“In an AI discovery world, where Google, OpenAI, and chat interfaces can search across everything, the concierge layer forms above platforms, not inside them. Hotels, boutique inns, Vrbo, Booking.com, and direct-booked homes all sit in the same answer space. The listings get more comparable.”
“Airbnb can innovate on the interface: discovery, booking, messaging, policies, payments, essentially everything that happens before and after the stay. The actual stay is controlled by millions of hosts making millions of individual decisions about linens, repairs, air conditioning, noise, and checkout chores.”
“The one moment Airbnb does own is when things go wrong: refunds, chargebacks, damage claims, cancellations, the slow-motion arbitration of competing narratives about what happened in someone’s apartment at 11p.m. Airbnb functions less as a hospitality brand than as an adjudication system with a checkout flow. This is a structural problem, and no CTO can solve it.”
“A decade ago, the exciting short-term rental story was the wave of companies trying to fix the physical layer, with consistency, operations, quality control, and reliability. They weren’t marketplaces; they were trying to be hospitality companies.
Sonder went public via SPAC at a $2.2 billion valuation. By November 2025, Marriott terminated the partnership citing default and Sonder ended in Chapter 7 liquidation.
Vacasa was valued at $4.5 billion in 2021. Casago acquired it in April 2025 for approximately $130 million, a 97% collapse. The once-disruptor was eaten by a 5,000-property franchise operator.
Inspirato saw gross margins collapse from 71% to 31% in a single year. Exclusive Resorts absorbed them for $59 million.”
“These companies failed because hospitality is operations disguised as real estate disguised as tech. Short-term rentals look scalable until you meet the reality of cleaning coordination, maintenance, customer support, local regulation, and a product that physically degrades.”
Many more great strategic insights in the article by the one and only Rafat Ali, Skift Founder & CEO, Industry Icon, Global and Travel Expert!