Nick never wanted to work at all. When he got out of college, he worked at a bank and a financial company for maybe three or four years total. He never had the income from those jobs to support five children and a stay at home wife. Family money seems to have supported him and put him into big houses from the start.
He hated working at the bank. He didn't like having to show up for work or do work. He invented all kinds of medical conditions to avoid work and didn't get along with his bosses.
My theory is that his parents encouraged him to go to law school in his 30s to try and get him doing something by which he could support himself financially and which he would enjoy personally.
So they got him into law school with a poor academic background, paid for his law school & entirely supported his family while he was in law school and then set him up with a law office (with assistant) when he graduated. The lawyers in town welcomed him into the legal community and the lawyer currently representing Montagraph against him offered to help him when he moved into town.
Nick did the law for three years, but then figured out ways to stay home and drink. Then his youtube career gave him the opportunity to shut down his law firm entirely so he could just stay in the house drinking full time.
In some sense, everything that has happened to Nick recently was the inevitable outcome of him being a lazy, stupid, uneducated prick with a trust fund who always thought of himself above working. He is like an adult baby. He has likely never supported himself or his family.
