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)   -<p>One of the clearest mistakes I made that <i>could</i> 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 <i>lot</i> 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 <i>still</i> be better off than I was in reality.<p>10 years at 1/4 salary is... brutal in a way that bankruptcy isn't.  (I think.  I've never actually gone bankrupt.)<p>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.