[yranadive]

Your risk tolerance should be a function of your confidence in turning your company in to something of future value. It seems like you haven't done your research on your probability of success yet. I'd advise talking to investors about your idea to get a sense of that. Try approaching them to get seed funding. If you can't raise, quit, and try raising again.

If you can't raise within a year, go back to work. You need to talk to investors to get a feel of how people will value your company if you take the plunge. If you feel your probability of breakeven is at least 50%, I'd say go for it. Keep in mind, every person that joins your company after you will do an implicit probability calculation, so think about what makes you unique and hence more likely to succeed.