The total amount you are owed dictates which court has jurisdiction. For example, in Florida the statutory limit for small claims cases is $5000. When you sue for an amount above $5000. the proper jurisdiction is County or Circuit court. If you were owed $1000. a month for the past two years you must be owed more than $24,000.
To initiate a court case to collect a debt the first step is to file a Complaint and Summons and have the other party served by civil process. You don't say where the other party is located. If the other party is in another country or state, your case becomes more difficult.
Florida Statute 559 governs debt collection practices; and there are federal laws that must also be followed. An attorney or a collection agency may be your best avenue in collecting your money.