The only sure fire way to stay alive managing owners and there equipment is to have no leeway; no money - no fly - no exceptions.
Absolutely correct in any "normal" business - but the way Ocean Sky was run was far from "normal". IMHO, one of the main reasons the company went south was simply because the main protagonist had no concept of money. I suspect that at no point in his young life was he ever found wanting for anything, whatever he wanted just "magically" appeared and 'twas ever thus. So giving things away, offering mates rates, making ill conceived purchases and not chasing payments was never an issue because there would always be a large pot of cash in the distance into which he could dip his hand, and the problem would go away. It seems that the proprietor of that pot got fed up with constantly finding someone's hand in the cookie jar.
Let there be no mistake, the failure of this company lies only with one person - yes others there had their faults, but ultimately they were there trying to make the business a success, but the main man was also the main downfall.