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 onl

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 are funding growth out of VC money. Good name brand VCs that everyone here would be happy to take money from. Still, I have learned my lesson. I make my life plans as though I can only depend on my salary and my wife's salary. Luckily for me, my wife is a lawyer from an Ivy and makes enough money that I don't worry about failing too much. Even though most of my peers who graduated with me are independently wealthy (Yahoo, Google, Twitter, Facebook, etc.), over the years I've learned to moderate my life expectations. My wife and I don't expect to ever afford a big house in Silicon Valley. Our long term plan is to move somewhere cheaper. That is unless startup #5 succeeds in a big way ... HAHAHAHA lets not kid ourselves. But its fun to imagine :)