Imagine owning so many homes around the world that you lose track of them—so instead of letting them sit empty, you hire someone to manage them, curate them, and quietly offer them to an elite circle of travelers who can afford $20,000-a-night stays.

If that’s the world you live in, you might hire Wolf Worster lives in.

As the founder of Sirreti, a private network shaping the ultra-luxury villa and private residence industry, Wolf works with high-net-worth individuals, property managers, and travel advisors to create the most exclusive stays on the planet — homes so private and so pristine, they don’t even appear on public listings.

One of his clients? Michael Dell, the billionaire founder of Dell Computers. That’s the level we’re talking about here.

But what makes a property truly ultra-luxury? And how has high-end travel changed as younger billionaires step onto the scene, throwing traditional expectations out the window?

In this episode, we explore:

• The secret world of ultra-high-net-worth travel — where money is almost meaningless, but privacy and exclusivity are everything.
  
• Why younger billionaires travel differently — from tech founders to heirs of generational wealth, how their spending habits and preferences are reshaping luxury hospitality.
  
  
• How Sirreti is redefining luxury standards — and why even the wealthiest travelers don’t just want high thread-count sheets; they want a story, an experience, and a seamless booking process.
  
  
• The hidden flaws in ultra-luxury hospitality — from outdated tech to service inconsistencies, and why the highest-end stays still struggle with guest experience.
  
  
• The role of travel advisors in this elite world — why they’re more important than ever, and why smart operators are shifting away from OTAs and direct bookings to focus on this lucrative channel.
  
  
• The rise and fall of luxury markets — why Ibiza and St. Barts are struggling while other under-the-radar destinations are thriving.
  
  
• Why there’s still no “Ritz-Carlton” of private stays — and what it would take to build a recognizable ultra-luxury brand in the vacation rental industry.

Connect with Wolf
Explore Sirreti 

Behind the Stays is brought to you by Journey — a first-of-its-kind loyalty program that brings together an alliance of the world’s top independently owned and operated stays and allows travelers to earn points and perks on boutique hotels, vacation rentals, treehouses, ski chalets, glamping experiences and so much more.

Your host is Zach Busekrus, Head of the Journey Alliance. If you are a hospitality entrepreneur who has a stay, or a collection of stays with soul, we’d love for you to apply to join our Alliance at journey.com/alliance.