Many jocks finish college while barely being able to read, many students cheat their way through, or barely make it through with low grades. Going to college is much more an indicator of your social values rather than your skills.
Most people tend to go to college because they're expected to, it has a lot to do with the values your parent instill. Many people skip college because it never occurred to them they should go, their families simply didn't instill those values in them.
College is nothing more than a place where one can learn, it does not mean one does learn. People who enjoy learning don't ever stop learning and self learning eventually becomes a requirement for all who want to continue to grow. College is nothing more than a kick start for a minority of society, there are many other paths that are just as successful.
Many of the most successful companies in the world were started by college dropouts who realized school was getting in their way. Classrooms are good for teaching the masses, people who learn faster than average will absolutely feel like they're being held back and turn to self directed learning as the superior method it is.
If he dropped out to execute something (like start a business), then it is a major plus point. If he dropped out to go work in a dead end job, or to become an 'artist' then this is a sign of a person who cannot complete projects.
I mean, why would you drop out of college to go earn $3000 a month when you could just finish college and earn more than that?
I would NEVER discriminate against a person because financially they had trouble going to college. But I would see it as very negative if a person complained about college not being the right thing for them. Learning is learning, there is no right or wrong way. Everyone does it his way.