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Asking to pay less is almost always a wearying and unwelcome question...with one very special exception.

The Magical Six-Word Question That’s Saved Me $1,140 in Three Months

I’m a little wary of asking for discounts, especially from very small companies. When it’s just one or two people running the show, it means those one or two people spend an inordinate percentage of their time doing things they don’t like to do. Nobody starts their own business because they love filing quarterly taxes—they soldier through it for the 10% of the time where they’re actually doing the thing they love.

And every small business owner I’ve known has lost sleep over their pricing. No matter what you’re selling, there’s local and global competition for it, and consumers have tools now that didn’t exist 10 or 20 years ago that allow them to find, compare, rate, and review similar services. The world is a buyer’s market, and it’s really hard to measure what you know your work is worth against what you know people are willing to pay for it. Asking to pay less for the same product is almost always a wearying and unwelcome question… with one very special exception.

There is exactly ONE magical six-word question a consumer can whip out that will make my small business owner’s ears perk up.

“Do y’all offer a cash discount?”

I am...interested.

The cash discount

Ah, the cash discount. Holy grail of the sole proprietorship.

Now, there’s obviously nothing illegal about paying for goods and services in cash—and a cash discount is common in many venues to save the company from a card processing fee. But when a truly small business person accepts a cash payment, it is now on their own conscience to report those earnings to the IRS. I’ll tell you right now that it’s a hard world out there for small businesses, and the option to use an off-the-books cash payment to quietly buy four months worth of groceries is a temptation not many will resist. In any case, what the business owner does with their money is not the consumer’s responsibility. The important thing is that most are eager to lower their prices in exchange for a wad of bills.

So how do you go about asking? This technique works best on non-chain, mid-ticket purchases that have some service component attached. Goods often have a fixed cost, but service charges are set at the owner’s discretion. (That’s why this trick won’t work on a chain that sends service people to you, say Stanley Steemer; it also won’t work in a place like a restaurant, where the cost of the goods and overhead drives the prices on the menu. But a special shout-out to anyone planning a wedding: I guarantee the cash discount will become your best friend throughout this process. Everyone from invitation designers to cake decorators to videographers will be tripping over themselves to give you a healthy discount for cash.)

Getting it right

Talk to your service person first and get a somewhat firm commitment from them on the price—then drop your magical question. If you bring it up too early, a savvy individual may bump up their quoted rate to compensate.

I’ve asked this question twice this year, and met with success both times: our tree removal guy gave us a discount of 20%, or $690. My car repairman gave me a 10% discount of $450 on a major collision repair. That’s an extra $1,140 in my pocket thus far in 2016, with a whole ‘nother nine months to go.

It should go without saying, but “cash” means “cash.” When you go to the bank and request a few thousand dollars from your account, your teller will likely advise to you to go with a cashier’s check or other workaround. But your service person will be expecting a sketchy envelope filled with dead presidents. Do not disappoint them. Just be careful about withdrawing too much—$10,000 is the amount at which the bank begins reporting the withdrawal, and avoiding the reporting with multiple just-under transactions is illegal. (I am not a lawyer so much as a television watcher, so keep that in mind, please.) You don’t want to invite scrutiny with multiple just-under-the-limit withdrawals. You’re not doing anything wrong, and you have nothing to hide, but nobody likes unnecessary scrutiny.

Finally, the “y’all” is very important for the tone it sets. You may substitute the regional dialect you’re most comfortable with, but always be friendly and chill with your service person. They are far more likely to give good service and good prices to someone who is sane, reasonable, friendly, and pays on time. If you have someone coming to your house to do work, small things like offering them a glass of water and making it clear they’re welcome to use your bathroom facilities can go a long way. For off-site services, use lots of “pleases” and “thank yous” and don’t be afraid to throw a “sir” in there too. (Don’t reach for a female gender equivalent, for there be dragons.) Learn their name and use it often.

The more people like you, the more likely they are to help you out. Even if you don’t leave with a discount, you’re making the world a slightly less crappy place by being present to service people, who get their fair share of rude jerks shitting on them.

The more people like you, the more likely they are to help you out.

Obviously being able to pay for expensive services out-of-pocket is a sign that your life has been hashtag blessed. Don’t feel like you’ve failed if you have to put an unexpected expense onto a credit card, that’s why the good lord gave them to us. Aim for cash payments when they are within your reach, and your multiplying fortune will soon be ready for more.

3 thoughts to “The Magical Six-Word Question That’s Saved Me $1,140 in Three Months”


    I’m so stealing this (will give credit where credit is due – though I don’t like living on credit – but I will still mention exactly where I got this idea). CHEERS BITCHES – lots of love too.

  2. This is the perfect time for this article. We are contemplating tree removal, but GD is it expensive! Who knew climbing a spindly wooden thing and sawing off the part you’re clinging to would cost a heap o cash… but if I offer a literal heap o cash, maybe they will agree to a slightly smaller heap…

  3. Tax accountant experience: some small businesses like to slip cash payments by the tax man because there is no paper trail. Just be aware if the discount seems too good to be true.

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