Dear TripIt: I Rewrote You in an Hour on Holiday in Phnom Penh

Dear TripIt,

We need to talk. I am writing this from a hotel balcony in Phnom Penh, on holiday, at an hour when nobody should be making decisions about their relationships. And yet here we are.

The good years

We had something special. Nineteen years. 706 bookings. You were there for every red-eye, every delayed connection in Doha, every hotel I swore I would never stay at again. Seattle to Long Beach on Alaska in 2007. Manila to Saigon on Cebu Pacific in 2013. Melbourne last month.

And every year, I paid you. Forty-nine dollars. I thought you were the one.

Then I looked under the hood

This week I have been building a private database for my whole life. Travel was one of the ten areas. So, on holiday, I sat down to figure out what a travel app actually is.

And TripIt, I am sorry, but you are a database. And a little script that reads my Gmail. That is it. That is the whole relationship.

It is not you. It is... actually, no. It is you.

So I built my own

Here is the entire rebound:

I loaded twenty years of confirmations into it. It came back with 172 trips, 250 flights, 16 countries and 969 nights away, all the way back to April 2007. With a map, an upcoming-trip view for airports, and an inbox for the bookings it is not sure about, because a database that guesses is worse than one that asks.

Full honesty, since this is a breakup letter: the travel part took about an hour. The whole private system around it took the afternoon, built the way I tell founders to work with AI. Plan first, then multi-delegate. The plan did the heavy lifting. The agents did the typing.

The settlement

I took back my forty-nine dollars. Refund status: approved, by me.

This is not really about TripIt. It is about how many apps we pay every year for what is, underneath, a table and a script. Once you can see that, you start looking at your whole subscription list differently.

If you want to break up with an app or two of your own, the whole plan is here. Or book a discovery call and I will show you how it works. Bring tissues.

Dave.

Things people ask me about this

Can you really replace TripIt with your own app?

For personal use, yes. A travel tracker is a database of bookings plus something that reads your confirmation emails. With Claude doing the reading, the hard part is deciding what a trip is, not writing the code.

How does it get trips out of Gmail?

A small Google Apps Script runs inside the Gmail account every hour, finds booking confirmations, and sends them to the app. Claude extracts the flights and hotels, and anything uncertain goes to an inbox for approval instead of being guessed.

Will you share the code?

That is the plan: an open source version for people who want to run their own, and a small hosted version for people who do not.