Can trip planning startups ever succeed?

The trip planner pitch has been around for a while now. It starts with “Travel is broken, the average consumer has to use 36 websites to plan a trip.”

The solution is to create a super-platform to do all travel research, bookings, sharing and management in one place.

The go-to-market strategy used to be content marketing and SEO, but now involves mostly peer-to-peer sharing and influencers on social networks.

But up to now, trip planners have always failed.

There were many problems with the proposed solution:

• Content. Gathering and organizing the information required makes it really difficult and expensive to build. You need breadth and depth of global destination content, and it needs to be current, and wherever relevant, it needs to be bookable.
• Users and loyalty. Once you’ve built it, how are you going to find users? And assuming you have the answer to this, how are you going to keep them so you don’t have to pay Google each time? Lack of frequency of travel for the vast majority of humans is the enemy here, as it is for almost every travel company on the planet.
• Product. Does your product work? Can you overcome the learning curve for new users? Consumers are pretty comfortable with Google, and the major online travel agencies mostly have an excellent user experience and aren’t really broken, at least when it comes to flights and hotels. 
• Revenue. Assuming it works, and users keep coming back, can you monetize that traffic? Trip-planners are normally positioned at the top of the funnel, before transactions are happening.

It’s different this time

• Content. With the launch of ChatGPT in 2022, the barriers to entry here were eliminated. Any generative artificial intelligence-connected website now has access to the world’s travel content. With little development, that content can be triangulated with sources like Google Places, to make sure it’s current and relevant. You could even argue that when it comes to content, the largest travel companies in the world have lost 100% of their previous advantage. This content is also searchable without the need for complex algorithms or categorization. 
• Users. There’s a much bigger target market of consumers comfortable transacting online these days. But the size of the market was never the key factor, and aside from that, nothing has really changed here. When it comes to retention, there’s certainly more willingness to use apps these days, but you still need to get people to your app in the first place. Gamification is easier to create in modern tech platforms, which could be one of the solutions. Ultimately though, the problem is as large as it ever was.
• Product. When it comes to development, everything is easier and more accessible now. Easy and inexpensive cloud hosting, access to better application programming interfaces (APIs) on both the content side and the bookings side, and just better tools all around to improve efficiency and the final product. Personalization can also be done now, and without the need for any previous customer booking data. This allows personalization that actually works, which has never happened before in travel. Many argue that a lot of consumers enjoy planning the trip, which is the reason these tools aren’t needed. Surely, the right solution would solve that by replicating that enjoyment within the platform itself.
• Revenue. You could argue that if you solve all of the above, then this part will eventually fix itself. A good, sticky product should be able to convert enough customers to create viability, at least at the hotel stage or experiences stage. The pressure here is less than it was because the price to build the solution is a fraction of what it was a few years ago.

The problem is that you could argue that any one of these factors acts as a super-veto on the success of all trip-planning startups. You have to solve ALL of them to avoid failure.

It also might come down to a matter of definition. What makes a trip-planning tool different to a travel research website with a couple of tools bolted on? That's a question that will probably allow most people to claim they were on the correct side of this debate.

If I was a betting person, I would first say that Gemini, together with Google Travel and Maps, will become the first successful trip planning product. When it comes to startups, I’m still on the fence.

In the very near future, you’ll probably see the best trip-planning tool created to date. So if somebody builds the ultimate tool, which actually works, has access to all the world’s travel information, and has all of the bells and whistles that one could hope for, does that mean people will actually use it, which will lead to success?

My best guess is … maybe.