We actually had some winners in the 90s but many of them either lost their winnings in the dot bomb or never invested in other companies. A few of those winners are guiding their second or third start-ups, too.
Definitely. The main reason they didn't reinvest was timing -- everyone was burnt out on startups even if they had won after the dot.com burst.
But now, FB or Google employees are like, wow, that was awesome, let's do it again. I think the startup scene is more mature now and that reinvestment is more likely to happen outside of SV now -- the key difference is that startups are more stable, wiser, far leaner, and more `cool' now, so it's seen as an actually "safe" bet to re-invest. I know if I ever had a win that's exactly what I would do, in fact being able to re-invest is a lot of my motivation for being a founder.
But now, FB or Google employees are like, wow, that was awesome, let's do it again. I think the startup scene is more mature now and that reinvestment is more likely to happen outside of SV now -- the key difference is that startups are more stable, wiser, far leaner, and more `cool' now, so it's seen as an actually "safe" bet to re-invest. I know if I ever had a win that's exactly what I would do, in fact being able to re-invest is a lot of my motivation for being a founder.