He needs to stop pretending like he's some big shot executive with all this money. He should be focused on getting a job using his degree. If he had invested those 4-5 years in getting a job, he wouldn't be in the situation now. He would be earning a VERY decent wage using his Computer Science degree and he wouldn't be broke.
"He doesn't want to work for others." Well no one wants to be told what to do in life. But that's all a part of the business world. Just because he can work for someone now doesn't mean he'll be working for someone later in life.
You always start at the bottom, but you can work your way up.
You don't need a "professional." Just common sense.