[noonespecial]

Although they deliberately choose to remain at the 'loser' level in terms of the org chart, they have a 'sociopathic' level of awareness of how the business operates (maybe from being an early employee or founder of previous startups). They're never truly comfortable at the 'loser' level, but maybe not willing or capable of making a move to the 'sociopath' level...

The Steves, Wozniak and Jobs spring instantly to mind.

Did the Woz have fun during his career. Absolutely. Did Jobs? Well, that depends...