How To Collect Money From People Who Owe You

Odd how it works — people who owe you money tend to let it slip their mind, but when you owe them, they remember and remind you of it until you finally pay up.

Since you’re financially responsible enough to read this fine site, you surely are the type who makes good on your debts. But not all people are as awesome as we are, and a subset of these unfortunates happens to be the sort who are happy to go on owing people indefinitely, forcing you to figure out a way to get it back from them.

There’s a fine art to fund collection, requiring just the right touch and sense of timing depending on the situation.

Contractors and other work-for-hire types know all too well the feeling of clients who demand your work in a timely manner but don’t reciprocate by paying up quickly. Although being stiffed may feel like a personal insult (cause it is), it’s best to keep feelings out of the matter and stay detached and professional.

Resubmit your invoice every week until it becomes clear that you’re being blatantly ignored. At that point, send them one last request labeled “final invoice” with a note that says you’ll take them to small claims court for the amount you owe unless you hear back within 10 days.

With any luck, you’ll have to follow through with that threat and wind up on a daytime TV judge show.

My favorite trick is to invite the friend to dinner, strategically ordering just enough food to cover the debt, then casually mention when the check comes that, by some crazy coincidence, your portion matches what he owes you for that thing.

If he hems and haws, make it a hard sell by revealing that you’ve forgotten your wallet. You can take this to the next level by actually forgetting your wallet, but he had better bring his unless you want to spend the evening washing dishes.

You can also make a mutual friend, who happens to hold some leverage on the borrower, into a loan shark and sell the deadbeat buddy’s debt to him at a discount. This works particularly well in roommate situations. If the pal owes you $20 that you know he’ll never pay back, have his bills-handling roomie pay you $10 or $15 for the $20 balance, which he’ll tack on to the amount the debt-forgetful amigo owes him for the cable bill.

Everyone warned you not to float the cash for a car down payment to cousin Hank, and they’re all laughing at you because he spent it all on booze just like they said he would.

Maybe he’ll never give it all back to you, but maybe you can work out a payment plan with him, shaking him down for a few bucks at every family function you see him at. Failing that, coax him to work off the debt by doing odd jobs for you or humiliating himself for your amusement. For instance, you can offer to shave $50 off the debt if he shows up at your kid’s birthday party in a Barney costume.

Decorum and sensitivity go out the window when you’re dealing with the man. Be loud (meaning firm; don’t yell) and visible (making your calls and emails frequent), and get into the ear of decision makers.

If you struggle to get customer service reps to get you a refund, take to social media or launch an Executive Email Carpet Bomb to get the attention of the powers that be. Always be prepared with receipts and correspondence that serves as evidence of what you’re owed.

Don’t be shy about posting your complaint to the Better Business Bureau, which is the equivalent of an aid at elementary school recess who gets bullies to stop beating up on you.

If the amount you’re owed is piddling, and serves the purpose of keeping the doofus out of your life for fear you’ll ask for it, just let the debt hang over his head indefinitely and consider it the price you pay not to have to deal with that person.