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Should You Build It or Buy It? A Framework for Small Business Software Decisions

I’ve spent twenty years building custom software for companies of every size, and here’s the least self-serving thing I can tell you: most small businesses that ask me to build them something shouldn’t build anything at all. They should buy it.

That’s not a knock on custom software — it’s exactly the right tool for the right problem. The trouble is that “should we build this?” usually gets answered by momentum and enthusiasm instead of by a clear-headed look at the actual tradeoffs. Here’s the framework I actually use.

Question 1: Is this core to how you make money?

Be specific. “Core” doesn’t mean “important” — plenty of important things aren’t core. It means: is this the thing your customers are actually paying you for, or a specific process that gives you a real edge over competitors?

If yes, custom software starts to make sense, because off-the-shelf tools are built for the average case, and you are explicitly trying not to be average at this one thing.

If the honest answer is “no, this just needs to work so we can get back to the actual business” — that’s a strong signal to buy, not build.

Question 2: Does something already do 80% of this?

Almost nothing a small business needs is genuinely novel. Scheduling, invoicing, inventory, CRM, project tracking — there are mature, inexpensive tools for all of it, refined over years by companies whose entire job is that one problem.

If an existing tool covers 80% of what you need, the math almost never favors building the other 20% yourself. You’d be trading a $30/month subscription for a piece of software you now have to maintain, secure, back up, and fix forever — with none of the specialization a dedicated vendor brings.

The exception: if that missing 20% is your competitive edge (see Question 1), it might be worth a much smaller, targeted build that plugs the gap rather than replacing the whole tool.

Question 3: What does it actually cost to be wrong?

Buying the wrong off-the-shelf tool costs you a subscription and a few weeks of frustration. You cancel and move on.

Building the wrong custom tool costs you the development time, the ongoing maintenance nobody budgeted for, and the awkward conversation about sunk cost a year later when it’s clear it isn’t working. Custom software is a mortgage, not a purchase — you’re committing to payments (in time, money, or both) long after the exciting part is over.

Weigh the downside, not just the upside. “It would be nice to have it exactly our way” is rarely worth the size of that downside unless Question 1 already told you this is core to the business.

A rough decision guide

If the answer is…	Lean toward
Not core to what makes you money	Buy
Something off-the-shelf already does most of it	Buy
The cost of being wrong is high and ongoing	Buy, or start very small
It’s core, nothing off-the-shelf fits, and you can afford the long-term cost	Build

Most small businesses land in “buy” far more often than their instincts tell them to. That’s not a failure of ambition — it’s the difference between spending your limited time and money on the thing that actually makes you money, versus the thing that’s merely interesting to build.