5 Customer Horror Stories That Can Make You Regret Being an Entrepreneur | by Rachel Greenberg | Aug, 2022

And how to deal with them without throwing in the towel or derailing your entire business.

5 customer horror stories that can make you regret being an entrepreneur. And how to deal with them without throwing in the towel or derailing your entire business.
Photo by Ricardo Díaz on Unsplash

Customers are like bosses, except worse: They don’t need a documented reason or excuse for their behavior, and there is no HR team to police them. That said, if you’re a current, future, or aspiring business owner, mastering the art of catering to, communicating with, and in some cases keeping your cool around difficult (or shall I say “colorful”) customers is going to be crucial to your long-term success.

Why? Because in today’s digital world where news travels fast and bad news faster, mitigating or abating negative customer outcomes and instead cultivating an overwhelmingly positive reputation for your company isn’t just a good idea; it’s required for entrepreneurial survival.

Thus, I’ve dredged up five customer horror stories from my trove — and yes, after dealing with thousands of customers across multiple businesses, you, too, will have a trove. Let these be a cautionary tale as you embark on the most frighteningly unpredictable aspect of business: dealing with people.

If you told me ten years ago one colorful customer would pollute or infect the rest of the happy campers purchasing our products, I would have laughed. There’s no way one outlier could have that much of an impact — so I thought. Today, I know firsthand that those eccentric special situations may rapidly spread toxicity like wildfire throughout your business.

Some of the difficult ones purposefully attempt to sabotage your company, smearing your name with negative comments, damaging threats, and causing enough digital uproar to scare off prospective buyers. Others, however, may unknowingly scare off would-be customers by just being their socially unaware selves, and those are the ones you’ll never see coming.

Not too long ago, one of my companies offered a service catering to multiple business owners at once, which we’ve done hundreds of times. This time, however, was the first in which a problematic client’s inappropriate demeanor seeped into other clients’ experiences, despite his oblivion.

This outlier swiftly scared off and discouraged the less-advanced clients, while also hijacking the joint service and attempting to hoard resources for himself, at the other paying customers’ expense.

The most difficult aspect of catering to a wide array of customers is the need to treat each paying client with the same level of courtesy and service, regardless of their behavior. This wasn’t a low-end or budget-friendly service, so my company had a lot to lose by offending the perpetrator; however, we had far more to lose by failing to guard and protect the rest of the group.

The lesson? Sometimes you have to protect your customers from each other, and if you realize one bad apple is spoiling the whole bunch (unknowingly or not), it may be best to cut them loose.

The first rule of marketing a product or service should be determining exactly what it includes and entails, as well as what it doesn’t. Don’t overpromise, don’t exaggerate, and don’t lead your customers on if you’re not going to follow through. Sounds simple, right? It is — but sometimes they still won’t listen.

Over the years, I’ve experienced my fair share of insatiably hangry customers who simply can’t be pleased, placated, or satisfied, even if you bend over backwards, give them the moon, sun, stars, and some complimentary fries with that.

While the simple solution might be to say “no”, that can get dicey when these hungry customers turn hangry, and their demands morph into threats to badmouth your business if you don’t comply with their growing laundry list of requests (to which they were never entitled). Though I’m not proud of it, I’ve spent as much as four months back-and-forth with these hagglers, who are always asking for more free breadcrumbs and refills, despite having their fill.

At some point, you’ll need to toughen up, stand your ground, and set the boundary around exactly what they’re entitled to and what they aren’t. If you take anything away from this article, you’ll hopefully do so long before wasting four months on the receiving end of their threat-laced pilfering. It may not look like stealing objects from a store, but if they’re clawing items or services of value away from your business without paying their share, it’s thievery just the same.

Ever heard of a love-hate relationship? It may work for some people, but when it comes to customers, you probably don’t want haters, no matter how green their money is. Sometimes, however, they just won’t go away!

I know it sounds ridiculous, but I’ve experienced customers who have made my team’s life a living you-know-what, insulting our products, services, marketing, branding, credentials, and you-name-it. If they insulted, decided not to buy, and went away forever, we’d all brush this off as a wrong-fit customer. The problem is that some of them still insist on purchasing, once they’re through delivering their platter of objections and disparagements.

For example, some of my salespeople have sat through thirty minutes of a prospective client comparing our products to competitors, attempting to poke holes in our backgrounds and credentials, and frankly asserting that we have little business selling whatever products or services we may. Again, that would be fine if they’d take their insults and be gone. Sadly, a couple of memorable ones didn’t.

Pro tip to anyone dealing with a hater and berater who’s hell-bent on buying your product or service: Do whatever it takes to identify them early, then decline, block, or reject their purchase. They’re likely to be far more trouble than they’re worth. What’s even worse is that in my own experience, politely declining their request to purchase your product or service often makes them want it that much more!

So many marketing gurus focus on overcoming objections, implying that a salesperson’s job is to turn every doubt, question, or “no” into a “heck yes” and a sale. Personally, I disagree. While I understanding overcoming objections that may be due to a misunderstanding or misinformation (or missing information) about a product or service, I don’t aim to be in the business of twisting arms, begging for sales, or making promises or assertions my company can’t keep. It’s not worth the money because it likely won’t last, and if it does, the reputational damage to follow will cost far more to repair.

Simply put, if a customer needs ten rounds of convincing, asks 358 questions, and requests hour-long phone calls with the company’s founder, that may be an indication that they aren’t quite ready to buy your product or service. If you cater to their every inquiry and spend hours replying to those emails, messages, and phone calls, you may just outspend what they’d be worth to you in the hours spent coaxing them into buying.

The solution? Be direct, blunt, and honest about what you offer, what you don’t, and whether or not they’re a good fit. If they’re starting to drain your company’s resources before swiping a credit card, politely send them on their way and avoid the future hassle. There are hungrier fish in the sea ready to happily bite, chew, and swallow whatever you’re offering.

A lot of people are wary of businesses that advertise online, assuming they might be scammers with fly-by-night operations stealing your money and disappearing forever. In case you were unaware, the reverse exists, too — and entrepreneurs who deal with a large enough sample size of customers may one day encounter it: premediated customer scammers.

You know these people exist, and while karma may be coming their way, it could take a long while. In the meantime, they’ll be requesting refunds on perfectly good products, buying items they claim they never got, disputing transactions for services they’ve already enjoyed, and otherwise taking advantage of your products or services without paying the price.

These people believe they can win any battle or dispute if they make enough noise, shirking refund policies and assuming their bank, customer service, and Amazon (or any other marketplace that offers lenient refunds) is always on their side. These people have no conscience, and while they think they’ll always win, you don’t have to let them.

The first way to avoid falling prey to the customer scammer fate is to set clear, prominent, non-negotiable policies around services, guarantees, warrantees, refunds, and returns. The second is to keep clear documentation of every step of the customer purchase, delivery, receipt, and utility process, from tracking numbers to shipment notifications to time-stamped proof of receipt and use of digital products and services. This type of documentation can save your company from scammers’ baseless claims and keep you on the winning end, clawing back every dollar they attempted to siphon away.

If you aren’t keeping these policies clear and prominent and these customer proof records on hand, you can only blame yourself if a dispute or refund request doesn’t go your way.