Build vs Buy Software: 2 Questions for Every Contractor

October 2, 2026

This is the video behind the post. It walks one roofing crew through all 3 steps, so you can see the 2 questions work on real tools before you try them on yours.

Build vs buy software comes down to one rule: rent what’s the same for every business, build how you win the work, and make the call yourself instead of letting a sales demo make it for you.

That’s the whole idea. The rest of this post is how to use it on the tools you already pay for.

The problem isn’t the software

A salesperson walks you through a slick demo, and you say yes. A few months later you’re still paying for it every month. Nobody on your crew opens it. And the way you win jobs is stuck inside it.

Most owners think the question is which app to buy. It isn’t. The question is what your business should rent, and what it should build.

This isn’t anti-software. Use plenty of it. The problem is paying for tools you don’t understand, and handing the part that makes you different to somebody else’s app.

So the rule has 3 parts, and they go in order.

Step 1: rent the commodity

A commodity is anything that’s the same for every business. Bookkeeping. Email. Card payments. Your phone.

Think of the phone. Nobody wins a job by reinventing the phone.

So for every tool you pay for, ask 1 question: “Is this the same for every business?” If yes, write rent next to it.

Here’s why it works. If every business has it, it’s rarely the reason a customer picks you. The mistake is trying to make your own version. The right move is to rent a good one and move on.

That’s your rent list. Keep it, you need it in step 3. (Step 1 in the video)

Step 2: build the advantage

Your advantage is how you win the work. How you follow up on a quote. How a call turns into a paid invoice.

2 restaurants can buy the very same oven. The recipe is why you go back to one of them. The software is the oven. The way you work is the recipe.

So for the work that wins you jobs, ask a second question: “Is this how I win the work?” If yes, write build next to it.

In the video, Marco runs a small roofing crew. His quote follow-up was going out as the same message every roofer gets, straight from his app’s template. That hands away the way his business wins work. The right move: he writes the follow-up his way, then lets the app send it.

And if a tool does both? Rent the app, and build how you use it. That’s the answer for most of the software a trades business runs on. (Step 2 in the video)

Step 3: own the decision

You wouldn’t let a car salesman decide which car you need. Don’t let a demo decide how your business runs.

Take out your rent list and your build list. Pick 1 tool you pay for that you’ve never really questioned. Then run both questions, in order:

First, ask: “Is this the same for every business?”
If not, ask: “Is this how I win the work?”

Write rent or build beside that tool. Writing it down helps you decide, instead of drifting into another renewal. And if it belongs on the rent list, that’s fine. Keep renting it. (The 2 questions in the video)

There’s a short 8-bit version of this step. Bip’s boss rents an invoice app, which is fine. Then she picks the plan that says EVERYTHING. 5 months and $445 later, she has used 1 button. Renting was never the mistake. Renting more than the job needs was: Bip’s Boss Paid $445 for 1 Button.

Owning the decision also means knowing where your data and your logins live when you rent. The Canadian Centre for Cyber Security keeps a plain list of baseline security controls for small and medium organizations that’s worth a read before you sign up for the next app. If you’re in Canada, the federal Canada Digital Adoption Program page is another place to see how small businesses plan their tech.

Why the order matters

Rent the commodity. Build the advantage. Own the decision.

Skip step 1, and you build what you should have rented. Skip step 2, and you hand away how you win work. Skip step 3, and someone else makes the call for you.

Try it on your own tools

Here’s your move for this week: write down the one thing you most want working in your business, and decide if it’s rent or build. That one answer changes what you do next.

Not sure which thing that is? Which business problem to fix first shows you how to pick it by what it costs you, not by what bugs you most.

If you want help with it, the full lesson and a prompt that walks you through this on your own business, one question at a time, are free in my Skool community. It’s lesson 1.2 in Start Here. The lesson also has What Am I Paying For, a check you paste into Claude, the AI assistant I use, that adds up what your software costs you a month and a year.

One thing we learned building it: an AI chat isn’t a calculator. It writes the number that looks most likely, so on a long column it can slip a digit and still sound sure. So we took the adding away from it. The AI reads your statement, and a small script we wrote does the math, the same way every time. Claude needs code switched on to run it (Settings, then Capabilities). If it’s off, Claude adds it by hand, marks the total “added without a calculator, check it”, and you add the column on a calculator.

And if you’re ready to hook your phone up to a tool you rent, the Claude + Airtable setup is the next step: Airtable is the rented database, and the way you price a job is the part you build.

More at thevlway.com.