I have watched a peer leave his well paying job, TC ~500k, to grind it out for 10 years trying to build a startup on what I knew was a completely stupid idea, in the hopes of getting rich. I watched him work 16 hour days, miss vacations, destroy relationships, pivot and ultimately fail. All because some VC threw him and his idiotic cofounder a bone when money was cheap.

I have to wonder if they ever think about how they'd be sitting on >$10m if they just stayed where they were, kept their equity and enjoyed the stability.

Startups are a young man's game for a reason. When you're young you're usually too stupid to realize what you're giving up, but it doesn't matter because you have all the time in the world to start over. Starting all over in your 40's is just depressing.