There is no place (other than the bedroom) where begging should be involved. If this outfit hasn’t paid their outstanding, legitimate invoices, follow some standard accounts receivable procedures. First, send a demand listing what the outstanding invoices are and their dates. Tell the debtor that he has 15 days to settle these accounts or you will taking further legal action. If the deadline expires, consult with an experienced transportation paralegal and begin the collection process. It is only $2500, so using a lawyer might be cost prohibitive, unless he is your brother in law. Often times, just receiving a Small Claims Court order is enough to get the deadbeat off of their wallet. Be prepared however, if the debtor decides to play hardball, you may have to accept a $2500 lesson in who you are extending credit to.