This is a story of my experience as a merchant searching for a payment provider, the reason I believe merchants hate square customer service, what I learned, and what I did instead.

The name is Jack, or Giacomo as my nonna used to call me. I’ve been in the food business for over forty years and today I’m here to rant about Square. A payment provider with lousy customer service, fees, and policies.

You may think my Sicilian blood is getting the best of me and that my vitriol about Square is a bit hyperbolic. But by the time I’m done telling you my story, you’re going to be up in arms yourself.

So take it easy for now. Sit back and let me pour you a nice glass of Marsala. Here’s a plate of Pasta Con le Sarde—Pasta with Sardines, a Sicilian favorite. And once you’ve polished it off, I’ll bring you some cannoli and I still won’t be done with telling you how Square double-crossed me.

I’m speaking proverbially about the food of course, but if you’re ever in Boston’s very own Little Italy, pop by and let me know you read my rant…I’d be happy to serve you, on the house.

Square One: How My Business Got Started

We’ll get to Square in a minute. First, let me tell you how I arrived at Square, starting at square one (you can see I’m very much into the puns). My father and mother immigrated to this country in the late 1920s, right after Benito came to power in Italy.

“Time to get out,” my father said, even if Benito made the trains run on time. So my parents get to Beantown in 1928, right in time for the Stock Market Crash.

My father couldn’t find a job anywhere, so he did what Sicilians do best and got to work. This man literally sold cannoli on the street for five years, saving up nickels and dimes until he had enough to put down the first and last month’s rent and a deposit on a small storefront. And what did he name it… “Cannolis”, of course.

My father was one of those success stories you hear coming out of the Great Depression. By 1950, he had moved to a much larger storefront just down the street from Paul Revere’s immortalized bronze mugshot.

I remember as a little kid, how tourists used to come in for a deep dish pizza and my father used to pour them complementary glasses of Mandarinetto before giving them the rundown on his town.

Back in those days, my father collected cash and cash only. He didn’t know anything about credit cards and he for sure didn’t accept checks. And you know what…he kept it that way for three more decades before he turned the business over to me. Che dio lui benedica, he’d be rolling over in his grave if he knew what Square put our family through.

Introducing Credit Card Transactions to The Family Business

In any case, I was practically the black sheep of the family for introducing a POS terminal to the restaurant in 1986. As it turned out, Square is a POS itself, but here I am talking about a point-of-sale terminal. You know, that plastic doo-dad that facilitates credit card transactions. I figured that credit card payments were the way of the future.

Sure, there was a processing fee to take the cards. But I’d had enough of the tourists coming in with no cash and just plastic. I couldn’t serve them, so they left. That’s when I knew I needed a payment processor. In those days, I was pretty much on the cutting edge of technology. McDonald’s was just rolling out POS terminals themselves, so I was really ahead of the curve.

Over the years, I went through a few different vendors. POS features became more robust and the devices themselves became smaller. Different companies offered better terms of service to beat out competitors, or a lower monthly fee. I never like to walk out of a business arrangement, but I put the family first.

And strangely enough, that’s how I ended up with Square. The road to Hell is paved with good intentions…and if you don’t believe me, ask Dante (even if he’s a Toscano).

A Little History On Square

First, a few words about Square. It was founded by another fellow named Jack…the same guy who made that website with the bird. Couldn’t ever figure out what all the chirping was about over that thing, which is why I have my cousin run the social media end of our marketing.

In any case, Jack Dorsey invented Square in 2009 and it quickly grew to corporate-sized status in 2015, going public with its own stock. Don’t know about you, but SQ is one stock symbol I wouldn’t touch with a ten-foot pole…and just to be clear, I’m not giving you financial advice. It’s just my opinion. But I think it’s a good one.

One thing that set Square apart from its competitors was the way it marketed mobile card readers to small business owners. Business owners that are such small fish, they don’t even have a POS terminal and maybe they don’t even have a store—just a smartphone for mobile payments. That’s the type of merchant that benefits from working with Square, maybe.

To make a long story short, Square is good for merchants who process a low volume of online payments, or maybe even an in-person payment here and there. It’s not good for merchants who process a high volume of sales—you know, like a family-owned restaurant in one of America’s busiest pedestrian districts. Open every day from 9:00 AM to midnight and 2:00 AM on Thursdays, Fridays, and Saturdays.

