I have ADHD and couldn't track my money, so I built Trail

A few months ago my painter handed me back eight thousand rupees. I had overpaid him, and I had no idea. He counted it, he noticed, and he gave it back. I stood there holding the notes and thought: this man is managing my money better than I am.

I am a full-time software engineer. Decent paychecks. And I still could not have told you where the month went. That was the day I stopped pretending it was a phase.

We make good money. Where does it go?

It is the question at our dinner table every month, and I know it is the question at a lot of tables. It is never the big stuff. Rent does not hide. The mortgage does not sneak up on you. It is two hundred here, five hundred there. Cash, two bank accounts, a micro-bank, my wife's card, an SMS alert that buzzes and is forgotten by the time I lock the phone. None of it gets logged. The month just evaporates, and next month the same table asks the same question.

I live outside the US, where almost nothing logs itself. There is no clean feed of every transaction. Half of what I spend is cash. The apps that assume a tidy card statement have never met my actual life.

Every app wanted me to be someone else

I tried them. All of them. And every one of them wanted a twenty-minute setup: categories, budgets, link your bank, build the perfect envelope system. They were designed for a patient, disciplined, executive-function person who sits down on a Sunday and reconciles.

I have ADHD. That person is not me. I would open the app, feel the weight of the setup, freeze, close it, and never open it again. That is not a character flaw I can budget my way out of. It is how my brain works. The apps read my abandonment as laziness. It was never laziness. It was friction, and friction is a design choice.

The first time you log something is the work. The next hundred times should be free.

The rule I built the whole thing around

So I stopped looking for an app that would fix me and built one that meets me where I am. The entire product sits on one rule: the first time you log something is the work; the next hundred times should be free.

Here is what that means in practice. The first time I log my evening tea, I tell Trail the amount, and it learns everything around it: which account it usually comes from, which folder it belongs in, what to call it. The second time, and every time after, Trail has already made those calls. I just confirm. This is the part I care about most, and it is the thing generic scanners do not do. They read a receipt. They do not remember what you did with it. Trail learns your routing from your own past activity, so repeat expenses file themselves. That is the whole reason I can use my own app.

It also means I stopped needing discipline. The renovation that buried me in cash receipts, the trip where I finally knew what every ringgit cost: those are their own stories. But they both run on this one rule. Log it once. Let the app do the next hundred.

What Trail actually is

Trail scans, files, and finds receipts. You capture a spend however is easiest in the moment: a photo, a share from an email or PDF, a typed line, or a voice note to Siri from the back of a cab. It all lands in one structured, searchable log. Later you can ask it plain questions about your own spending and get a real answer.

What Trail is not is a coach. It will never send you a notification about overspending on coffee. It does not budget-police you or guilt-trip you. It is a memory, not a nag. It remembers where your money went so that you can find it. It does not have an opinion about it. I did not want a coach. I wanted a memory.

Launching now

As I write this, Trail is with Apple in App Review, and it is launching soon on iOS and Android. The free plan is fifty logs and fifty Trail AI questions, a one-time allowance, no card required and no trial that quietly turns into a charge. If it earns a place in your week, Pro is $4.99 a month or $47.99 a year. That is the whole offer, stated plainly, because dark patterns are just another kind of friction and I am tired of friction.

I built this alone, with AI doing a lot of the plumbing and none of the product decisions. I built it because a painter counting my change was a better system than anything I owned. Now the system is an app, and it keeps the trail for me. Following along as I ship it.