<prompt> Human: This might be a little long, and possibly more personal than finance. I guess thats often how it is in these situations though.Im a musician, and have been making my living from playing about ten years now. Im neither rich nor famous and do a lot of gigs such as weddings, parties and whatnot, which a lot of musicians I know would rather teach than do, but I enjoy it.The last ten years I have played with two brothers who have been providing me steady work. Both have become good friends of mine from working together, and one of them is very up front about money, always pays my bill on time and there is no secrecy about the total sum of the gig.The other one not so much. It has frequently been a total pain in the ass to get him to pay his bills, seeing as I send him text upon text about when to expect payment from the last gig. He will at times never pick up the phone or answer me back. The last five years Ive probably had an overdue bill for something between 2-3000 for three years. At a point where I had very little money and he owed me 3000 his brother cashed me out for about 800 to help me out. This I have told him multiple times that he can just pay his brother back from my bill, since I loaned the money from him. This he has said he did, but I know its a lie.There have been multiple friends who have sworn never to work for him again, seeing as he never acknowledges his problem. I know for a fact that he has made some stupid decisions about money, and have always been friendly in trying to get my share. Its now reaching a little boiling point for me, as I have a family and a mortgage and dont have time for his bullshit anymore. I would be ok with him being honest about spending it, but every time he either texts me that he transferred money, didnt I get it and hell check the transfer tonight. I can get this routine for 6 months straight from him.I have been able to secure a few gigs with him and his brother where Ill be the one to bill the total, and this will take care of the remaining 2000 he owes me as well as the 800 heI owe his brother. Seeing as this is a strain on our friendship and the fact that I would like to continue working with him, Im wondering if some of you have any experience with dealing with similar people?Ive been talking to his brother and it turns out that he is owed a lot of money from him. It has come to the point where he refuses to take a gig with him where he wont be able to bill the customer directly. This is a policy I will implement as well.I know that he has been confronted with this from multiple friends who refuse to have anything to do with him. I genuinely care about him and would like to help him, and I wouldnt mind lending him money if there was an agreement I could trust. But I dont think that would solve anything, seeing as he needs to learn to manage his economy.This turned into a long vent without a clear question. What Id love to see is if someone has had similar experiences with people they cared about, and how you dealt with it!EDIT: posted this as well in relationships now  <response>: refuses to take a gig with him where he wont be able to bill the customer directly. This is a policy I will implement as well.There you go. Stop allowing this person to be in charge of your income. 