even have an office (a possible solution to you start-up problem). You may not get paid SF/NYC salaries but you can get close enough (especially compared to the average pay for your area).