Woman replying to emails on her laptop

How I Stumbled Across Square

But let’s go back to the beginning. The reason I looked into this myself is because of Columbus. That’s right, Columbus, the fellow who bumped right into America. As you may or may not know, Columbus Day is a big festival for Italians.

No matter what city in Italy they’re from. We decided we were going to do a popup stand for the parade and festival that year. So I looked into ways we could collect credit card payments from customers attending the festival.

My online research led me to Square of course, and you might have come across the same results (hopefully this rant will catch you in time). There were some Square competitors that seemed similar, but Square just had the easiest signup process, and let’s be honest—there’s something mesmerizing about their logo. I was instantly approved and the mobile payment card reader for smartphones was only $50 a pop.

I also liked the flat fee structure. Keep it simple, I always say—semplice. Transaction fees of 2.6% + $0.10 per transaction. Square also had some extra bells and whistles like helping with inventory management at the bar and table plan management.

We were just getting into online ordering, so Square could help with that too in terms of online sales. Wow, it was like a focaccia with all the toppings—onions, anchovies, tomatoes, and pecorino.

Square was my pick moving forward. I replaced all the POS terminals in the restaurant with Square terminals. The extra bells and whistles were like nothing I’d ever seen before. Everything seemed molto bene…until it wasn’t.

The Large Event That Caused Some Large Problems

I remember the day like it was yesterday. A lady called the restaurant at around 11:30 in the morning, sounding like she’d just climbed to the top of Mount Etna. Out of breath, she told me she was the leader of a senior tour group. They had reservations for a restaurant down the street—a good fellow I know, actually—but a pipe burst in their kitchen and they were closed for the rest of the day.

She needed an Italian restaurant that could host 50 people. I never say no to hungry people, so I told her we would of course clear space out for her. We still offer packages like this, so let me know if you’re showing friends around Boston.

In any case, our standard practice was to charge a set price for a fixe prixe menu (as they say in French), collecting half the payment upfront and half after the cannolis come out and the Mandarinetto is served.

So I directed her to the website to make her payment, no problem. I called up il capucoco (that means the chef) and gave him the rundown: 15 large Sicilian pies, thirty pounds of risotto, and enough Pasta Con le Sarde to fill up 100 plates—because I knew everyone would be asking for seconds. All day, a cool $3,500, including the tip for the wait staff (I take care of my people).

This is when things got a little bit weird. To be more precise, I went to a place not even Dante the Toscano went to when he putzed around the hot place: chargeback hell. And boy, would you be surprised…chargeback hell is not hot. It’s cold. Very cold. Cold shoulder cold—can’t get Square customer service cold.

The Chargeback Fiasco

To make a long story short, supper was perfetta—perfect. Everybody cleaned their plate and then some. I shook hands with the lady and didn’t hear back from her for a few weeks. That’s the problem, you see…she didn’t pay for the other half of the bill that week. And not only that, she called her credit card company and filed a chargeback.

Eventually, she called me back and made things right. When she finally sat down to pay the bills, she mixed us up with the other restaurant—and figured it would just be so much more polite to cancel the charge with her bank instead of bothering the restaurant owner.

Spoiler alert: it’s not…it’s a much bigger pain in the behind. So that’s what she did and busy as she is, totally forgot to pay for the reservations that had panned out—the ones she made at my restaurant.

I could barely believe what I was hearing, but I wasn’t going to make a stink about it. Besides, by the time she called to make things right, I had already suffered through my experience with Square. And boy, did they make me one unhappy merchant.

A few mornings later, I came in for business as usual. We got to work wrapping up silverware, brewing coffee, kitchen prep, table prep, and everything you do in the morning. At 10:00 AM, the first customers started coming in for coffee and cornetti—and don’t you dare call it a croissant.

The Frozen Merchant Account

The first customer tries waving their plastic over the POS. No go. They stick the chip in. They swipe it. I take the card and blow it off. I do all the same stuff they did. Nothing. Okay, no problem, I figure. Cornetti and coffee on the house and let’s figure this out before the next batch of customers come in here.

What I figured out was that Square had frozen our account and locked us out of taking payments. And what’s more, I had no idea why. Keep in mind this lady with the tour group had just come in the other day.

I had no idea she had filed a chargeback. Square just froze our account, without telling me anything. Finally, I got an email from them telling me that a sizable chargeback had been initiated against the group dinner charge.

Here’s the thing I learned about Square. Square merchants are all batched under Square’s own merchant ID number. And Square doesn’t want beef with any bank. If any of the merchants using Square do anything shady, Square will drop them like a hot ravioli.

