Startup has decent level of traction. Been finding it hard to attract investors. Exhausted Midwest and Southern options. Live in the middle of the country where investors just don’t have much risk appetite. Should I move and go to SF/NY/insert startup hub with roughly 20K in the bank and see how long we can last?
Pros/cons of doing such a thing?
The major con is the cost of living.
Are you making a profit yet by bootstrapping ?
OP: Not yet.
is it expensive to live on the outskirts of S.F. ?
Yes its expensive. SF Bay Area is called the silicon valley because it sits between two mountain ranges and hence the real estate all over is pricey. Plus folks don't like development here so whatever open land is not available for development.
However you could go over the mountain range into Antioch, Pleasanton etc which is much cheaper but you're no longer in "SF".
Why don't you go on eventbrite and pick a week where there's a bunch of startup events and pay a visit to SF/NYC and talk to some investors and startup companies to get a vibe before making the big commitment to move?
You can also reach out to startup founders/investors through twitter, linkedin or clarity.fm
or Kickstart it ?
Truly depends on your product. Is the reason you don't have profits now because you are trying to sell it to the wrong market? Will insert city have a better market for what you are doing?