Why can the boss judge your worthlessness based on just one conversation?

At a dinner gathering, there was an investment big shot and a young guy.
The project the big shot invested in has a very low failure rate. Everyone in the circle says he's sharp-eyed and has a keen eye for people.
The other young man was brought in by his friend, a graduate of a prestigious university, with an impressive resume, and has reached middle management at a large company.