Choosing Flags: Raffles, Missoni, and Fit

Part I: AI and the Future of Hospitality

Every hospitality operator is asking the same question right now: what does AI actually mean for my business? Marc Lotenberg, founder of Dorsia, has a clear thesis: the operators who will define the next era of hospitality are not the ones who chase the technology, but the ones who double down on the art, the craft, and the magic that no algorithm can replicate.

In Part 1 of this episode, Marc shares why AI will finally deliver the hyper-personalized, frictionless experience that modern luxury has always promised, how it will change everything from the kitchen to the moment a guest walks out the door, and why the pace of that disruption is arriving far faster than most people in the industry expect.

This episode is made possible in partnership with Dorsia. To get access to Dorsia’s curation of impossible tables and cultural events, download the app and use code THESTANZA.

This interview was filmed at Cafe Carmellini in New York.

Part II: Early Conviction: Investing in Aman and the Future of Luxury Hospitality

Jonathan Goldstein is the founder and CEO of Cain International, a real estate investment and operating company managing over $14 billion in assets across luxury residential, hospitality, sports, and entertainment. Cain was formed in partnership with Todd Boehly and Eldridge Industries, built on a shared conviction that gateway cities and branded experiential real estate represented a generational investment opportunity.

Cain's real estate portfolio spans some of the most scrutinized assets in luxury hospitality. At the center of it is One Beverly Hills, a $5 billion, 17.5-acre mixed-use development flagged by Aman in the heart of Beverly Hills. Jonathan also co-led the $900 million investment into Aman Group alongside Saudi PIF, subsequently partnering with Mubadala Capital to finance the brand's expansion. Other assets in the portfolio include Six Senses Courchevel, Raffles Boston, the Delano Miami, and a stake in the Delano brand in partnership with Ennismore & Accor. Cain was investing in luxury and experiential real estate long before the pandemic made the thesis obvious to the broader market.

I worked on One Beverly Hills for Jonathan at Cain, which gives this conversation a level of access and specificity that is rarely present in interviews at this level of the industry.

Interview Highlights:

• Approach to risk and creating an asymmetrical outcome in business

• The story behind the Aman investment opportunity

• What sets Aman apart from the rest

• What it takes to earn the trust of sovereign wealth funds

• How Cain assembled the One Beverly Hills site

• The buyer profile of Aman Residences in Beverly Hills

• Developing other luxury projects: Six Senses Courchevel & Raffles Boston

• Repositioning the Delano brand & Miami hotel

• Jonathan’s approach to choosing a hotel management partner

• The personalization problem luxury hospitality has yet to solve

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Learn more about Cain’s portfolio here.

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