That credit card thing actually does more damage to him than anything. That sticks out like a sore thumb. It'll take decades to build trust again on that alone. Someone even with a very low paying job could have made just a call, and made an arrangement to pay a little over a grand a month back then (closer to $1,500.00 per month now with the interest rates), and had that paid off in two years.
Anything serious in business or work, with really large amounts of cash or dealing in any of the really valuable goodies like weapons, drugs, radioactive material people will pay an arm and a leg for; and either the people you do business with or the government is going to do a lot more investigating than just a routine criminal, drug, credit, and background check. They won't get very far. That will really stick out as untrustworthy and irresponsible; especially for someone of his background for it to get that far.
Secondly, just the sheer amount of litigation will stick out right away. None of the individuals who make things happen are going to want to be involved with him in any manner. Litigation, unless it is really one-sided in your favor, is something anyone, with anything on the ball, avoids.
He's finished from anything worthwhile until well into middle age, and that is if he turned things around immediately, which he is no signs of. He has put himself into a hole that will take at least two decades, again if he straightened out immediately, to build out of. This "CEO" isn't even as valuable a member of society as a teenager who is clean and doing something, anything, constructive. Jake is his own worst enemy and hasn't figured out even that much yet. Honestly, I don't think the kid could manage to figure out how to put his hand through a wet paper bag.
Red flags are us.
