I was the founder of TouristEye, a travel guide app that makes trip planning really easy. We got into 500Startups, we reached 500k registered travelers and then we sold the company to Lonely Planet, the leader of the sector.

I see myself on this post. Several years ago we decided to build an amazing trip planning, that allowed you to plan your trip day-by-day. You can see some screenshots on the Chrome extension (https://chrome.google.com/webstore/detail/touristeye-planner...) (not working now). We got over 100k users using it on their trips (not daily users obviously). It was gorgeous, people really loved it, Google really loved it, but the usage was pretty low. Just 5% of our users used it.

So because we were a startup we decided to kill it and we focused on capturing user wishes, and recommending those things for their trips (kind of Google Now for trips and offline). That's what gave us more usage, more income and finally it was one of the reasons of our exit.

So, yes. Trip planning sucks as a business. But all our team remembers it proudly. It was just fucking amazing :)