If you can plan for a year of no net income from your business in a way that's acceptable to your family, and if you can EITHER plan for a 2nd year of modest in

If you can plan for a year of no net income from your business in a way that's acceptable to your family, and if you can EITHER plan for a 2nd year of modest income OR you have good contingency options (freelance work, or in the worst case scenario, giving up the startup to take corporate work), you should be sufficiently comfortable to take the plunge -- IFF you believe in the startup. I generally view the market right now as one where developers will have no trouble finding work if they need it (albeit maybe not the perfect job if you have to do so under pressure). I also view the market as good for startups right now. This is not always the case -- the market will undoubtedly cycle down, at least for startups trying to raise money and generate revenue. If you have 10 customers and you can reasonably project your way to break even & profit, and if the upside of the company is substantial if it grows to a reasonable size, you should do it!