Why can’t I book a hotel room tonight?

This was the problem HotelTonight founders Jared, Sam & Chris set out to solve

Why can’t I book a hotel room tonight?

“For the amount of money that we’ve spent on marketing, it’s obscene how many people are using HotelTonight,” laughs Jared Simon, who started his career in corporate finance prior to realising “life was supposed to be enjoyable”. And with 13 million worldwide downloads of the last-minute hotel-booking app, we’re inclined to agree.

Travel is such a fun industry because it’s generally an early adopter of new technology. And it’s a driver of that technology. I would argue that when the Internet started coming into being in the late ’90s, the travel industry was one of the first industries to jump in with both feet and really embrace this new technology, and push it along and demonstrate the value – the utility – of the web for booking travel. This shift to mobile is every bit as dramatic in my mind as that shift to the web was, and the travel industry is going to embrace this one as well.

These kinds of ideas are like a gas. They’ll expand to fill whatever space you give them. So we forced ourselves. We started working on it in September 2010 and we said we’re going to submit this to the app store by Christmas – that’s 10 weeks, and it’s just three of us, and we did it… The product wasn’t nearly as slick as it is now. The app looked really beautiful, but behind-the-scenes it was me calling hotels. It was very low-tech in the background. We iterated – built that function up over time, and now the back end is just as slick as the front end is.

It was 11pm on a Tuesday night… when we got the email from Apple saying we were live. I won’t repeat what we said, but we had to get some hotels on board. They don’t all move as quickly as we want them to move, so we ended up having a few up there that didn’t necessarily know that they were up there… But, you know, you do what you have to do. You’ve gotta be scrappy at the beginning, and it worked out great; and we quickly backfilled with the real partners and everything worked out fine.

Most people didn’t have smartphones at that point. And we didn’t have an app to show them even if they did have a smartphone – but the vision resonated with hotels. Hotels have long been looking for some sort of innovation in the industry that gives them a safe way to dispose of distressed inventory. These are rooms that they know are going to go empty, they would like to get rid of them at an aggressive price, but they don’t want to aggravate their loyal bookers who might have paid full price. So our solution was a novel one; the solution being, ‘hey, we’re only going to show a few hotels each day and then we’re going to rotate them every day so that no one can predict which hotels are going to be on display on any given day.’

Getting your name out there is difficult. The biggest challenge by far in travel is… getting the attention of your potential customers. It’s maybe even more difficult when you tie two hands behind your back and say, ‘I’m going to be mobile only and I’m going to forgo all these other media we can use – a website, things that everyone’s relied on for years. We’re going to make a bet. We’re saying the world is moving to mobile, we’re going to be there NOW and focus on it NOW so we can be the best in the world.’

We do a lot of creative things behind the scenes – whatever we’ve got to do to make sure that we can stand by our promise that you can count on HotelTonight. So sometimes we’ll pre-book the rooms – we take the risk on those rooms at that point. Generally, the most successful thing we do is make it worth the hotel’s while to wait and hold that room for our guest. Part of the reason for that is our guests are generally the kinds of guests that hotels want to stay in their hotels.

Choose a problem to solve that is a real problem. Don’t be a solution in search of a problem. And choose something that is universal – a fundamental challenge or pain point for people all over the place, like finding a place to stay tonight. And go in with gusto and conviction. Don’t hedge. You’ve gotta bet on it and try it, otherwise if you fail, you’ll never know if you failed just because you didn’t commit or if it wasn’t a good idea. But if you commit to it, you’ll know for sure. And you know what? It’s likely you’ll succeed.


This is an excerpt from Issue 24 of The Collective.