What you're missing is that he was able to build his company, run it for years, get paid well and step down from the CEO position with a stake worth a couple of billion dollars.
You can't always reduce everything to money. Lots of entrepreneurs, perhaps the majority, would consider Drew's outcome to be the ideal one: you get to do what you love, raise your baby and earn a fortune.
Not everyone wants to sell out, start a family office and spend their days on a boat pondering what the purpose of life is and what they should do next.