Why real-time entry fails, and what it took to fix it

By Paul · practicing attorney, Colorado · founder of OnPoint

I have been bad at contemporaneous time entry my whole career. As an associate, I typically reconstructed weeks — sometimes a month — from emails and a calendar during the last couple of days of the month, knowing full well I was leaving real work unbilled because I could not remember it. Years later, running my own practice, nothing had changed except that the unbilled time was now coming out of my own pocket.

Every knowledgeable attorney says the same thing: enter your time daily. Everyone agrees. Few actually do it.

So I built a tool where every design decision answers one question: what is still keeping the cost of one entry above that attention threshold? Here is what that took, point by point, because I think the reasoning is useful whether or not you ever look at my app.

1. It has to be a place you do not mind being

This sounds like vanity and it is not. A capture tool gets opened ten or fifteen times a day at not-so-great moments, right when you are tired of the work you just finished. If it looks like enterprise billing software, many people will not open it.

I spent an unreasonable share of the build on how the app looks and how few taps anything takes, because intuitive design matters and has been sorely lacking in this field. Tap a client, tap the hours, save. The prettiness is retention mechanics, not decoration.

2. Typing is the wrong input at the moment of capture

At the end of a call your patience is gone, but you can still talk. So you dictate the whole entry in one breath: “Johnson, one point seven, consultation re settlement agreement.”

The speech recognition runs through the phone’s own engine, and then AI structures what you said into the entry: client, hours, matter, narrative, each in its place. Nothing saves without your approval. Eight seconds of speaking while the call is still fresh beats twenty minutes of reconstruction when it is not.

3. The cleanup cost has to go to zero too

Notes captured in the moment read like notes: “talked to opposing counsel about the fence line.” That is fine, because there is a Polish function that rewrites rough words into clean billing language — in this case, “Conference with opposing counsel re boundary dispute.” It shows you your words and the rewrite side by side, and you accept it or keep yours.

The strict rule I built into it: it rephrases, it never invents. It cannot add work you did not describe, because an embellishing polish function in billing software is a bar complaint waiting to happen.

Polish came from the associate meetings a partner at my old firm used to run. Every month she gathered the associates in the board room and read out the worst-worded time entries we had filed. At the time I thought: wouldn’t it be great if software just cleaned every entry up to billing standards? Now it does.

4. The entries you never captured at all

The genuinely lost money is the call you took in the car and the meeting that never got written up. So the app connects to your Microsoft 365 account and suggests entries from your own calendar and mail: the day’s meetings arrive as drafted time entries, and the day’s correspondence clusters by client, ready to save or dismiss.

It reads subjects and participants on your device, never message bodies, and it is off until you turn it on. This is the feature that catches what even a good capture habit misses.

5. The price has to be an easy yes

It is $9.99 a month, or $99 a year, with a 7-day free trial. That number is deliberate: associates and solos pay for their own tools, and a capture tool you hesitate over is a capture tool you cancel. At about ten dollars it needs to recover roughly two minutes of billed time a month to pay for itself.

On privacy, because it deserves an answer

Your entries live on your device and sync only to your own account if you sign in. The AI receives only the words you typed or dictated, plus your client and matter names. Audio never reaches my servers. Billing data is a map of your practice, and I built the tool as if I would have to explain that map’s location to a client.

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