To put it in perspective a bit, I have scraped together $7000 in savings (over the past year) and plan to live about 6-7 months on that once I quit my job next

To put it in perspective a bit, I have scraped together $7000 in savings (over the past year) and plan to live about 6-7 months on that once I quit my job next month. I live in Boston too. I can't even comprehend having 100k in the bank. There are many reasons which make it difficult to quit, but one of them is definitely fear of not feeding yourself. Sit down and honestly evaluate your budget. Unless you have kids and a mortgage (which at 24 I'm guessing you don't), I can almost guarantee your 100k will last you at least a year while still eating like a human being. As an aside, there are many ways to go have a more fulfilling career that don't involve betting everything on a startup. You could do freelance work, or develop micropreneurial apps, or spend some time learning new skills and then finding a more exciting desk job.