I bootstrapped a company in Pittsburgh in 2000 (the founders all came from CMU - I am from France originally) with a good exit in 2012. When I moved there the food scene was nonexistent and people in the US still perceived Pittsburgh as a bad place to be (e.g., a lady I met in CA responded with "Oh I am so sorry" when I told her I was living in Pittsburgh). CMU also didn't really understand startups - we were the fir…
Why do you need access to so much money that you can't get it in Pittsburgh or remotely? Seems like an insanely cheap place to bootstrap. Get to break even far faster, etc... If you're living in Manhattan now, you could reduce costs by over 75% by moving back and put it into the next venture instead. Plus, the kids get the dog and a yard.
But if I had to do it again, especially in the current VC environment, I would raise money. It can be slow and tedious to bootstrap (took us 12 years to grow to 125 people and exit) and a lot of good startups in Pittsburgh seem eternally stuck in the seed stage.