What it's like to bootstrap a business before it can financially support you
Oh man.  I bootstrapped a business on the side, and quit my dajob when it got to the point where it could support me (which is to say, could pay me like 1/4 of my market value in silicon valley)   -One of the clearest mistakes I made that could have made the company opportunity cost profitable had I not screwed it up was that I was conserving capital while I had the opportunity to grow really fast.   For a short period of time, because of a blog post someone else wrote, I had a huge waiting list.   I was building servers one at a time, using the money from the first to pay for the next one.    A lot of that waiting list dried up while they were waiting for me;  There is a reasonable chance I would have been 5x bigger at that point had I maxed out my credit and bought servers all at once.   And if I was wrong?  if I maxed out my credit and went bankrupt?  I'd still be better off than I was in reality.10 years at 1/4 salary is... brutal in a way that bankruptcy isn't.  (I think.  I've never actually gone bankrupt.)I guess my real point here is that you need to time box it.   At some point, you need to give up.   I've never worked with VC, but I would assume that it would act as something of a forcing function here.   I think being disciplined about "always take a better job if you are offered one"  might also work.