Comment by Arete314159

For the vast majority of people, becoming rich is a means to an end. More time to make art, freedom from stress, ability to travel more, or just the fun of buying lots of toys.

He keeps talking about wanting to do something "important." But I think he is conflating the "prestigious / expected" meaning of important with another interpretation: "meaningful."

Plenty of next steps for a founder are prestigious. But few are meaningful. Most new companies make money by finding efficiencies and disintermediating people from processes in various ways. This usually means pushing an entire sector (like travel agents) out of gainful employment. For whatever reason, Silicon Valley startups rarely punch up - they don't find efficiencies in health insurance or healthcare billing, they don't do "Moneyball" for CEO's and figure out how to run a company for less, they don't find efficiencies that cause us to pay less money to the rich (except Cost Plus Drugs).

No, they punch down, and make increasing numbers of the middle class into the new precariat. For that, the founders are praised and told that they are important. But the work, being morally questionable, is not meaningful.

  By contrast, many meaningful endeavors are about charity - giving access, opportunity, dignity, and money to those on the bottom rungs of society. 

  The emptiness he feels is a lack of meaning, but he's trying to fill it with more prestige, and that's why it's not working.