I have known Brian Harniman, the Head of Strategy at digital transformation agency From since the early days of Skift — he was amongst the first online travel veterans to latch on to the potential of what we were building. Harniman is a serial entrepreneur with over 25 years experience leading innovation in travel companies. He was on the founding team of Priceline.com and held executive positions at Kayak, Hickory Global Partners, Open List, Where I’ve Been, and more. He and I have talked about travel startups informally on and off for years.
This current episode’s context was sparked by a LinkedIn post I did a few weeks ago about travel startups in an age of artificial intelligence: “We are in the travel planning/inspiration/recommendations startups circa 2015 phase of AI boom now… dozens & dozens of them launched in the social media boom phase, all fizzled out because… no way to get enough usage frequency, and then drive to actual transaction which is where you make all money in travel…. I also won’t dump on any specific startups/single-feature companies that have launched, too early to write off all the innovation to come, but as with every wave 8/10 will fizzle out, one will get bought by a larger player & maybe one becomes next the next Airbnb. But even then…it will have to be all around transaction, that is where it is at in travel, nowhere else.”
And Brian responded to any post with this: “Planning startups don’t connect well with booking sites – the outdated content and pricing kills demand or worse, creates anger with failed bookers. Content/recommendation startups don’t scale without spidering or autogenerating content, and that ruins their cred with users who are looking for “real” reviews and ratings. And yet, every travel startup competition has a company that is going to solve this problem for us.”
Which was enticing enough to invite him on to The Skift Travel Podcast and discuss this more in depth. And so it was, amongst the most fascinating conversations I have had on travel startups in a long time and definitely worth your time to listen in. 
Some of the points we discussed:

How a travel startup’s position in the transaction funnel corresponds directly to its survival. 

How generative AI like ChatGPT is currently being deployed in travel booking.

In this age of AI, if planning does come into the booking process, what happens next? Can the travel planning phase be shortened?

The travel search box is broken. ChatGPT could be really instrumental in streamlining that down, what are the possibilities?

Travel booking filters and why they are evidence of travel search being broken.

Most travel companies don’t have a unique enough corpus of content for training data for AI.