A while back I told you I was building a mileage tracker. I didn't build one. The tracker I ended up with is a free one somebody else already made, plus a small piece I built around it.
This post is the process, so you can run it on the next thing somebody tries to sell you. The short version is one habit: before you pay for software, or pay somebody to build it, open whatever AI chat you already have and tell it to argue against you. Not help you. Argue.
I drive for work: shoots, client meetings, and route days for a vending business I help run with my family. Every one of those miles is a deduction if you can prove it, and the IRS wants proof: the date, how far, where you went, why, and which business it was for. No log, no deduction.
My version is messier. I have two businesses, so every trip has to land in the right set of books. The vending business has a second driver who uses his own vehicle. And my QuickBooks subscription runs out in mid-October and I'm not renewing it. I already moved my books into a free program that lives on my own computer. So I needed miles to flow into those books without me remembering to open an app every time I got in the van.
I use a process I built with Claude called Forge. Before the AI writes anything, it has to research, write down what would make the project fail, and try to kill the idea. My first ask was huge: an app that replaces QuickBooks and tracks my mileage automatically. That is basically "build me a small software company."
It didn't start building. It asked: what would make you regret this in six months? That's the question to steal. I gave it three answers:
I wrote those down before any research, so when I got excited later, the bar couldn't move.
The AI looked at what already exists and said don't build this, buy one. It recommended TripLog, which has a free plan, with a paid plan at $4.99 a month. It also noted that tracking drives on a phone is genuinely hard, and the good apps have spent years tuning it.
For most of you, that's the right answer. One business, one car, you just need a log: get the free plan and be done in 10 minutes.
I didn't take it. It isn't the $5. It's that everything is $5. Five here, 14 there, QuickBooks on top, every month, forever, and you don't own any of it. Your data lives on their servers. What I'm really building toward is a small business that owns its own back office, on its own computer, with no monthly bill. The mileage app was just the first piece.
A good process doesn't say "okay boss" when you override it. It went harder. It set up six separate AI reviews, each attacking a different part of the plan. Nineteen attacks, and six of them were kills, meaning the plan fails unless you fix it. In plain English:
It looked again and found Otograph, a free open source mileage tracker. Open source means the code is public and anyone can run it on their own computer for free. It works with a free phone app called OwnTracks (iPhone and Android) that sends your location to your own computer. Otograph turns that into trips, business or personal, with purpose, vehicle, and an exportable IRS deduction report. It uses the iPhone's own low-power location wake-ups, the ones Apple built for exactly this.
The person who made it is on GitHub, and I want to say thank you, because they did the hard part. Search "Otograph" on GitHub to find the project and give it a star. When I found it, it had two stars. If this post sends a few people their way, great.
It isn't perfect for me, and its own documentation says so: one person per install, no idea I have two businesses, tested on Linux. None of that was a reason to build my own. Here's how the process scored my options:
| Option | Score |
|---|---|
| Build my own tracker | 3 out of 10 |
| Build only the small piece that's missing | 7 out of 10 |
| Build the small piece and tell the story, so other owners can do this | 9 out of 10 |
Think of a bookkeeper between two desks: one holds the trips, the other holds my books, and the bridge carries the paper across. It sorts each trip into the right business, figures the deduction at the current IRS business mileage rate, and writes it into the right books. Anything it isn't sure about, a gap in tracking or an unlabeled trip, it sets aside for a person to look at. It doesn't guess.
I built it test first, on fake trips. The project has a wall for real data: a check that refuses to run if real data is in the wrong folder, and another that scans before anything gets saved. Careful is a habit. A lock is a lock.
Then I put Otograph on my home server with signups off and a nightly backup, and tested a restore, because a backup you've never restored is a guess.
What broke: getting my iPhone to talk to it took longer than building the bridge. OwnTracks can load settings from a QR code, a link, or a file, and all three failed on my iPhone. What worked was typing the settings by hand and pasting the long password from my Mac. My second driver's Android sent his location every two seconds and drained 58% of his battery in 8 hours. One setting fixed it. These were setup problems, not tracking problems.
The bridge isn't released yet. The code is private for now.
If you want this set up in your business and don't want to fight the setup, comment with what kind of business you run.
Next, I let AI read a small business's spreadsheets and it found mistakes that had been sitting there for months: Claude Found the Excel Mistake That Overbilled a Customer.
I send what I'm building, what worked, and what broke. Free, no fluff.
Free. Unsubscribe anytime.I'm a marketer who builds his own tools. More at adamgarceau.com.