If your worried about money, is suggest getting a job at a decent company (reading between the lines it sounds like you've put your time in ventures) and having a financial plan. A small dose of austerity and planning can make you a millionaire in a short time, with relatively little risk. It won't be more money than you know what to do with, but you'll be comfortable enough to retire and then be as lazy as you want. Or you'll have the financial security to pursue a venture comfortably.
The great thing about living frugally is you can actually have a great lifestyle while doing it. For example, I could re-create a fancy $10 breakfast sandwich from a local coffee shop in 10 minutes and for less than $1 per sandwich. You can eat like a king for a fraction of what eating out costs, and you'll probably get better quality.
If you're in the bay area, you should probably get out unless you're being paid enough to make it worth it (most aren't).
In ten years you can have far more security, money, and free time than the average person can even think of. And its really not that hard. For a techie, living paycheck to paycheck is very much a choice.