Then they’ll let you know that due to some high-risk activities on your end, you’ve got to find a high-risk merchant account. If you have any questions, get in touch with their support team, please, and thank you.

High-Risk? You’ve Got the Wrong Guy

Before I talk about the support team, let me just explain a little more about high-risk businesses. I have been in this business for almost four decades myself, in addition to the time my parents put into the restaurant.

This ain’t no bail bonds place, it ain’t no health supplement store, it’s nothing shady. Those types of businesses do need a high-risk merchant account, and I know that from talking to some friends who are in those lines of work.

But the food business inherently is not any kind of risky business. This is a family joint, serving real Italian food. There are no Godfather kind of business deals going on over a plate of pasta fazool. Just food, love, and a whole lot of parmesan.

However, you can be considered a high-risk business if you get an excessive number of chargebacks—which has never happened to us—or if you get hit with one massive chargeback that knocks your usual transaction size outta the park.

Well of course $3,500 is not our usual tab. This must have set off all kinds of alarms over at Square. I get it, in a way: chargebacks create an avalanche of fees that the bank and the payment processor, and the card network all have to deal with, before dumping it on the little guy (me).

Confused woman in front of a laptop trying to contact customer service

Contacting Square’s Customer Support

So I looked up the phone number for Square credit card processing. I figure this is going to be easy. Merchant services like Square are all about collecting money, right? And if you’re in the business of collecting money, you get on the phone real quick.

Not Square. From the time I dialed the Square merchant services phone number to the time I spoke to a real, live person, I’d estimate about two hours went by. I’m not kidding. In the meantime, we took a page out of the playbook of what made this business work in the first place: thinking on our feet.

We put up a sign that said CASH ONLY and moved on with our day. Sure, we might have lost about 15% of our sales, but we were able to keep our doors open. There were some grumblers and whiners, but a little complimentary Mandarinetto washes everything down real nice.

So finally I’m talking to a real person over at Square Payments customer service. Maybe a lot of other merchants were dealing with chargeback hell that day…who knows. If you’ve ever read about how to get in touch with Square, or Square processing reviews, you’ll see I’m not the only one who has had this experience.

The agent tried to be helpful, but they couldn’t say much other than explaining to me that a massive chargeback had occurred and I was probably going to see my Square deactivated.

Other Merchant’s Complaints About Square

At that point, I decided I didn’t need to wait around for Square to be deactivating my account. I decided it was time to look for an alternative to Square. If you’re in a high-volume business like mine, you cannot, cannot, cannot have your ability to take payments offline in the middle of business.

I sat down at my desk and started looking for a Square alternative. That’s when I started reading Square merchant services reviews and seeing that a lot of people were writing about how frustrated they were with Square, particularly its customer service.

They couldn’t find the Square processing phone number easily. If they found it, they couldn’t get a hold of a live person. If they got hold of a live person, that person didn’t know anything. Some customers just got a notice that they had been deemed a high-risk business and that Square would be pulling their services—sort of like what happened to me.

Looking For a Square Alternative For Payment Processing

It took me about two days and a whole lot of conversations over Bocce Ball, but I learned something from my colleagues in high-volume businesses. They told me they would never, never work with a company like Square and that the best alternative to Square was a payment processor that provided them with a dedicated account manager.

You know, a real live person you can get in touch with when the sauce hits the fan. No monolithic flat rate pricing, no outsourced customer service. Tailored payment processing plans and fees that fit with your business. Companies like Square are great for small fish, but if you’re handling lots of payments every day, Square is not for you.

That’s when I got in touch with ECS Payments and things have worked out well with them. As I mentioned, that lady eventually called me back and paid me in full. A blessing in disguise you might say—and I didn’t mind telling her either. Or you.

Start saving on payment processing today!

In summary, I would say that the biggest reason I hated Square is because of its customer service. That alone was enough to make me look for an alternative to Square credit card processing. Square just doesn’t treat you like family.

It sounds hokey and we all know it’s a business arrangement. But the people you do business with have got to be able to pick up the phone and give you some straight answers when you need them.

Square didn’t do that and that’s my beef with them. So now you’ve heard my story and I want to thank you for listening. Next time you’re in Boston’s Little Italy, stop by Canolli’s and I’ll pour you a shot of Mandarinetto. And if you’re in the business yourself—any kind of business—stay away from Square!

To contact sales, click HERE. And to learn more about ECS Payment Processing visit Merchant.