Sense with Cents

I wrote recently about why we hung up the phone in 2019. That piece was mostly about the channel — phone versus email. This one is about the people on the other end of it, and how that has changed over forty years.

A quick caveat before the dates: the eras below have soft edges. Nothing flipped on a Tuesday. Windows 95 did not reorganize our support calls the week it shipped; it happened gradually. And we kept the phone live for a good decade after we probably should have retired it. Dates are landmarks, not hard lines.

One more thing while we are setting expectations: these are my memories. Sometimes jumbled, sometimes out of order, occasionally wrong on a small detail. This article is not about being perfect — it is telling a story. If you were there and remember a piece of it differently, you are probably right, and the shape of the story does not change.

1984 to about 1995: two experts on the line

In the early days, through the DOS era and into the first half of Windows 3.1, the person calling Medlin was almost always two kinds of expert at once. They were a computer expert, because owning and operating a computer in 1984 required it. And they were an accounting expert, because the software was doing accounting, and nobody was trying to learn that from a floppy disk.

Support in that era was mostly lending a hand. Someone who already knew both payroll and computers was moving from paper or from another system to ours, and needed a nudge on where we put a particular function. Most of the year, a portion of the day on support was enough to keep up — the rest of the day was development. During tax season it flipped: support took the whole day, and a new caller was waiting the moment we hung up the last one.

If anything, the most technical questions in those days were not about our software at all. They were about printers. Dot-matrix printers needed specific escape codes to line a W-2 up correctly on a pre-printed form. We kept stacks of printer manuals on the desk and got pretty good at translating between brands. When Windows came along and finally took over printer drivers, that whole category of support call quietly went away. We did not miss it.

The calls were also longer than what we have now, and that was part of the value. We had time, between contacts, to actually talk — about the software, about features people wished it had, about how they were running their business. I still have a folder somewhere with letters customers mailed in, suggestions written out by hand. Real relationships came out of that. Gerald in Bemidji. Stu on Staten Island. The folks in Artic, Washington — partway through a long road trip we pulled into their campground and ended up staying a few days to rest and recover. Ate next door at the restaurant their neighbor runs, also a Medlin customer. You do not get that from a ticket queue.

That habit has stuck. When we travel, we still look to see if there is a customer in the area, drop an email ahead of time, and sometimes arrange to meet in person. The most fun version is when the customer runs a retail shop, a restaurant, or somewhere else we can return the favor and give them our business.

Sometimes the encounter is not planned at all. The family was in Kanab, Utah for a greyhound event — adopted ex-racing dogs. While lining up for the parade through town, we happened to be standing right in front of a customer’s office. Small world. Forty years of customers means there are not many road trips where the answer is no.

Windows 95 forward: the computer became an appliance

Somewhere around Windows 95, computers stopped being something you had to be an expert to own. That is a good thing for the world. It is a harder thing for software support. The typical caller was still an accounting expert, but the computer part of the equation had softened. Support morphed into helping people install the software, get it opened, and find their way around Windows itself.

We were, for a stretch, as much a general computer help line as a payroll help line. Not because we wanted to be — because the person on the other end had a payroll deadline and no one else to call.

The relationships were still personal, but the winds were changing. We had to become more task-focused, less chatty. There was not time anymore to hear how the business was doing before getting to the question. This was a tough stretch. Some days the phone never stopped — we would take it off the hook to grab a bite or use the bathroom. To this day, when I hear a ring tone close to my old Plantronics wired headset, I still jump a little. The headset itself is probably still in a cabinet somewhere here.

My kids were around sometimes, and they learned to watch for the blinking red light on the mic — that meant a customer was on the line and they needed to be quiet. Observant little ones. They picked up on it without ever being told twice. Or they would come up quietly and tap me on the shoulder, and I would wave them off — sort of the way you see a finger go up now to mean “not right this second.”

They also looked forward to “coming to work” at mailing season. Most updates still went out on disks, then CDs. Sticking labels, refilling the printer with paper, watching the paper folder do its thing, playing with the piles of postcards in those white USPS trays. Hand a kid a sheet of thirty labels to stick on postcards and you have made their afternoon. Six or more people around a big table, sticking, stacking, chatting. By that point it was the Pearson kids on label duty — the Medlin kids had done their own turn and aged out before the 1993 season. Truth be told, I was mostly just visiting that table — I was downstairs on the phone taking orders, processing them, and handling support, while the Medlins entertained my kids, their honorary “test grandkids.” That merging of the two families happened naturally and fast, and it has lasted to this day — both families now have grandkids of their own coming up.

Today, and the road ahead

Now, when someone writes in, they are usually one of three people.

The first is the expert. Often a bookkeeper or CPA handling payroll for multiple businesses. They know payroll cold. Their questions, when they have any, are sharp and specific — a tax rule corner case, a new state filing, a setting they want to confirm. These exchanges are short and efficient. Both sides know the vocabulary.

The second is the DIY business owner. Fully capable of handling their own affairs, running a real business, often switching to us because what they were using before got too expensive, too complicated, or both. They are not payroll experts, but they understand their own payroll. Their questions are usually the ones you would expect at first use — where is this, how do I do that — and once they have run a few cycles, we barely hear from them.

The third is the group we spend the most time with, and it is the one that did not really exist in the old days. These are people hoping the software will teach them accounting. Not payroll specifically — accounting, in a general sense. They are not sure what belongs where, whether a payment is an expense or a liability, what their own prior bookkeeper was doing. They picked our software because it looked approachable and affordable, and they are trying to figure out the job itself at the same time they are learning the tool.

