Why would you want to cash out out of something you love?
These kind of businesses struggle.
But when you have a rich parents, they you come up with some start up idea, hire a team of people to make it - then yes cashing out is a win. But those people don't look at it as business, as a real thing that adds value for other people, but pure selfishly as showing themselves they can pull this off.
These people also often steal ideas from people who care and love what they do. Often those people become wage slaves in those rich daddy companies.
Then don't cash out. But that's usually a fantasy. Nobody is really "passionate about enterprise saas" or whatever the marketing says.
Founders are interested in control and eventual (financial) freedom, and tend to like building an organization in general. An acquisition provides that freedom while allowing them to build something else in the future with even better circumstances.
Was he? Or was it the opportunity to create a business around new tech and the eventual riches it brought? It seems his real passion is buying islands and racing boats.
Because you might love security for your family’s future more than your work. A bird in the hand is worth two in the bush. You can always start another company.
