#9. Family to support
PG is wrong when he says "You'll never found the next Google this way", though. IBM was founded by someone who had a wife and kid to support, and had just been convicted of antitrust violations, fired, and had a 1-year jail sentence hanging over his head (later reversed on appeal).
You do need to be hungrier for profits and less willing to trade growth for money. The strategy I'm using (try lots of stuff until I build something useful, then try to get lots of users, then figure out how to monetize it) won't work for someone with a family to support. But the strategy my boss is using (go to your industry contacts, talk to them about their problems, get them to pay you up-front for development while you solve them, reinvest the profits for growth) could work very well.
Seriously, would you consider business with anyone who worked like that? Stumbling around blindly for an idea, followed by hoping that you'll generate a set of expenses, and then finally hoping that you'll be able to earn revenues.
I worry more about you than the bloke with the family to support.
It's often difficult or impossible to figure out what consumers want, other than putting lots of ideas in front of them. Usually if you ask them, their responses will be wildly different from what they actually do. (I maintained that Reddit was a failure long after I started using it on a regular basis, and did the same with LiveJournal.)
It's not a business model that works in every field - in particular, you absolutely don't want to try enterprise applications this way (really, nobody will buy from you if you try it, as you remark). But it does work.
But I disagree that you the best approach is to throw things at the wall until you see if something sticks.
1. Build a basic version of something you think people want.
2. Try it.
3. If people don't like it, modify and try again. Do that for a few times, and if it still doesn't work. Go back to step 1.
Just saying, there's such a big difference between "had been convicted of antitrust violations" and "leaving 9-to-5 cubicle land" that the wife and kid are practically irrelevant to the comparison.
That means you have a year to either:
1) quit the startup and get a job.
2) get some VC funding or enough revenue to live on.
Plus, big company boring jobs are always there for the taking...