What Frustrates Me About Square Up


I’m going to try my best to have an unbiased view of Square Up.

It’s tough, however, to not be partisan when I talk with small businesses every single day who complain about the costs, feature overload and passive support of Square.

Don’t get me wrong – I think Square Up adds large amounts of value to specific industries likes retail, restaurants, and food trucks.

But for many of the service professionals I speak to each day (like contractors, stylists, personal trainers, dog walkers, cleaners, tutors and more), Square Up tends to have a number of core issues.

The feedback is simple: It can be really, really, really frustrating.

High, Complicated Costs

The biggest deterrent to accepting credit cards are high fees. Most business owners can relate to that.

Cash flow is very important to small business owners, so keeping costs simple and low is a must.

The pricing structure for companies like Square Up, Authorize.net and even PayPal are still stuck in the stone ages.

There are processing fees, per transaction fees, batch fees, hardware fees, monthly gateway fees, setup fees, and more. The unspoken truth is in the fine print unfortunately.

To make things even more complicated, the fee structures are different depending on how you (as a business owner) accept payment. A swipe? An online payment? An invoice payment? A card entry?

The truth is most on-the-go business professionals don’t want to have to stop and think about how much in fees they’ll be paying based on how their client will be paying using their credit card.  

Innovations in payment processing technology has skyrocketed in recent years. That means these processors should not be complicating their customers with complex pricing schedules.

There needs to be a single transaction fee…a low transaction fee.

It shouldn’t be this complicated.

Hardware Necessary

Let’s be honest – when a client is paying for services, the customer is not always right in front of the professional.

Most of the businesses we speak to each day are invoicing clients, collecting deposits, accepting online bookings/payments – they need more than point of sale credit card processing.

Square is best known for its swiping – when the client is right in front of the business owner. Because of this, hardware (or the “Square reader”) is mandatory in order to perform the very act of swiping a credit card in person (or inputting a card into a larger reader if EMV chips are involved).

In our “attempt” at humor, we published a Top 10 Ways to Ditch Your Square Reader…highlights include attaching your reader to a SpaceX rocket ship or planting it in your backyard to see what grows 🙂

Ok, back to the serious stuff...like the problems with hardware.

The hardware breaks. It doesn’t plug in if you have a smartphone case. You can’t ever seem to remember to pack it. The hardware doesn’t store the card information of your recurring clients.

What makes sense is a credit card reader at a Starbucks; or at a restaurant; or in a food truck.

Hardware can only be used in a single situation – in person. Most on-the-go professionals need more than that.

Feature Overload

Square Up touts how it helps service businesses “run their business”.

But in the real world, there are limitations to that marketing message – you need more than just a credit card processor to run your business.

For example, here’s some feedback we received from Tim who runs a fitness business:

“I am using Square Up for processing (@3.5% + $0.15 for manually entered), use Google Calendar, use Zoho for billing and have to run monthly credit card payments manually.”

So for Tim to run his business, he needs more tools (than just Square Up) with more features. He uses up to 5 other apps and tools to help him with the day to day.

To address this problem, Square has also invested in building adjacent tools and (supposedly) complementary apps.

Here’s a quote we received from Susan who runs a small tutoring business in Texas. Let me know if you can guess what her issue might be here:

“I use the Square Cash app, Square Appointments, Square Invoices, and Square Online Payments via my website.”

She uses more Square tools than just a credit card processor. However, she uses 4 different Square apps to help her run all the parts of her business.

She spends most of her time hopping in and out of each Square-built app – in many ways not any real difference from Tim’s problem above. The Square apps are not integrated, they don’t sync, and they each cost their own ongoing monthly fees or transactions fees.

A lot of frustration comes from the fact that Square Up is a payment processing company at its heart, and business owners are having fundamental issues using Square to “run their entire business”.

“I can’t get anyone from their support team on the phone!”

If I’m using Instagram, and I run into a bug or have a question, I don’t necessarily panic.

I’ll email Instagram’s support team with more of a “heads up” about the issue and not really lose sleep over it, and definitely do not expect to get someone on the phone to discuss the issue.

Why? Because I don’t rely on Instagram to survive (i.e., collect payment for my business).

But for business tools, high-quality/real-time support is something that is absolutely crucial.

What if your client is having trouble paying you? You can’t charge a credit card? You’re waiting on a deposit and want to know when it will arrive? All of a sudden your reader breaks?

Square Up has limited phone support. That means the busy professional can’t speak to a real human being on demand…A human with real feelings who can be empathetic with the fact that they’re trying to run a real business, collect actual payment and are experiencing a serious roadblock.

Am I Being Too Harsh?

I honestly don’t think so.

My concerns here aren’t made up. These are concerns that I’m echoing from real business owners, with actual concerns who are trying to each build something awesome – their own business.

Square Up is not the future of small business technology. It’s the past.

Most single small business owners don’t have a voice loud enough to make significant change in technology. So it’s on us to voice their concerns, address their issues, and come up with a practical solution.

If you have opinions on Square (similar or different to ours, either way), drop US a line directly or visit our blog.

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