I Fired My Software Company

Every operator I know has a vendor like this one. You signed up years ago because you needed dispatch software and they were the option everybody used. The price crept up. The product stopped moving. And somewhere along the way the monthly invoice turned into a tax you just pay for the privilege of staying in business.

Mine was $650 a month. Sixteen trucks, a real dispatch operation, and a piece of software that — by 2025 — hadn't shipped a meaningful new feature in close to two years. I'd email support with an idea. I'd get a ticket number. Nothing would happen. I wasn't a customer to them. I was a recurring charge.

The math is the part that should make you uncomfortable: $650 a month is $7,800 a year. For software standing still. And I wasn't alone — half the operators I talked to were stuck in the exact same spot, paying the exact same kind of tax, telling themselves the same thing I was. What else are you gonna do? Build it yourself?

The thing I almost didn't try

Spring of 2026 I started using Claude. Not for novelty, not to make memes — for the boring stuff that eats an owner's day. Drafting customer responses. Cleaning up spreadsheets. Writing hiring docs. Turning the way I do a job in my head into an SOP a new driver could actually follow.

A few weeks in, something clicked that I wasn't expecting.

This wasn't a chatbot. It was a tool that did real work — if you knew how to talk to it.

That's the whole turn right there. Most people poke an AI twice, get a generic answer, and decide it's hype. What they're actually running into is that they haven't learned to give it a real job, with real context, the way you'd brief a sharp new hire. Once I started treating it like a coworker instead of a magic 8-ball, the quality of what came back changed completely.

From "draft my email" to "build my software"

I'm not a software engineer. I want to be clear about that, because the temptation is to read this and assume I had some hidden skill. I didn't. I'm an operator who got dangerous in a terminal — somebody who was willing to be bad at something new for a few weeks.

But the same tool that cleaned up my emails could also write code. So I started small, then stopped being small. With Claude as my co-founder, I built the foundation of the US Tow Alliance and a suite of AI-native tools for towing — the stuff my old vendor wouldn't ship. Native mobile. Multi-tenant. Motor-club fluent. Built in days, not the months-and-a-roadmap-meeting a software company would've quoted me.

And then I did the thing I'd been afraid to do for two years.

I cancelled the $650 a month.

What I actually want you to take from this

Not "go build your own dispatch software this weekend." That's not the lesson, and anyone who tells you it's that easy is selling something.

The lesson is about leverage. The cost of building the tools your business needs just dropped to near zero — if you know how to use AI as a coworker. That "if" is the whole game. It's the difference between paying the tax forever and firing the vendor.

Here's where to start, in order:

1. Pick one annoying task you do every week. Not your whole business. One task. The email you hate writing, the report you dread.
2. Brief the AI like a new hire. Tell it who you are, what the job is, what "good" looks like, and what to avoid. Vague in, vague out.
3. Make it fix its own work. First answer is a rough draft. Tell it what's off. "Too formal." "You missed the price." "Shorter." Watch it tighten up.
4. Add up what that task costs you. Time, money, or sanity. That number is your motivation to do it again tomorrow.

Two years I told myself I had no choice. I had a choice the whole time. I just didn't have the skill yet — and the skill turned out to be learnable in an afternoon, not a degree program.

That's the part nobody's telling small business owners. So I will.