Douwe Osinga's Blog: Leaving Triposo

Monday, September 12, 2016

Wednesday, August 31 2016 was my last day as full time employee at Triposo, the travel guide company I started 5 years ago with my brothers and Jon Tirsen.

Triposo will continue to exist and will focus on delivering content and technology solutions for other companies. While I think that this is the best strategy for the company, it just isn't me. So Nishank Gopal will take over as CEO who has a lot more experience executing this sort of B2B strategy. I'll remain on the board and be involved as an adviser.

I'm taking some time off to think, write, code, learn and travel. With the company continuing, this isn't quite one of those Startup Post Mortems. I did want to share some thoughts on running travel companies though:

What worked and what didn't?

Triposo started out with a three pronged plan:
  • Build travel guides from targeted web crawls
  • Make the travel guides sticky by adding a travel log
  • Make money by selling tours and travel services on the go
The first prong worked rather well. We went from a few city guides that were basically mash ups of Wikipedia and Wikitravel to a travel guide that covered the world within the first year and kept improving the data quality from there on. I was especially proud when we launched the system that matched web pages automatically to our poi database and then ran opinion mining and fact extraction over those pages.

With this we could rank pois not just on one score, but on a variety of aspects - coffee, drinks, location, which in turn we could use for recommendations and personalization. On top of that we developed a nifty similarity measure for pois powering our "people that like this place, also like."

The second prong of adding a travel log, started promising. Being able to add photos and notes to entries in a travel guide and building a story that way, was fun. For us. Our users didn't use the feature very much though. They used Facebook for sharing their travel experiences. And so we were confronted with a choice: do we keep betting on two things, or do we focus on the thing that really works well, our core travel guide? We went with the last one and killed the travel log.

Sometimes I think we shouldn't have. 5 years ago, Facebook was the place to share this sort of thing, but I wonder if nowadays there would be room for a sharing platform specifically for travel. Breadtrip seems to do well in this space. But you know what they say, being too early is just as bad as being too late.

We didn't pay a lot of attention to our third prong in the first years. People spend a lot of money on travel and half of that is spent during the trip. We figured that once we had a large enough user base, they could start spending that through us. The conversion rates we got linking to web pages from our app were quite low and it seemed to us that just natifying those flows should do the trick.

It didn't. Or not enough. In our presentations we always talked about the shift from desktop to mobile and from booking before a trip to during a trip. This trend is real, but we still have a long way to go. People are happy to research a hotel on their phone, but when it is time to make a booking and enter those credit card details, they'll often quickly switch to the desktop browser, leaving your poor travel guide without its margin.

The other issue was that for tours and activities we had almost no options that had same day availability. When your model is based on telling people at the breakfast table what they should be doing that day in the city where they are, this is a problem. Again, I'm sure this will get better in the next few years, but it didn't in time for us.

What do you do when things don't work?

This is a question people in the start-up world don't talk about much. The general opinion is that when you have a start-up, you focus on that one thing that you do best. That's how you become successful, that's how Google and Facebook did it. Only when you are huge do you diversify.

That's all very well, but what if the one thing you are good at isn't enough? Initially we were doing great, our user base was growing exponentially. But that growth wasn't really viral, it was just Apple and Google sending us downloads. With the travel log shut down, we were seeing bad retention numbers. With our bookings on the go not really taking off, we didn't have a real ecommerce play either.

So what do you do? "Pivot" is a popular answer. But for every success story about pivots there are ten failures and to me it always seemed like spending the money of your investors on an idea they didn't invest in. So you start thinking about things you could add that would fix retention or fix conversion. 

City walks, mini guides, a chat room for triposo users in the location, printable posters, sponsored free wifi, audio guides, a chat bot that advises users about hotels and attractions, partly powered by a human - we built all these things and launched them. And then when the feature doesn't quite take off, you are faced with the choice of removing it and disappointing the users that enjoyed it, or have it clutter up an already complex app.

Maybe this is the right strategy. You try stuff until you hit it out of the park or run out of money. But often I think we should just have focused on building the best travel guide possible. Improve the data quality, the data coverage and the smartness. And if that's not enough, well, then there just wasn't enough a market for the original plan.

Can a travel planning app be a success?

A few month ago there was a popular blog post titled "Why you should never consider a travel planning startup." I was asked a few times about my opinion. Triposo was of course never a travel "planning" startup - we always focused on being helpful when you are on the road. But the arguments against it are very similar.

In short the article says: Getting lots of users for travel is hard, because people do it only once or twice a year. Getting people comfortable with something as complicated as a travel planning app is hard. Getting people to trust you enough to book through you rather than through an OTA they know is hard. Outbidding the site that pays you a commision for a hotel sale is hard.

This is all true and we've seen all of these things first hand at Triposo. But even though I'm writing a post about why Triposo as a consumer product hasn't taken off, I would still answer the question of whether a travel planning app can be a success with a yes.

First of all, these arguments are about all travel startups, not just the ones that do planning or help you while on the road. And yet using Kayak has become a habit. We actually succeeded in attracting a fair amount of users organically. And while we had trouble getting people to book through our app, Tripadvisor figured this out - I could read the reviews there and then go to Expedia to make my booking. And outbidding the guy who pays you a commission is the hallmark of the entire travel industry. How can outbid the hotels themselves on Google?

We focused on being a travel guide that is helpful when you are at the destination, because people don't like to plan. It seems inevitable that there will be an app that will let you have a perfect experience on your trip without you doing more planning than necessary. An app that has all the travel information in the world and knows who you are, where you are and your mood. Unfortunately it looks like it won't be Triposo.

So what's next?

I'm taking some time off to learn, write, code, read and travel. I think that when it comes to technology things have never been as interesting as they are now, so taking a bit of time to figure out what's next seems like the best approach. I'll be doing some smaller projects around stuff I want to try out. A first small one you can find here: - some scripts to import the wikipedia, wikidata and wikistats into postgres and make them searchable.

Triposo as a consumer product will continue and will remain "probably the best travel guide" in the app store. The engineering team will focus on data quality, coverage and smartness - in a way executing on the "focus on the one thing you're good at" strategy.  If you are interested in using the Triposo data and smartness for your own business, get in touch. There's some wonderful stuff there.