Revolution’s Steve Case on Which Friction to Protect From AI

The company behind Exclusive Resorts, Inspirato, and a Costa Rican peninsula invests by asking what AI can’t replicate. That’s the through-line for Steve Case, the AOL co-founder turned Revolution chairman and CEO, who joins Skift Global Forum on September 22–24, 2026, to lay out the rule behind those bets and why he thinks the most important design decision in travel is which friction to protect.

The Rule He Decides By

Skift: The pace of change is only increasing. When you’re trying to make a decision, what’s the actual test or rule you use?

Case: I start with a simple question: Will AI make this more abundant, or will it remain scarce?

That’s the idea behind what I’ve been calling the Scarcity Shift. Throughout history, technology has made certain things cheaper, faster, and more accessible. AI is accelerating that trend, creating unprecedented abundance in the digital world — information, content, planning, routine tasks. As those things become abundant, the things AI can’t create become more valuable.

That test has shaped real decisions for us. When we committed to developing Punta Cacique, an oceanfront peninsula on Costa Rica’s Guanacaste coast, the question wasn’t whether AI would change hospitality — it will, in dozens of useful ways. The question was whether anything could ever create another peninsula like that one. It can’t. The same logic runs through our land holdings in Hawaii and our membership businesses: AI can help operate a business more efficiently, but it can’t manufacture an irreplaceable place, build decades of trust with a community, or replace the feeling of being somewhere truly special.

So the rule is simple: use AI aggressively on everything that’s becoming abundant, and invest your capital in everything that isn’t. And recognize that in an increasingly digital world, people will hunger for real community with real people in real places.

Skift: The customer journey keeps getting longer and more fragmented. How has your thinking changed about traveler choice and how your company curates products and offerings?

Case: People have access to more information than ever, yet they often feel less certain about their decisions. That’s the paradox of abundance: more choice doesn’t create confidence, it creates decision fatigue.

You can see it in the data. Travel advisors — who many predicted the Internet would kill — are thriving, and the growth is coming from the generation everyone assumed would never use them. In a recent Chase Travel survey of more than 4,000 travelers, 60 percent of Gen Z and Millennials said they want to use a travel advisor. The most digitally fluent generation in history is choosing human judgment. They may be influenced by social media, and use AI for discovery, but when it comes to making a choice – to commit not just their money, but also their time – the digital generation values the recommendations of real people.

That tells you where AI fits. It’s remarkably good at logistics, research, personalization, and administrative tasks, and that’s exactly where it should be used. But the more AI handles the mechanics, the more valuable editing and curation becomes. People don’t want infinite options to choose from — they want somebody they trust to narrow the options, so they can travel with confidence. We’ve seen this with Exclusive Resorts. Our members trust in our properties and in the curation of experiences and amenities our team curates for them and their families. In an age of infinite choice, curation isn’t a feature of the product. Increasingly, it is the product.

Relationships That Compound

Skift: How are you thinking about how the traveler/customer relationship has evolved, and what companies need to do to maintain it?

Case: The biggest evolution is that the relationship used to be transactional and episodic — you book, you stay, you leave, and the next trip starts from zero. The companies winning now are building relationships that compound instead of reset.

That’s why we’ve leaned into membership and club models across our portfolio. When I invested in Exclusive Resorts more than two decades ago, I thought it was mostly about the homes. Over the years I’ve come to learn that the homes are table stakes. What people really value is the community — being part of a club of other interesting people, and being able to make new connections and create new friendships while they travel the world, staying in awesome, well-curated, well-managed residences along the way. By the tenth trip, we’re not selling members a vacation — we know how they celebrate milestones, which properties their kids grew up in, what they’ll want before they ask. No algorithm starts with that head start, and no competitor can copy it, because it’s built one stay at a time.

That’s also why we more recently acquired Inspirato and onefinestay. They extend the platform and enable us — now known as The Exclusive Collective — to serve a wider range of needs for an ever-expanding group of families, all seeking to travel with confidence and live their best life.

The mechanics of loyalty haven’t changed: people remember how you made them feel — whether someone anticipated their needs, solved a problem before it became one, or helped them discover something they wouldn’t have found on their own. What’s changed is the stakes. In a world with more choices than ever, trust is the deciding factor, and trust only compounds inside a relationship. The best hospitality companies have always understood they’re not selling rooms; they’re building relationships that get more valuable with every trip.

Which Friction to Protect

Skift: What is one area that the travel industry doesn’t discuss or pay attention to enough?

Case: The difference between good friction and bad friction.

Bad friction is waiting in long security lines, sitting on hold with an airline, sorting through infinite options, dealing with confusing logistics. AI can eliminate a lot of that, and it should — that’s a real opportunity.

But good friction is something entirely different. It’s taking a wrong turn and finding a neighborhood you hadn’t planned to explore, trying a dish you’ve never heard of, learning a few words of another language, or having an unexpected conversation with someone who lives there. Those moments require curiosity, vulnerability, and a little uncertainty, but they’re the experiences people remember most. This serendipity value guides our efforts in Punta Cacique, as we’re learning from what people love so much about Hawaii – staying a great resort, but using that as a base camp to explore the off-the-beaten-path stops that make the vacation memorable and lure you to return again and again.

Here’s the risk: as AI gets better at optimizing every trip, we could accidentally sand away the serendipity people are actually paying for. The most important design question facing this industry over the next decade isn’t which friction to eliminate — AI will handle that. It’s which friction to protect. And how to use technology to do what it does best, but always remember that hospitality is a people business. Just because you can automate something doesn’t mean you should.

Where This Conversation Lands

• The Scarcity Shift as a capital rule: put AI on the abundant, capital on the scarce. It’s a clean test, but it asks what counts as truly irreplaceable, and whether “invest in the scarce” is a strategy any operator can run or one reserved for those who can buy a peninsula.
• Friction worth protecting: Case argues the decade’s real design question is which friction to keep, not which to cut. For operators whose entire roadmap is friction removal, deciding to preserve some on purpose cuts against the reflex.
• Curation as the product: he backs it with data: 60 percent of Gen Z and Millennials want a travel advisor. If curation is the product now, that reframes what a hospitality brand actually sells, and where the margin sits.
• Relationships that compound: the membership model’s edge is a head start no algorithm has and no rival can copy. We’ll press whether that compounding advantage scales beyond the high end, or depends on it.
• The line on automation: “just because you can automate something doesn’t mean you should” is easy to say and hard to hold when automation cuts cost. Where Case actually draws that line, and what it costs him to hold it, is the test.

Hear from Steve Case alongside Airbnb’s Brian Chesky, Booking Holdings’ Glenn Fogel, and Intrepid Travel’s Darrell Wade, live at Skift Global Forum, September 22–24 in New York.