For the first two groups, the software really does self-explain most of the time. Our job is mostly helping people get over the hump of using new-to-them software, and then digging into the deep payroll issues of the day — like “no federal tax on some overtime,” which is not exactly what we all read in the media. The headline is short. The actual rule, the thresholds, what counts and what does not, takes longer to explain.

While I no longer process every order by hand, some names still catch my eye. A name from a past chat or email. A town I know. A business name that triggers a memory. When the timing is right, I will send a short personal reply just to share what caught my eye. It takes me back to the phone days, when most of this work had a personal layer. The customer often does not reply, and that is fine.

My own kids could probably handle support today. They have heard everything I have heard, and they know most of the common issues by heart from being around all those years. The Medlin kids are circling back into the company in different ways. We are all thinking about who will eventually retire me — the way I sort of retired Jerry back in the 1990s. Not forced out, never. Just someone catching on, learning enough, and growing into the work until retirement is actually possible. We are working on setting that up in the way that is best for our three families — which, the way we have always thought about it, includes our customers.

What we are working toward acknowledges that things have changed. Jerry and I each ran what was mostly a one-person shop. Over time, Jerry added me. These days I have support from others too. And the tools have changed — remote access, internet anywhere, and now AI. We are, and remain, a family business — that part is not negotiable. The old hard part — the coding — is likely the easiest task on the list today. The expertise, built up over forty years, was and remains the real value.

Honestly: I am one of the last of a particular kind, the self-taught expert at many tasks. I value those experiences. I am not trying to force them on anyone else. We are not looking for another me — there are not many of those around, and the work probably should not rest on one person anyway. We are dividing the functions into the kind of roles where today’s professionals actually thrive. That is a better fit for the workforce as it exists.

None of this is theoretical. Part of why the company has lasted forty years is that it has not been a one-person shop in the ways that matter most. Payroll experts are available to direct coders. Both types can be called on as needed. Management is in place when it needs to be. There is more here than just me — that part is also by design.

The software is the first filter

Since day one, our goal has been for the software to speak to you. The menus are in plain language. The on-screen prompts tell you what the program is about to do and what it needs from you. Our view is that nobody should have to read the manual to run payroll. That was a design principle in 1984 and it still is.

That design choice does something useful beyond the obvious. It acts as a gatekeeper. If someone writes in asking what COA means, we can be fairly sure they have no training in accounting, and our software is unlikely to be a good fit.

Not because our software is hard — it is not — but because it assumes you know the basics of what you are doing. It is a tool for people who do the job, not a course that teaches the job.

We try to say that honestly, and early. Spending a month trying to learn accounting from tooltips will not end well, and it will not end well because of us, even though the real problem is the mismatch between the tool and the training.

The paradox is that the group we spend the most time with up front is the group we are least likely to keep long-term. That is on purpose. A ten-minute exchange that saves someone three months of frustration is a good ten minutes, even if it ends with us pointing them toward a small bookkeeper down the street.

That said — the software can help you learn, if you are willing to put in the effort. My very first payroll had no PC and no software at all — just me, paper, and the tax booklets. Later, with software in front of me, the work got faster, but the underlying rules were the same ones I had already worked out by hand. The fundamentals live in IRS Publication 15 and your state’s guidebook. They always have.

What we have found, in forty years, is that most business owners do not have time to sit with those books the way I did. Which is where we can step in: not to teach payroll from scratch, but to help get someone set up to a reasonable starting point, and to review the setup once it is in place. There is a difference between learning the work and getting a hand pointing at the right place to start.

What we usually suggest, when this comes up, is a path rather than a no. Hire an accounting or payroll service to start. Let them run things for a quarter or two. Take the reports they produce and study them — that is your real training material, because it is your own business’s numbers and you already have context for what they mean. Even better, find a small local shop and be upfront with them: tell them you want help getting started, that you will likely keep them on for periodic review, but that day-to-day, you intend to handle this yourself. A small shop is much more likely to take that arrangement seriously than a large firm, and you both end up with a relationship that fits. A civic club helps too — Rotary, Kiwanis, Elks, your local chamber. You will end up in a room with other small business owners who have already worked through what you are stuck on, and the advice is free.

Once you can read your own reports without flinching, the software will make sense. Then we are a good fit. Trying to skip that step and learn accounting from the software almost never works.

What has not changed

Forty years of customers, three distinct eras, and a few things have stayed the same.

The answer still comes from someone who wrote the software, or works closely with the person who did. The support is still free. And the unspoken goal is still the one Jerry Medlin set in 1984: make the software clear enough that most people do not need to ask. When someone does need to ask, make the answer worth reading.

One quiet thread runs through all three eras: support has rarely been about Medlin itself. In the DOS days it was printer escape codes. In the Windows years it was helping people install software and find their way around the operating system. Today it is the payroll rule of the day. The software, by design, has stayed quiet enough that the questions are mostly about everything around it.

The rest is just keeping up with who is on the other end of the line.

A note in closing: this ended up Medlin-specific, but the shape of it is not unique to us. Any small family business that has been at it forty years will have its own three eras, its own customer-friends, its own kids who learned to read the room. The names and the dates change. The story rhymes.

See also: How Many of Me Are Left?, Why We Hung Up the Phone, DIY Payroll vs. Payroll Service, and Help Me Help You.