Graduated from an Ivy League engineering program in the late nineties. Worked in four different start ups. Never made any money. Of those four startups I only count two as being valid data points as they were funded by "good" VCs. The others were funded by rich people who in retrospect did not know what they were doing. Now on my fifth startup as employee number 15-20 (not sure which since we are growing so fast). We…
Good luck on your 5th startup. I always wonder for people in your situation how long one can stick it out before decamping to somewhere more affordable to start a normal life (house, kids, etc.)
We can't afford to raise teenagers here ... but we do plan to live here until our first kid is 2 (kid not conceived yet ... just planning ahead).