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Field notes

Plain talk about the software your business runs on.

Over twenty years of lessons on building, running, and betting your business on software. No jargon, no filler.

Featured · Custom tools

What I let AI do with my inbox, and what it never touches

I built AI triage for every inquiry and support request my business gets. What it does, what it's never allowed to do, and what broke on the first run.

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Cover image for “When to replace your business website, and what it costs”
Growth

When to replace your business website, and what it costs

Most old websites don't need replacing. Some cost you money every month they stay up. How to tell the difference, and what a new site costs.

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Strategy

Moving 340 dealerships to new software, one at a time

We moved 340+ dealerships onto a rebuilt platform without a weekend shutdown. How the switch worked, what went wrong, and what to ask your developer.

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Strategy

How to Hire a Developer When You're Not Technical

You can't read the code and you don't need to. What to check before you ask for a quote, what a good first call sounds like, and when to walk away.

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Strategy

When I'll tell you to rebuild it

Last week I argued that most old applications don't need rebuilding. That's still true, and it isn't the whole story. Three situations where starting over is the honest answer, one that gets mistaken for them constantly, and the part of a rebuild that actually goes wrong.

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Strategy

The rewrite you were quoted isn't the only option

An old application that's slow and full of small bugs usually gets one answer: rebuild it. That answer is often wrong, and it's the easy thing to quote. This is what happened when we upgraded one instead, three months, 40% faster, and the two questions that tell you which situation you're actually in.

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Strategy

Nobody taught you how to read a software quote

Three quotes for the same project, at wildly different prices, and no way to tell which one is honest. That's most people's experience of buying software. What the spread actually means, why the cheapest and the priciest are usually both wrong, and the questions that sort it out.

Cover image for “The burglar alarm I built after the burglary”
Strategy

The burglar alarm I built after the burglary

The 97-day break-in was found by accident, and accident is not a security strategy. So the week after the cleanup went into alarms, backups that leave the building, and a restore test. Here is what watching a server actually looks like when you build it.

Cover image for “I went looking for a broken queue worker. I found a 97-day break-in.”
Strategy

I went looking for a broken queue worker. I found a 97-day break-in.

A ten-minute check on whether a queue worker was running turned into a three-month-old break-in, an internet-facing database, and four systems that were broken while looking completely fine. Here is what the investigation found, including the part I could not answer.

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Strategy

How much does custom software cost?

Every developer answers this with "it depends," which is true and useless. Here are real bands for small business projects, what moves the number, and how to read a quote when you cannot read code.

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