We’ve Had Software Backward for 30 Years

Count the software subscriptions your company pays for every month. Now count how many of them actually fit the way you work.

For most small and medium-sized businesses, that second number is close to zero. You found something that did 70% of what you needed, signed up, and learned to work around the rest. Then you bought another tool to fill the gaps.

That’s been the deal for 30 years. The software company decides how it works, and you adapt. I think that deal is breaking, and I’ve seen something like this once before.

I started my career as a web developer around 1999, selling $500 websites to pizzerias and other small businesses around Western New York. My pitch was simple. The owner could log in and update their own website. Change the hours, post the weekly special, whatever they needed. No developer required.

That was a pretty big deal in 1999.

Back then, changing a website meant knowing HTML, finding files on a server, and uploading them with an FTP client. If half those words mean nothing to you, that’s exactly the point. Most business owners had to pay someone like me every time they wanted to change anything.

I had built something that gave them control over their own websites, and I sold it one pizzeria at a time.

In hindsight, I should have sold the platform itself to other developers. A few years later, WordPress came along and made editing your own website completely normal.

I like to joke that I could have been WordPress before WordPress and that I’d probably be retired by now.

Realistically, a lot of other things would have needed to go right for that to happen, but regardless, I missed something important. I was so focused on selling websites that I didn’t appreciate what I’d actually built. The valuable part wasn’t the website. It was giving people the agency to do what previously required a specialist.

I think we’re at another one of those moments. Except this time, it’s not just websites. It’s software. And eventually, a whole lot more.

That’s why I’m starting this newsletter.

Welcome to The Great Reversal.

How we got here.

I’ve spent a good chunk of my career building and leading software companies. I know why it works this way.

Software has traditionally been expensive to create and relatively cheap to copy. Companies build one product, sell it to thousands of customers, and spread development costs across them.

The catch is that thousands of businesses have to use essentially the same product.

The software company decides how it works. You adapt your business to fit.

But what happens when building software becomes cheap enough that you don’t need thousands of customers to justify the cost?

That’s the reversal.

Instead of changing how your business works to fit the software, you build software that fits how your business works.

And this isn’t some distant prediction.

I just watched it happen.

The owner of a small infusion clinic was paying more than $200 a month for Vagaro, a subscription platform used by salons, spas, and other appointment-based businesses.

It’s not a bad product. It just wasn’t built for her business.

She ran her clinic using software designed for a very different operation. Square peg, round hole. She was paying every month to work around somebody else’s assumptions, including features built for other customers that didn’t apply to her.

So I built her something else.

In a little under two weeks, I created a system tailored to how her clinic actually operates.

She’s now paying less than she was before, and the savings alone are expected to cover her initial investment in less than a year.

And instead of waiting for a software company to decide whether her needs matter enough to make it onto their roadmap, she has software built around her business.

Now, I don’t want to pretend every business can replace every subscription in two weeks. That’s unrealistic.

Getting a working application built has become dramatically easier. Keeping it secure, protecting customer data, and making sure it still works a year from now are different challenges. Those things still matter… a lot.

But I’ve spent thousands of hours over the past two years building software with these new AI tools. I’ve watched the amount of work required to create useful, custom applications collapse.

The infusion clinic isn’t a hypothetical example of what might be possible someday.

It’s a customer who’s already saving money and using a tool perfectly suited for her business.

So what should you stop paying for?

I’m not suggesting you fire up an AI coding tool this weekend and replace your accounting system or electronic health records.

Some software is worth renting. Your financial records, patient charts, payroll, and other systems where security, compliance, and reliability carry serious consequences are often better left to established providers… for now.

But there’s another category worth looking at sooner rather than later.

The scheduling add-on. The form builder. The reporting dashboard. The three tools held together with duct tape and an automation subscription.

The software that manages how your particular business works.

That’s where things get interesting.

Here’s the way I’m starting to think about it:

Rent the systems that carry the risk. Question the systems that dictate your workflow. Own the systems that make your business different.

It’s not a universal rule. Exceptions exist, and the economics won’t work for everyone.

But it’s a better starting point than assuming every business problem needs another monthly subscription.

The question used to be, “Which software can we afford, and how do we work around it?”

I think the better question now is, “Which of these subscriptions would we still choose to pay for if building our own was a realistic option?”

For a growing number of businesses, it already is.

And that’s just the beginning.

We’re so used to software being an app with screens, menus, and buttons that we assume that’s what software has to look like.

But what happens when an AI agent can just do the work for you? Or create a screen for exactly what you need in that moment, then throw it away when you’re done?

Imagine asking your software which customers haven’t been back in six months. Instead of navigating five menus and building a report, an agent could pull the information together, show you what matters, and help you decide what to do next.

No permanent dashboard required.

Some software will always need predictable, consistent interfaces. But a lot of what we call an application today is really just a collection of screens we’ve learned to navigate because there wasn’t another way.

We may be heading toward a world where software isn’t just built for your business. It’s built for whatever you’re trying to accomplish right now.

That’s a bigger conversation for another day.

We might not just be changing who gets to build software. We might be changing what software actually is.

Why I care about this

I’ve watched small businesses struggle to compete with big companies for most of my life.

The big guys have always had advantages. Bigger budgets, more people, better technology.

They could afford software built around exactly how they operate. Everyone else rented whatever was available and made do.

I think that advantage is starting to erode.

A small business might never outspend a large corporation, but it can decide on Monday and try something new by Friday. No committee. No eighteen-month implementation project. No waiting for a vendor to decide its needs are important enough.

For the first time, a little shop down the street can realistically have technology designed specifically for the way it does business.

That’s a much bigger deal than saving $200 a month.

And it takes me right back to those pizzerias in 1999.

The lesson I missed wasn’t that I should have built WordPress.

It was that when technology stops requiring a specialist, the people who used to depend on that specialist gain control.

I watched that happen with websites.

Now I’m watching it happen with software.

And I suspect software is only the beginning.

I missed this once. I don’t intend to miss it twice, and I don’t want the businesses in my community to miss it either.

That’s what The Great Reversal is going to be about.

Every week, I’ll dig into what’s worth building, what’s worth keeping, and what to watch out for. I’ll share things I’m actually building, look at the economics, and occasionally push back on the AI hype, including my own.

Because I don’t think every business needs to become a software company.

I think we’re getting to a point where they won’t have to depend on one for everything.

Let’s start with you.

What’s one piece of software your business pays for every month that you’ve never quite liked?

Hit reply and tell me what it is and what bugs you about it.

In an upcoming issue, I’ll pick a few examples and walk through whether I’d keep paying for them or consider building something better. No names unless you want them.

Maybe the answer is to keep the subscription.

Maybe it isn’t.

I think it’s time we started asking the question.