Jason Calacanis and Brad Gerstner on How AI Is Changing Travel

The travel industry could see a disruption from generative AI sooner rather than later.

That was the consensus during a discussion with tech investors Jason Calacanis and Brad Gerstner on Wednesday evening at the Skift Global Forum in New York City. Moderated by Skift CEO Rafat Ali, the session was a look at the future of travel as AI reshapes the world. 

Jason Calacanis, a tech entrepreneur and investor, is the author of the book "Angel" and hosts two podcasts: This Week in Startups and All-In.

Brad Gerstner, is the founder and CEO of Altimeter, a tech investment firm based in Silicon Valley. He says he has participated in more than 100 initial public offerings.

Below are four of the biggest travel-related takeaways from the discussion.

Travel Search is Stuck in the Past

“We're trying to figure out the perfect hotel room, the perfect flight, the perfect car, the perfect sunset view, the perfect restaurant — and Google's pretty unfulfilling in that regard. But it was a hell of a lot better than the world before we had access to anything, and so it felt automagical."

"But here we are 20 years later, and we still experience the world in roughly the same way. And as much as I love all the [online travel agencies], they're effectively search engines in the underbelly of Google. So you have a search engine — this is a card catalog that leads you to another card catalog and a page filled with advertising."

"I really look forward to the experience when I just say to my general purpose AI — who already knows everything about me, knows where I like to stay in New York, knows the restaurant, knows the view, knows the table — I just say, ‘Hey, next Thursday, book me the standard.’ And it happens.” 

- Brad Gerstner

Who Will Be the Big Winners?

“I think there is an open question right now. Does the unique data and talent and skills of Booking.com and Expedia and Kayak, of TripAdvisor, etc. — does that entitle them to an advantage in this new thing? Or, as Clayton Christensen and others will talk about the classic 'innovator’s dilemma:' Does your economic business model and the talents and treasure you have inhibit your ability to reinvent yourself?

Google right now is a monopoly with monopoly profits. So whatever the thing is in the future that the world is going to become — I would argue it's unlikely that it will be as good for them as it is today. It's very difficult for monopolies to survive disruption.”

- Brad Gerstner

How Travel Booking Will Look

Regarding Google’s recent addition of travel booking capabilities in Bard:

“You'll be able to ask very interesting questions: ‘Hey, I want to go surfing.’ Or, ‘I want to go snowboarding. I want to do it in deep powder. What are my choices? And can I get a business class ticket there? And I want to do it for under $10,000.’ What you would describe to a travel agent: That’s coming back. That's what the interface is going to be, and it's going to work. Right now, it doesn’t work. 

"Twelve months from now, I guarantee you will be able to say, 'Book me three Michelin star restaurants when I'm in Hong Kong. Book me a flight in business class; I want a sleeper seat with the best wifi. And I want to go for a week. I don't care what days I leave.' In one year, that entire agenda will be done for you.”

- Jason Calacanis

Regarding Meta’s announcement Wednesday that it’s adding an AI chatbot to live within WhatsApp:

“You're not going to type anything in there. You're just going to say to your Meta AI, 'Book me the Air India flight next Tuesday at 9 a.m.' And it's going to do it. It has all your payment information as a direct API to Air India; it has everything it needs to know. We've been talking about this for 20 years.” 

- Brad Gerstner

The Effect of AI on the Workforce in Travel and Beyond

“Entire job categories are being made 30% more efficient, 20% more efficient, 50% more efficient in year one. And I think in year two, it speeds up. What's getting hit right now: event planners, travel agents, a  lot of repeatable stuff … Anything that's being business-process-outsourced will be done by AI."

- Jason Calacanis