90 houses, and the argument for stopping there

There is a moment, somewhere around the fourth hour of looking at hotels online, when you stop reading. You are still scrolling — the thumbnails still go past, the prices still update — but you have stopped taking anything in. I have watched this happen to my friends, planning an anniversary, a vacation, a week away they had been promising themselves for years, and I have done it myself more times than I would like to admit. Nobody designed that moment on purpose. It is simply what happens when a person with one decision to make is handed four thousand options and a set of filters.

I spent five years building the machinery that produces it. Rate feeds, mapping tables, availability caches, the ranking logic that decides which of four thousand rooms you see first. It is genuinely difficult engineering and I am still proud of most of it. But somewhere along the way I noticed that I could not remember the last time I had used any of it to book my own holiday. I asked a friend instead. She had stayed at the place. She told me which side of the building to ask for.

That is the whole of it, really. The thing that actually helps you is not a larger index. It is somebody who has been there.

What a short list is for

Kismet has 90 houses on it. It will have more — perhaps forty, perhaps eighty — and it will never have thousands, because the number is not a stage we are passing through on the way to somewhere bigger. It is the product. A list this short can be visited. Every property on it, somebody from Kismet has slept in, eaten in, and argued about afterwards. We know which rooms face the wrong way. We know which of the four Royal Suites at the Lake Palace catches the stained glass at five in the afternoon and which three do not.

You cannot know that about four thousand hotels. Nobody can. So the industry replaced knowing with sorting, and sorting is what you get: a page of near-identical rectangles ordered by a number that has more to do with commission than with whether you will enjoy yourself.

On the person at the other end

There is no chatbot here and there will not be one. When you have a question about a stay — whether the pool is heated in January, whether they can manage a birthday cake at eleven at night, whether the drive from the airport is really ninety minutes or whether that is optimistic — you will be talking to a person who has made that drive. That is slower and it costs more per booking than any software would. It is also the only version of this business worth building.

We all know the restaurant down the road that knows its regulars by heart — that starts the order before it is placed, remembers that you do not take coriander, keeps the corner table free on a Thursday. None of it is written down anywhere. Nobody has built a system for it. It works because the number of people they are paying attention to is small enough to hold in a head, and because somebody decided that paying attention was the job.

I am not romantic enough to think that scales. But it is the feeling everyone in this industry is nominally trying to reproduce, and almost all of us have been trying to reproduce it with software when the answer was always fewer rooms and more attention.

So: 90 houses. Chosen slowly, described honestly, and sold by people who have been there. If that is the wrong business, it is at least the one I would want to book through.

Chirantan Banerjee

Founder, Kismet