My Impressions: Best Payment Services for Running your Small Business.

Three easy set up, easy manage, payment processors that do more than accept payments.


Invoicing and receiving payments from clients is one of the primary survival needs of any business. I’ve used three main payment services over my second life in the freelance marketplace, I’ve also used the more traditional “handshake method” to varying effect. I do not recommend using that method, ever.

Of the many options I’ve test-driven, including ones offered by my local banks and credit unions, Square, PayPal, and Stripe, have proven the most flexible, inexpensive and easy to set up.

There are pros and cons with each that should be considered if you are planning to make a serious go of working for yourself. Further, there are definite benefits of one over the other depending on what you are trying to achieve.

My recommendations are based on the way I do business, I have an existing business relationship with a bank designed to work with these three options and my business accepts both online payments and in-person payments. I deal primarily with credit card and debit card payments but also take checks from those clients whom I have already screened.

All of the following services require a linking preexisting bank account. Mine being Azlo Business checking,* which interfaces with all three options. Most also require a small amount of expertise in setup processes, though most can be set up by a layman, some knowledge of linking accounts and tax information may be required.

I’ll list my preferences, in order, below:


Square has dominated the mobile POS market for a while now, their free services are many and they do some basic things in a way that feels seamless and easy to use for the average small merchant or side hustler.

One of the things I most like about Square is that they don’t charge you for a lot of the add on services that many processors do. There are modest fees involved but for the services offered Square is without peer in its ability to deliver a robust set of basic components that help you create customer lists, manage invoices and collect payments in a snap.

Square’s suite of basic CRM, Payroll, Invoicing, and reporting is tied together in an interface that can be a bit overwhelming for someone who is new to any of these functions but Square has also included a very intuitive help feature and on its homepage offers many other resources that users will find helpful.

In my time collecting and managing payments Square has the most to offer as a standalone payment processing service.

Square, as its rival Stripe, are both also getting into the business lending market. I’m honestly a little uneasy about this prospect as it removes local banks and governments as the first choice of small business owners, or further marginalizes owners who have suffered financial setbacks in their personal lives as good personal credit is often needed to secure a first business loan. My personal preference is to keep as much as you can local, I’ll talk about the reasons behind this in a later post.


A newer entry into the payment processing field and a formidable competitor to Square, Stripe is a tech darling. They were once a startup themselves and offered some innovations that Square did not, they also focus mainly on eCommerce solutions and as such are very well suited to businesses and individuals who are internet-based or contractors and consultants who manage payments and contracts electronically. Stripe and Salesforce have joined forces to enhance the CRM functionality of the product and are making headway in surpassing Square in its customer relationship functionality.

Stripe has also made some strategic moves into the nonprofit sector a cue they seemingly are taking from their partnership with Salesforce as they too have been courting nonprofits with a free CRM product.

Stripe has much of the same functionality as Square as well as the ability to run multiple businesses from the same login. Many of us are engaged in multiple business ventures, internet side hustles, and passive income streams. With Stripe, you can monitor all your ventures with the same login.

Where Stripe still needs polishing is its interface and its offerings for customizable billing options, where it excels is in areas of possible growth. It seems in a way, like a product in permanent beta and that is both a good and bad thing. Good because the team at Stripe is actively engaging its customer base in the testing, feedback and rollout of new components and bad because it feels like a product that has not been fully formed but is presented as “finished.”

If your business is primarily online, give Stripe a good hard look.


The granddaddy of payment processing for internet purchases. PayPal started out as a security company in 1998, became a part of eBay in 2002 before being spun off recently as its own company.

Aside: Peter Thiel famous for being the guy who took down Gawker and an evangelist for libertarianism is one of its founders and current CEO. (Yeah, honestly, I’m not a fan. But I did want to get that out of the way because although I find him personally distasteful, it has no bearing on my ranking or my inclusion of his company on this list)

In many ways, PayPal has been the F150 of the online payments world, reliable, (comparatively) well built and stable. That, however, also makes it slightly old, clunky and lagging a bit behind its competitors in innovation. What PayPal does do very well is that it serves as a simplistic, all in one, easily compatible across multiple platforms, stability champ.

If you have an eBay or Etsy shop, you’ve probably had lots of exposure to PayPal. If you are planning on transitioning to your own hosted site or a brick and mortar/popup store or trying to establish a brand identity, PayPal isn’t the best choice. If you are primarily reselling and/or engaging customers through an already established platform PayPal is usually the best choice for you especially if the site you are working with has a preexisting relationship with them.

The Others:

There are a few other existing and in developing online and desktop applications that serve some of these purposes but the field that was once one of the exclusive provinces of a few obscure vendors is now in the hands of non-bank actors. Many times the backbone of these systems, much like small wireless companies, either rely on the internet and existing bank infrastructure elements, or are run by the banks themselves. So, don’t cry for them, they still have a few hands in the pie-making process.

One thing is for sure, finding a low-cost payment processor for any level of business is easier, and the choices are better than ever before.

*Azlo Business Checking was a godsend to find, talk about walking you through the process and creating a path for you to get set up, Azlo really did this well. Be prepared to have all your documents at the ready when you sign up. My LLC documents were still pending and there was a slight delay because I did not have my state documents ready to upload. If you are unsure of what you need the setup process will help make that clear and you can pick right back up in the signup process where you left off after initial registration.