The $540 software that costs three months

Last week a woman told me the software she was about to buy costs $540 a year. Then in the next breath she told me what it would actually cost her.

She's the only paid person at a small nonprofit here in the Bay. Twenty hours a week. Her board had been looking at a do it yourself CRM, and $540 a year is nothing. Everybody in that room agreed it was nothing. Then she said this:

"You guys have to be ready for me to split my time in half just for the CRM for at least three months. So that cost hasn't been put into account either."

Ten hours a week for three months. Roughly 120 hours of the only person who is pointed at a data migration instead of at donors. And nobody had priced it. It hadn't come up in a single board conversation. She worked it out herself, sitting in the meeting, while everyone else was still looking at the $540.

$540 is the only number printed on the page, so $540 is the number everyone argues about. But the person that decision lands on was sitting right there, and nobody thought to ask her what it would take until she said it out loud. Which is mad when you think about it, because she's the only one who will end up doing the work.

That's the number that never makes it onto the quote.

What small business software actually costs to set up

I've been in a lot of rooms this year where the same thing is sitting on the table, and it's never the price.

A construction firm I met spent around $250k trying to move to new accounting software. The migration was run by a project manager who'd never done an implementation before. Billing got blocked, cash flow took the hit, and outside accountants are still cleaning it up. They bought a perfectly good product and had nobody to install it.

The same nonprofit already owns a CRM, by the way. A free instance somebody stood up 15 years ago, used for a couple of years, then abandoned and never touched since. Some board members still want to make that one work rather than spend anything at all, which honestly I get, but that instance didn't die of price. It cost nothing and it died anyway, because nobody owned it once the person who set it up moved on.

A CEO I sat with in July said it plainest. Every tool his firm has bought over twenty years died of the same thing. Adoption. Staff turn over and the habits revert, the subcontractors run different systems, and the thing quietly stops getting used.

So I tell owners now that the build is the short part. Two or three weeks of actual building, then eight to ten weeks of people getting used to it, and the habits wobble around week six and again around week nine, every single time. A landscaping owner down the peninsula put it better than I ever have: the build was never the hard part.

Nobody thinks they're buying software

A buyer said this to me last Thursday, unprompted, in the middle of talking about something else:

"Everybody's like, oh, we'll just get a CRM and it will just do it all."

The workflow, they reckon, comes in the box with it. And a demo does nothing to correct that, because a demo is a salesperson driving a system that's already set up, with clean data in it, by somebody who does this forty hours a week.

Swap CRM for booking software, job management, an AI tool, whatever is sitting in your inbox this month with a discount on it. Same sentence works.

When this same buyer was comparing one platform against another I pushed back with a runner who has a broken leg. You don't switch him from one brand of shoe to the other and call it solved. She finished the thought before I got there:

"The problem still is that the leg is broken."

What actually unblocked it

Months of evaluation, three vendor conversations, quotes sitting on the table.

The thing that finally moved was a recurring reminder in a volunteer webmaster's calendar to export a CSV into a shared folder, plus a scheduled task that reads that folder on a Sunday and writes her a Monday briefing. The best tool is no tool, as I like to say! No new platform anywhere in it, and it answers the exact question she was trying to buy an answer to.

I'm not telling you never to buy software. Sometimes you genuinely need the platform, and a spreadsheet held together with hope is not a system. But you can't know which one you're in until somebody has priced the setup honestly, and the vendor is never going to be that somebody, because the setup becomes your problem the second the contract is signed.

The tools got cheap and the setup didn't

Nearly everything that shipped this month is free or already inside what you're paying for. Intuit's new AI layer is in beta in QuickBooks. Google wired 13 apps into Gemini, Angi and Thumbtack among them, so when a homeowner in Mill Valley asks their phone for a plumber the answer now comes off a listing you might not have looked at in two years. Google Sheets can build a working app out of your spreadsheet from a plain English prompt. Anthropic put a full training course online for nothing.

None of that costs an owner a dollar. And not one bit of it does anything about the 120 hours.

Before you sign anything

Get the setup priced, and not by the vendor. Ask whoever is actually going to do the work: who is doing the migration, by name? How many of their hours, in a normal week, for how many weeks? What stops getting done during those weeks? Who owns it in month four when the person who set it up has moved on?

If nobody can answer the last two, the project hasn't been costed. It's been quoted.

I do this in person and I'm 20 minutes from most in Marin. If you've got a software quote sitting on your desk right now, send it over and I'll tell you what the setup will actually cost you in hours and whose hours they are. No charge for that. And if the honest answer is that you shouldn't buy it, that's the answer you'll get.

Book 20 minutes, or email jay@jaimate.com with the quote attached.