Three of travel's most prominent investors are backing artificial intelligence (AI) in different ways. Certares is putting AI to work on the back office of service businesses, while Revolution is betting on it to curate luxury experiences. General Catalyst predicts AI-native owners will be rebuilding legacy businesses.
Certares has built up a large portfolio of businesses, spanning travel agencies, cruise lines, hotels and even trains. Its founder and senior managing director, Greg O’Hara, likes “service” businesses and applying AI to them.
Taking a different route is Revolution, which owns Inspirato, and has stakes in Onefinestay, biometric identity firm Clear, and other companies. Its real estate and hospitality division targets the luxury sector, with AI used to help curate better experiences for high-net-worth-individuals (HNWIs).
Then there is General Catalyst, whose chairman and managing director Kenneth Chenault argues the bigger shift is AI-native firms stepping in across multiple verticals.
Human reinforcement
Speaking at the recent Skift Global Forum in New York, O’Hara said that AI is used to make the service his businesses provide better.
“We own a lot of service businesses, and those can benefit from AI,” he said. “If I can turn a really valuable services business that has a lot of knowledge inside of it, use that knowledge for human reinforcement training and produce better agentics, that’s something I like to do. I can create that for 10 times EBITDA, not a trillion times EBITDA.”
He gave the example of a cruise agency, where an advisor has an average of 13 touchpoints with someone booking a cruise.
“We can’t always provide the most information, the best itinerary information, and AI is super good at doing that. So instead of an advisor spending 75% of their time in the back office putting this all together, we might be able to get that down to 5% or 10% of their time,” O’Hara said.
“It serves the customer better, the agent’s happier, so really boring things.”
Curated approach
For Steve Case, chairman and CEO of Revolution, luxury customers are the focus. By investing in resorts and land across Costa Rica and Hawaii, the idea is to build a portfolio that AI is not likely to disrupt, but rather enhance, according to Case.
Through Exclusive Resorts, a luxury residence club and community with 25,000 HNWIs, the bet is on leveraging AI to help curation.
“We do not want to be the place where you go for everything,” Case said. “We want to be the place to be where you get the very best of the very best. AI is helpful in terms of discovery, but ultimately people do not want more choices; there’s a paradox of abundance. People just want to be able to have a trusted partnership with a company or a person to help them navigate through this. And over time, AI will get smarter and smarter.”
The shakeout
The industry can expect to see more dealmaking. “The cycle we’re in, there’s a gold rush,” said Case, whose entrepreneurial career began in 1985 when he co-founded AOL.
“It’s a classic case: the internet, nobody knew or cared for a while, then suddenly everybody wanted to invest, and it ended up creating a boom dynamic. And we’re in that now.”
A third approach was discussed at the event during another on-stage interview by Chenault, whose investment company has nearly $50 billion in assets under management. A major investor in travel, with stakes in Airbnb and Perk, General Catalyst helped back Long Lake’s acquisition of American Express Global Business Travel (Amex GBT).
Long Lake was founded in 2023 by CEO Alex Taubin and Zach Frankel, and Chenault said this type of acquisition looks likely to continue, where AI native investment vehicles acquire legacy service businesses, like Amex GBT, as well as other companies in different sectors.
“What we loved was, they said: ‘Here are the efficiencies. But equally important, we’re interested in driving growth,’” Chenault said. “In a short period of time, they acquired 30 companies. The first company, it took six months to really get integrated from an AI perspective. By the fifth company, it was taking three or four weeks.”
For now, the three investors are placing different bets on the same technology: AI to free up advisors at Certares, AI to sharpen curation at Revolution and AI-native owners rebuilding legacy businesses through Long Lake.
Case expects it to take time to learn which will pay off: “A lot of things are getting funded, some of which will work, many of which won’t work. It will take some time to shake out.”