Red flags when hiring a software company (I paid for these lessons)

Before I ran a software company, I was the customer. At my last business, our website was managed by an agency, and I want to walk you through what that was like. Partly because it’ll help you spot the same patterns, and partly because how I run Mainland now is more or less a list of things I promised myself I’d never do to a client.

The billing clock

The headline feature was 24/7 support. What that meant in practice was $500 an hour if you needed anything after hours.

Meetings were their own experience. I’d join a call, count the heads, and do the math in real time. Four people on today. That’s $600 an hour. And now I’m not thinking about the project at all, I’m thinking let’s wrap this up quick.

Sit with that for a second. Their customer was trying to end meetings early to stop the bleeding. When a meeting costs that much, it had better produce decisions, and most of these produced updates.

The four-hour word

The one that finally broke me: I wanted one word changed on a page.

Here’s the route that request took. First I paid for the project manager’s time to talk to me about it. Then their time writing it up as a ticket in Jira. The ticket went to a programmer. The programmer had a question, which couldn’t come to me directly, so it went back through the project manager, billed again, and then back to the programmer with the answer. Eventually, the word got changed.

The invoice worked out to about four hours at $150 an hour. US dollars.

Four hours. One word.

The real cost isn’t the invoice

Here’s the part I want you to notice, because it’s the actual damage: I stopped asking for things.

I wasn’t happy with the product. But I didn’t want to keep paying to improve it, because the price never matched the value. So the site just sat there, slowly getting staler, while I quietly worked around it.

That’s the failure mode with the wrong software partner. It’s not one big blowup. It’s a slow freeze, where improving your own tools stops feeling worth it. If you’ve ever caught yourself thinking “I’d love to fix that, but it’s not worth the hassle of asking” — that’s the flag. That feeling is the invoice you can’t see.

What good looks like after launch

When someone builds you software, launch day is the middle of the relationship, not the end. Here’s what I think you should expect, from anyone:

A proper walkthrough and training, so your team actually uses the thing instead of the three features they discovered on their own. A warranty that makes sense: if something we built breaks, fixing it is our problem, not a billable adventure. Small changes staying small — a word change is a quick message, not a project with a ticket trail. And someone checking in because they want the product to get better, not because a retainer needs filling.

None of that is generosity. It’s just what aftercare is supposed to be.

Meetings and billing, specifically

If you run a business, you’re busy. A meeting should exist to make a decision or unblock work. Short, only the people who are needed, and you leave with things decided. If you ever find yourself counting heads and multiplying, you’re in the wrong room.

Billing is simpler than agencies make it: every hour should map to something you can point at. “SEO audit — 3 hours” with no audit attached isn’t billing, it’s trust erosion. If there’s an audit, you get the audit.

Why I actually care about this

Small studio math is different from big agency math. An agency’s incentive is billable hours; the meter running is the business model. My incentive is that your software works and you come back — the next project, the referral, the case study. Your success is directly linked to mine, which is why I listen, keep in touch, and keep improving things. Not because it’s noble. Because it’s how a small company survives.

So if you’re vetting a software company, ask what happens after launch. Ask what a small change costs, and what route the request takes to get there. Count who’s in the meetings.

And if you’ve already got that “I stopped asking” feeling with your current provider — that’s not normal, and you shouldn’t have to live with it.

I don’t want to be them. That’s most of the business plan.