A Life Well-Lived: Inside the Evolution of Exclusive Resorts
An interview with CEO James Henderson on how The Club became a private platform for modern, meaningful living.
As originally written by Nick Copley for SherpaReport.
Once a category-defining idea in luxury travel, Exclusive Resorts has quietly evolved into something far more ambitious. In this conversation, CEO James Henderson explains how The Club’s reinvention — through experience, ownership, and community — has reshaped what it means to belong.
Let’s start with the big picture. Exclusive Resorts began with luxury travel. What has it become?
We’ve outgrown the idea of just being a vacation company. Yes, we started by simplifying luxury travel — private residences, hotel-level service, no hassle. But today, our Members want more than great trips. They want alignment — experiences that reflect their values, time spent with purpose, and a sense of continuity across their lives. We’ve become a lifestyle platform. A structure for how time is lived, not just booked.
You’ve described it as a “family office for your time.” What does that actually look like?
Our Members have wealth advisors. We help them manage something even more valuable — their time. That could mean curating travel, sure, but increasingly it means orchestrating a whole way of living. We’ve built a framework that moves with them through life. When you join in your 30s, it might be about flexibility. In your 40s, it’s shared time with family. By 60, it’s legacy — what you want to pass down. Concierge teams know your family’s rituals. Ambassadors understand what matters. And our experiences align with the questions you’re asking in each chapter. Travel is the entry point. What we offer is continuity.
You’re now developing branded residences. Why take that step?
It’s a natural evolution — not just of our portfolio, but of our philosophy. Sixty percent of our Members already own second homes. But what they want isn’t another asset — it’s consistency. The same service, same ease, same ethos they’ve come to expect from The Club, now in a home they own. Our first foray is Punta Cacique in Costa Rica. We’re partnering with world-class architects and designers to create properties that reflect a way of life, not just a destination. And we’re not new to this. We operate a $1 billion real estate portfolio around the world. That track record gives us credibility. What’s exciting is that these residences also introduce The Club to a new generation — owners who may discover us through real estate and then step into the larger ecosystem.
You recently assumed operations of onefinestay. What role does that play?
onefinestay gives us something powerful: flexibility in cities our Members already love — London, Paris, LA, New York. But it’s more than a convenience. It creates business synergies. Members can now list their own homes through a vetted, trusted platform. New customers can start with onefinestay and graduate into The Club. It opens a new front door — without compromising on quality.
You’ve said that travel is just the beginning. How do the experiences fit into that?
Experiences now make up over 20% of Member travel — and that’s growing fast. People want stories they can’t find on their own. Whether it’s a family sailing trip through the Galápagos or a behind-the-scenes moment at the Monaco Grand Prix, we handle every detail — visas, flights, private access. It’s white-glove, start to finish. But more than that, we help Members build a “Life List” — a personal blueprint for what belongs in this decade of life, not someday. That might mean a sabbatical. A cultural deep dive with their kids. A purpose-driven expedition. It’s not about checking off a bucket list. It’s about crafting a life.
A lot of your growth comes through referrals. Why do Members bring their friends?
Trust. Members invite friends because The Club has become part of how they live. It’s not something you casually gift — it’s something you believe in. We don’t need to mass-market. The experience speaks for itself.
You’ve called Exclusive Resorts a “community platform.” That’s not standard language for this space.
That’s by design. Our Members aren’t looking for more “stuff.” They’re looking for meaning, connection, shared values. And we’ve been building that — quietly — for over two decades. This isn’t a social club cobbled together in a strategy deck. It’s something real, born of the people who join and the moments they share. When Members host a dinner in Provence or show up for a philanthropic trip to Africa, it’s not performative. It’s personal. Loyalty like that can’t be engineered.
How do you nurture that at scale?
We keep things small, even when they’re not. Our teams know Members well enough to connect them in thoughtful ways — by interest, life stage, or shared goals. We host intimate dinners. Curate meaningful group travel. And even the podcast, A Life Well-Lived, plays a role. It sparks the kinds of conversations our members are already having — about time, values, and what it means to live well.
So what’s next?
Depth over breadth. Every decision we make comes back to one question: does this make our Members’ lives better — richer, fuller, more connected? If it does, we build it. If not, we don’t. That means new branded residences in places like Deer Valley and Big Sky. Possibly a dedicated concierge layer. A more bespoke, high-touch travel offering. We’re also open to acquiring brands that complement The Club and expand our ecosystem. onefinestay wasn’t a one-off — it was a signal. We’re growing with intention. Because we’re not trying to be relevant this year. We’re here to matter for decades.
