For web startups, what is the advantage of living in a startup hub vs living in a city like Philly or Orlando?
It seems like being in a startup hub matters most when your company grows to a certain size and you either need to hire a lot of people or need to raise money. How much does it matter for a company with 1 - 5 people who aren't looking to raise capital and aren't trying to become the next Facebook or Twitter?
My frustrations with living here:
1) Most events I want to go to are Way The Heck Over There. Going over to Tokyo for an HN meetup takes a total of six hours of train rides and $200. Going to the US for a conference takes, ugh, don't get me started.
2) To the limited extent that my life requires that someone who is not my customer understand what I do for a living, my life is needlessly complicated. My landlord, my bank manager, and the local tax office/city hall think my situation is very "exotic" relative to what they are used to. It is nothing that I haven't been able to finesse, but nuisances are nuisances. Similarly, the selection of lawyers/accountants/etc who are prepared to deal with me is more limited than it would be in e.g. San Francisco (or Tokyo or Chicago, for that matter).
3) There is one programmer in this town I'd consider hiring.
Now, does that matter? Meh, not so much. I launched a multinational telephony company from here this week. We are living in the future. The Internet is the greatest geographical leveler ever, and the situation keeps getting better. APIs keep getting better, enabling you to do more and more sophisticated things with less and less investment. Hosting keeps getting better: in all probability, I'll never own a server, and that is a viable option now. Options for extracting money from paying customers keep getting better. The funding environment is even getting better, although that is slower (not too relevant for me at present, but nice to have options).
There are some compensating advantages:
1) This town is my home.
2) While Japan is not exact a low-price country, a modest apartment in San Francisco costs about what I need to live comfortably here.
3) Being ramen profitable here is delicious.