Travel's Biggest Investors Say No to AI Trip Planners

Two of travel's most influential investors have rejected the sector's hottest trade. Steve Case, chairman and CEO of Revolution, and Greg O'Hara, founder and senior managing director of Certares, both said no when asked whether they would invest in an AI trip planner — a category that has attracted outsized venture funding over the past two years.

Case, the co-founder of AOL, dismissed the category's durability. "It's a great service, but it's not really a durable company," he said during a session on capital allocation at the Skift Global Forum, moderated by Skift's head of research, Seth Borko.

The two investors share a contrarian thesis: AI is reshaping how travel is discovered, booked, and serviced, but the investors betting the largest sums are putting their money elsewhere. Physical assets, curated experiences, and trained human expertise are the most durable investments, they argued, because AI makes them more valuable — not obsolete.

The Case for Heavy Assets

O'Hara laid out his investment framework under a label he calls "HALO assets" — heavy asset, low obsolescence. The logic is straightforward: invest where demand is rising and supply is hard to replicate.

Certares bought into European high-speed rail on that basis. O'Hara pointed to a potential €500 billion infrastructure buildout that is expanding the market, and noted that rolling stock is harder to acquire than a Boeing 777. Scarcity, in his view, is the moat.

His wellness and longevity portfolio illustrates the same principle. It has grown to 14 companies, with revenue growing 30–35%, because "the TAM is rising and there's not enough inventory." The investment logic he described: find rising demand with constrained supply and fill it.

Curation as a Premium Business

Case is making a parallel bet through Revolution's Exclusive Collective, a platform that includes Exclusive Resorts, Inspirato, and Onefinestay. The target customer is the high-end traveler who "do[es] not want more choices."

"People want a trusted partnership with a company or a person that they really can rely on to help them navigate through this," Case said. Curation, he argued, is itself a premium offering. "People … want less decision-fatigue."

The position cuts against the industry's long-running arms race in choice and inventory breadth. Case's argument is that abundance has become a liability, and that filtering it — with human judgment — commands a price.

AI's Real Value: Amplifying Humans

O'Hara pointed to the $6.3 billion sale of Amex GBT to Long Lake as validation of a different AI thesis: the technology's highest value lies in amplifying trained humans, not replacing them.

Travel service businesses have "a lot of knowledge inside," he said, and that institutional knowledge becomes training data for better agentic tools. The practical implication for capital flows: money for AI in travel is not going exclusively to startups. It is also moving into existing service businesses that already hold the expertise and the data.

Regulatory Risk on the Horizon

Case flagged a political dimension that most travel AI strategies ignore. The 2028 presidential election will include "a referendum on AI," he said, and the politics are "moving against AI, against technology."

He noted that 10 states have already passed AI legislation. Without federal action, he warned, 50 states will write 50 different rules. Travel companies building AI strategies without accounting for regulatory risk are planning around only half the picture.

The Pattern in the Lightning Round

An informal lightning round crystallized the two investors' positioning. Both said no to an AI trip planner. Both said no to space tourism. Both said yes to members-only clubs. O'Hara said yes to an online travel agency — "if it was named Booking or Expedia."

The pattern is clear. Smart capital is flowing toward assets with scarcity and trust, and away from technology plays that are easy to replicate. For travel companies raising money or deploying it, that is the bar the biggest checks are now being written against.