From World Traveler to Boutique Hotelier: Lessons Learned on Owning Both Vacation Rentals and Hotels

Meet Adam Dailey – an adventurous soul and hospitality innovator who owns a collection of short-term rentals and boutique hotels in San Diego.

From an Olympic sports tour operator to a global family traveler, Adam’s journey into hospitality began with a family sabbatical, taking him, his wife, and their four young children around the world. 

Today, Adam channels that passion for exploration and authentic experiences into managing boutique hotels and vacation rentals that blend charm, service, and design to create truly memorable stays.

In this episode, we dive into:

• Adam’s journey from corporate burnout to launching a hospitality portfolio inspired by his global travels
• His pivot from owning and managing vacation rentals to owning and managing boutique hotels
• Why he believes smaller, well-designed properties (20-30 rooms) allow for an exceptional level of personal service
• Lessons learned from his partnership with Sonder, and the difference between low-touch, tech-driven stays and high-touch, luxury-focused hospitality
• Why the right touchpoints—like an on-site concierge or thoughtful lobby design—create a feeling of true luxury, even in boutique settings
• Adam’s insights on navigating the evolution of guest expectations in a saturated market where unique stays are in high demand
• The role of AI and technology in optimizing operations, without sacrificing the human element that guests crave

Alright friends, without further ado, get ready to meet Adam. 

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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 joinjourney.com/alliance.