The Mack Podcast How Expectations Are Changing in Luxury Travel
Mar 27, 2026
Rob Della Bovee, owner of a top Virtuoso agency serving UHNW clients; Shelby Donley, former Virtuoso leader building UHNW advisor services; Ben Vaschetti, co-founder of Maison Benjamin for family-office lifestyle management; Kristen Oliveri, CEO of Wealth Reimagined for rising generations of wealth. They discuss trust and seamless execution, contingency planning and 24/7 problem solving, multigenerational tailoring, authenticity versus curation, sustainability and AI’s role.
AI Snips
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Transcript
Episode notes
Sell By Describing Nighttime Failures Prevented
- Explain value during sales by naming specific failure scenarios clients avoid, like overnight support for flight disruptions.
- Rob Della Bovee tells new clients they can call at 3 a.m. and a staffed team will handle emergencies so principals sleep easy.
Plan MultiGen Trips As Individual Trips Within One Trip
- Structure multi‑gen trips as one overarching itinerary with individual sub‑itineraries so each member gets tailored experiences.
- Shelby Donley recommends treating each traveler as a separate file within the big trip and gifting touches like a photographer.
Authenticity Means Local Interaction Not Isolation
- Authenticity doesn't mean isolation; clients want local interaction that feels genuine rather than staged exclusivity.
- Rob and Shelby note demand for authentic F&B and local experiences has tripled compared with 10–15 years ago, increasing out‑of‑property programming.