How Frictionless Invoicing and Payments Pays Off for These 2 Solopreneurs

For many entrepreneurs looking to launch their small businesses, payment processing fees can feel like a huge cost. What they sometimes forget to factor in is the unseen cost of getting paid manually: hours chasing missed payments, awkward phone calls or emails to follow up, unpredictable case flow, and reconciling books. 

That was the concern of Jon Murray, who was working as a coordinator for Maine Health’s medical alert program when he saw an opportunity to expand his services by starting his own business. 

“I quit my job, and I jumped in, scared to death, but I knew in my heart I knew it was a good move,” says Jon. But before he even launched his business, Maine SafeResponse, he knew he’d need to have a solid payment solution.

As a small business that provides 24/7-monitored medical alert systems, Jon has a subscriber base of over 50 people with hundreds more on the way. That’s a lot of invoices that need to get processed and paid monthly—on top of an exhaustive list of other administrative and job-related duties, including traveling to meet with clients who may be up to 40 miles away from his home base.

“I am running all over the place. I’m extremely busy, and it can stretch me really thin,” explains Jon. “Trying to mail invoices would have been a nightmare. I also didn’t want to be chasing people around trying to get them to pay their invoice.”

Jon knew from the outset that his business couldn’t run on manual payment collection. But it’s not unusual for many new business owners to get caught up in the momentum of launching their business. So setting up a formal payment processes tends to fall down the to-do list, with owners often making do with the tools they already have—like tracking payments in spreadsheets, emails, or even just in their mental notes. But over time, the temporary and often manual solution starts to compete with the work they’re actually getting paid to do.

It’s a story that AI and digital growth strategist Leann Reagin knows all too well. 

Leann’s temporary solution wasn’t a spreadsheet, but rather a combination of PayPal and her memory. The process for getting paid was multi-step—it required her to receive money into her PayPal account, then transfer it into her bank account, reconciling as she went. Seeing who hadn’t paid and who had to be reminded was a manual process—one that left her with little time to hunt for a better option.  

Frictionless pay—for business owners and their customers

Fortunately, the answer arrived courtesy of a “professional-looking” invoice created by a colleague in FreshBooks. Leann immediately realized that it made what she’d been using look “tacky” in comparison, and she started making the shift to FreshBooks. 

But it wasn’t until she’d been on the platform for 4 months that she started exploring its payment features. “I believe I just got an email about the Stripe add-on, and I just decided to try it out and see what happened,” she recalls. “It was a happy surprise.”

 “When I saw that Stripe puts the money directly in your bank account, I was like, ‘this is awesome!’” 

Jon had a similar experience.

“I don’t have to hunt people down for invoices if they forget to pay. And if a credit card payment gets declined, I get that alert, and I’m able to take care of it quickly,” says Jon, who signed up for FreshBooks after taking a trial. Today, it acts like his administrative assistant, making hectic days feel a bit more manageable. From the road, he’s able to set up new clients in the system and process their first payment on the spot. It’s more than just an accounting software—it’s a whole business solution. 

“Once a client is entered into FreshBooks and set up for a recurring invoice, it really helps me out to have everything automated,” says Jon. “It’s so much easier to deal with the other stuff I have to deal with again, knowing I can just walk away and everything's going to be taken care of.

A simple people-based solution

For Leann, gone are the days of relying on her memory—or having to follow up with her clients to get paid. Instead, she tracks her time with the FreshBooks time tracker tool, which connects directly to invoices. And if a client is late to pay, the system automatically sends an overdue reminder—freeing up Leann’s time and memory for more important things, like projects for her clients. 

Excel spreadsheets may seem basic and straightforward. Yet, “simple” is the word that both Jon and Leann use to describe FreshBooks. 

“It makes [payment] go smoothly,” says Leann. “I like how FreshBooks is laid out in an analytical way. You know how much money came in, how much you had to pay for things, and you can break it down, month-by-month.”

It’s this simplicity that has allowed both Jon and Leann to create a predictable cash flow, saving them time, reducing friction, and allowing them to focus on what matters most: Building relationships and providing great service to their customers. 

“My biggest deal is making sure that we’re treating each other with an honest and fair relationship,” says Leann. “I think it would make every business thrive.”