"With a funky web app, at least your friends and family might understand it and think it's cool."
Perhaps if you're in college, or keeping up your day job. But none of my friends or family thought it was "cool" when I quit my day job after we got a little bit of traction. They thought it was something more along the lines of "completely batshit insane". As I recall, it actually made my parents cry.
The point is: it's pretty hard no matter what you're working on. Everything becomes boring after a while, and outside of the valley it's hard to find a culture where people will actually support a decision to quit your day job and work on a startup.
I look at it this way: you can afford to do something which is just a lot of fun but not making any or lots of money, as long as you are not in debt from other people. The debt can be in the form of money (borrowing from friends or family, investors) or time (ignoring friends and family).
Perhaps if you're in college, or keeping up your day job. But none of my friends or family thought it was "cool" when I quit my day job after we got a little bit of traction. They thought it was something more along the lines of "completely batshit insane". As I recall, it actually made my parents cry.
The point is: it's pretty hard no matter what you're working on. Everything becomes boring after a while, and outside of the valley it's hard to find a culture where people will actually support a decision to quit your day job and work on a startup.