Steve Case spent the better part of two decades getting America online. Now the AOL co-founder is making a bet that sounds almost like heresy from a tech founder: The more artificial intelligence floods into travel, the more its wealthiest customers will pay for a human being they trust.
He has already acted on it. In April, Onefinestay — the luxury rental brand within Case’s Exclusive Collective — handed roughly 200 London and Paris homes to management partner Veeve and pared its London collection to about 40 of its best, part of a pivot toward larger homes in the leisure destinations where its guests actually want to go. Case frames the cuts as a question of standards.
“For us — and us meaning the Exclusive Collective, which includes obviously [Onefinestay], but also Exclusive Resorts and [Inspirato] — it’s really a decision that quality trumps quantity,” he said.
The old portfolio offered plenty of variety, and in his telling, the variety was precisely the problem.
“Some were really great, and some not so great,” Case said. “It created work for the customer. They had to self-curate.”
The new screening test is personal for Case, who is chairman and CEO of investment firm Revolution, whose real estate and hospitality arm, Revolution Places, spans Exclusive Resorts and the Punta Cacique development in Costa Rica. Case controls the Exclusive Collective.
“I want to have things in the Exclusive Collective that I’d be happy taking my family to,” Case said. “In some ways, consistency is the new luxury.”
Case hired Melissa Xides to run Exclusive Resorts, the Collective’s flagship club, earlier this year. Xides spent seven years as Bergdorf Goodman’s chief retail officer, and she arrived carrying a statistic that stuck with Case during the interview process: Most of what Bergdorf sells goes out through its personal shoppers, shipped to customers sight unseen. The lesson extends well past handbags.
“These high-end luxury customers... are not going into the store, are not searching on e-commerce sites or using AI or other things to find things,” he said. “They’re relying on a person that they’ve learned to trust, because they have a sense of their style and preferences and [needs] and wants.”
Luxury retail worked that out years ago. Luxury travel, he argues, is midway through the same realization, and the people best positioned to profit from it already have the client list. If you sell luxury travel for a living, the person at the center of that realization is you.
Look inside Case’s own ecosystem, where the digital booking paths are as sharp as any in the industry, and even there, the humans keep winning.
“Even though we have excellent digital platforms for our brands, and some do book completely online, the majority of people rely on their advisors, and that’s true with all the brands,” he said.
The deeper the trust runs, the more of the decision gets handed over.
“When they[’ve] built up that trust, they’ll say, ‘Where should I go?’” Case added.
He counts three versions of that trusted advisor figure.
“People are looking for that trusted advisor, whether that advisor is a full-time travel advisor... whether that is somebody who’s working for a club like [Exclusive Resorts], or whether that be a member who is talking to other members,” he said.
He watched the third kind at work on an Exclusive Resorts trip to Japan late last year, where some 20 members spent their evenings trading recommendations. (“You really haven’t gone to the house in Tuscany? You should go to the house in Tuscany.” Consider us filled with Italian vacation real estate envy.)
None of that, he argues, can be outsourced to a review feed.
“There is no question — I’ve heard this directly from some of the leading platform companies — that there is more... fraud, if you will... where AI is sometimes being used to [create] fake reviews,” Case said.
His larger conviction runs against most of Silicon Valley’s: “I think in this digital world the hunger for a human touch will grow, not decline, in the years to come.”
Once again, the tales of tech-fueled death to the travel advisor sector have been greatly exaggerated.
“Partnering with luxury travel advisors, we think, is hugely important,” Case said. “They have a lot of credibility, they have broad history, they have expertise in certain things that clients will be looking for. We don’t view it as competition, we view it as a way to better serve their customers in a way that is win-win-win for all.”
The ecosystem Case keeps returning to spans three brands, each a different path into the same philosophy. Exclusive Resorts operates as a private, referral-based membership club; Inspirato as a flexible luxury travel subscription club; Onefinestay as a straightforward luxury rental brand, no membership or subscription required. Together the three serve more than 25,000 high-net-worth travelers annually, and there’s plenty of runway to grow given soaring wealth accumulation globally.
The growth plan leans on partnerships as much as portfolio.
“A big, big focus the next year or two is [to] expand the tapestry of alliances we have,” Case said.
The template is Exclusive Resorts’ arrangement with Rosewood Hotels & Resorts, which has expanded over the past couple of years; Case said Rosewood is pleased with the results.
Next on the map: two new Onefinestay flagship destinations planned before the end of 2026 — one in the U.S. and one in Europe, a company spokesperson said, both in markets where the Collective already has a presence. Case’s thinking on why that presence matters is on full display when he talks about Costa Rica, where he has been invested for two decades, including the opening of Waldorf Astoria Costa Rica Punta Cacique.
“[Inspirato] has homes in Costa Rica, Exclusive Resorts has homes in Costa Rica, [Onefinestay] has homes in Costa Rica,” he said. “Separately, we have a peninsula we’re building out in Costa Rica, so there’s a critical mass in a market like Costa Rica that makes it... logical to have that be more of a priority.”
For all the bullishness, Case is willing to say what few luxury operators will: the segment overreached on price.
“I do think some got a little ahead of their skis on pricing coming out of the COVID revenge-travel [era],” he said. “There was a little bit of sticker shock, even in the luxury segment. I think people have had to moderate their expectations a little bit.”
“Wealthy people are also value conscious,” he added. “They don’t want to be taken advantage of, and they don’t want to feel like they... paid a really high price and then saw a lower price somewhere else.”
But the demand side keeps him optimistic. Between an IPO pipeline minting new fortunes and the intergenerational wealth transfer already underway, he sees the market widening rather than thinning.
“There’ll be [thousands], maybe tens of thousands of people that come into a fair amount of wealth,” he said.
Given the surge of potential new customers, one can’t help but think other tech titans are watching this space. Ask Case the yes-or-no question — is there still transformational disruption coming to this market? — and he is certain there will be.
“Absolutely, absolutely,” he said. “I think there’s still a lot of things that are going to happen in the next 10 or 20 years, which makes it exciting.”
But any kind of disruption can’t ignore the real luxury these clients crave most: time.
“If [they] only have a couple of weeks a year to [travel] with their family, it better be right, it better be great,” Case said. “Ultimately, it’s what are the experiences you’ve built around it that really does create that bond, that connection... They’re not really looking for a place to stay, they’re looking for a place to connect or reconnect with [their] loved one[s].”
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