Thanks for being so open. I like hearing real world experiences. My take away here is that unless you are founder, or the company goes for billions, you don't really make much.
This. It's really easy to make money in hindsight. If you'd bought GOOG at the IPO in 2004 and held it until 2007 you would have had a 6.6x return. If you'd held it until today you would have had a 13x return, but a much lower IRR. On the other hand, if you'd bought Zynga at the IPO you'd be down 66% five years later and still waiting for it to bounce back.
It's a lot easier to make hypothetical money in the past than it is to make real money in the future.
On one hand, the only reason to work for a start up is to take the risk and go all or nothing. On the other hand, I would never invest in a start up.
I probably would sell off a huge portion (~70%) of equity before the start up reaches $500 million given the chance
We went out for $1B though (on raising < $2M of VC money)
Sadly I was not in that group of people