Matt Talks Hospitality: Real conversations for innovative hoteliers

What if the room was the least interesting thing about your hotel? Jim Deters looked at a ski town in Colorado and decided to build something else entirely: a tribe. He is the founder and CEO of Gravity Haus, an adventure lifestyle hotel and membership club with properties across the Rocky Mountain West. Jim's a tech entrepreneur turned accidental hotelier, and someone who gives his general managers stock options, which tells you everything you need to know about how differently he thinks. Jim joins Matt to talk about the membership model, the tech stack, and how he's built something that guests are willing to pay for twice: once for the room, and once to belong.

Have lifestyle hotels gotten worse? Eric Jafari has built hospitality companies from the ground up across Europe, multiple times over. He co-founded Locke, edyn and Birch, led a £1.5bn pan-European development platform, and is now building AENDRE, a platform that acquires, develops and operates wellness and lifestyle hospitality brands. Eric and Matt get into the problem with lifestyle hotels, what it takes to raise capital for something disruptive, and what the next generation of hospitality looks like.

Up until a few years ago, Cole Rubin managed a $19 million residential portfolio of around 200 properties across Airbnb and Booking.com. He lived the midnight guest messages, the missed calls, the inbox chaos. That firsthand pain led him to build Conduit, an AI agent platform for hospitality. Guest requesting a late checkout? An agent checks availability, takes payment and updates the cleaning team, all without a human in the loop. Cole joins Matt to talk late checkouts, AI agents and the future of hotel guest communication.

How should small hotels think about building and investing in a tech stack when they don’t have the data, the team size or the budget of large properties? Elise Roberts is the Managing Director of Happiness Hospitality, the operator behind The Gallivant, a beautiful boutique coastal hotel in East Sussex that holds a MICHELIN key and VisitEngland's Small Hotel of the Year. Elise joins Matt to talk about why 18 systems are not too many for a small hotel, what every hotelier should ask before buying software and how independent properties can outrun the big chains.

Why can you order an Uber within seconds but booking a hotel room still feels like filing a tax return? That is the question Frédéric Robles could not let go of. A tech and antitrust lawyer at Sullivan & Cromwell and Amazon, he walked away from law in 2021 to build Namastay, a modern booking engine now live in over 400 hotels across 42 countries. He joins Matt to talk about why most hotels are stuck below 15 percent of direct bookings, and how payment optimization, including digital wallets like Apple Pay, can shift that number.