This Hotelier Is Reinventing The Hospitality Space

Photo Credit: Matt Kisiday

Photo Credit: Matt Kisiday

Tell me about your background, your brand, and what you are doing at Blue Flag Capital.

I’m one of those lucky people who knew early on that hospitality is what I wanted to do, from my earliest days getting exposure to the SoHo Grand hotel when I was in high school, to going to the hotel school at Cornell. After Cornell, I was a consultant in the hospitality real estate group at EY, working on everything from due diligence on luxury brand and real estate mergers to boutique hotel development projects in NYC. From there I joined Kimpton Hotels and Restaurants, and worked on both the management and private equity investment sides of the business. After Kimpton, I was part of the early team at Yotel, helping to pioneer the affordable luxury brand segment. At Yotel, I lead the brands growth, investment and development efforts globally – ultimately growing the brand to more than 3,500+ keys across Asia, UK/Europe and North America, which lead to Starwood Capital investing in the brand in 2017. In 2018, my business partners and I co-founded a private equity real estate business focused on investing in and creating unique boutique hotels in ultra luxury, high barrier markets. My partner, Brad Guidi, who heads up our design and development teams, and I have been focused on trying to put the soul back into hospitality through acquiring existing, but tired, hotels in high barrier luxury vacation markets and reimagining them through new branding, lighting, scent, sound, and, most importantly, telling a story through each new property. It’s unique today to have our own capital to acquire and own these hotels but also the ability to create new brands from scratch. That’s how Faraway was born, as an example. We purchased a collection of old captain houses, an 1880s quaker meeting house, and retail which we combined into what we think of as a boutique campus in the heart of downtown Nantucket. What we noticed at the same time is that people are spending more and more time in “their place” and thus traditionally seasonal markets are not only becoming less seasonal to an extent but also has real demand for boutique hotel and restaurant experience — on par with what our guests expect at great boutique hotels in the urban core, from New York, to LA, to London, or Paris.

Photo Credit: Matt Kisiday

What’s the reasoning for doing what you’re doing?

My goal has always been to put a little more light into the world. As hotels have become more institutional over the last 25 years, the bigger brands have started to gobble up all of the great boutique brands. As a result, we think there is white space to recreate what our hero’s — folks like Ian Schrager, Andre Balaz, and Bill Kimpton — did in the ’90s. But instead of that happening in SoHo, we think the opportunity today is in places like Nantucket or Sag Harbor where, post-pandemic, our guests are now spending most of their time.

In only a few years, you’ve done what most hoteliers can’t in decades. How do you think you’ve managed to do this?

I think the real secret to how we’ve been able to move so quickly comes down to two things. One: our focus on creating places for ourselves. We build, brand, and operate what we know, usually trying to fill a void that we can’t find, such as the cocktail club and lounge at Sister Ship at Faraway Nantucket or a nostalgic nod to summer aimed at both discerning adults but also for kids at the reimagined Beachside resort. Two: our small but mighty team of incredible people at Blue Flag. We all come from different backgrounds, some from the industry, some from residential backgrounds like Brad, and that brings a unique lens to what we have been able to do so quickly. We also are the number one guests at all our hotels, so I think people have really noticed that we are genuinely interested in creating places that are happy, fun and approachable while also being very design forward, high end and experiential. We are deeply intertwined with each location’s unique narrative and emotional essence. Inspiration at first sight is crucial for any property we consider. We seek a certain indescribable spark in each location. This profound attention to detail and dedication to local authenticity distinguishes Blue Flag in the fiercely competitive luxury vacation market. The philosophy transcends mere space creation; it’s about weaving an experience that is intrinsically interlaced with the local environment, ensuring each property is not just a place to stay but a destination that resonates with its setting. “We often say, ‘the experience is the souvenir’— and we mean it.

Photo Credit: Matt Kisiday

What do you think is behind the success of Faraway Hotels, which has won Michelin keys and has been awarded best hotels in the world in just a few years?

I think Faraway really hits a note because we combined high-end design with fun all in the backdrop of paying homage to the buildings and locations that we are in. Because we have such a long-term view, we go much further, and invest more capital, in these redevelopments than usual. That means that we take our time getting the right entitlements, and listening to guests and locals alike on how we can build something that enhances the overall experience of where we are and not just the property itself. And we build each Faraway with a unique story, which tries to create a sense that you are in someone’s vast home or estate vs a hotel or resort. That combination allows us to really deliver magic throughout your stay because there are so many layers and experiences to discover on your journey with us.

Faraway on Martha’s Vineyard brings an entirely new vibe to the island; it definitely stands out. What has been the feedback from guests? Locals?

Faraway MV is definitely a labor of love for us, and for me personally as I grew up going to Chappy as a kid and have been staring at the old Kelley House for most of my life. We spent over a year working with the town, locals, and our team before we started to redevelop the campus into what is now Faraway MV. The response has been really incredible, and I think it’s because we stayed true to what the property is (keeping the Newes from America pub, for example) but also really pushed the envelope with our design, new pool, and the Pelican Club. The best compliment that I’ve received recently was from a local family who opened a new high-design, high-end men’s clothing store up the street. They said that they would never have thought that Edgartown would accept something so high-end and boutique as Faraway, but once we lead the way, they opened and their new store which is thriving.

Photo Credit: Matt Kisiday

Why the name Faraway? How does the urban core campus translate in these markets?

The name Nantucket means “Faraway Land,” so we wanted to lean into that for the name. The campus idea came to us because we felt like there wasn’t anyone combining these amazing, usually historic buildings into a single branded experience, so we think of them as urban resorts in some of the most selective, luxury markets in the world.

I heard there is a private letter program at Sister Ship in Nantucket, inspired by the 1920s Paris Fitz and Hemingway trading notes. Love that!

Yes! This is a good example of how we try to infuse some soul back into our properties. My dad is a huge 1920s Paris fan, and would always tell me stories about Fitz leaving notes for Hemingway and their friends as they hopped from bar to bar trying to find each other. So, we bought a quill and some ink, got wax, and a Faraway mermaid seal and started writing letters to each other. Eventually other people noticed, and today if you ask the bartender, he’ll tell you about the letter program and let you write one. Next time you’re at Sister Ship, don’t forget to ask the bartender if you have Bar Mail; he’s probably got a letter for you behind the bar.

I heard celebrities have been frequenting your spaces. Any names you can share?

We host everyone from movie stars and singers, to locals, business titans, music/film and creative types. But while some have been kind enough to give us shout-outs, you’ll never catch us saying who they are. Discretion is at the heart of luxury boutique hospitality.

Photo Credit: Matt Kisiday

What is the future of the luxury hospitality space? How are you reinventing it and where do you see it going?

We believe that the future of luxury hospitality is focused first on where discerning guests are spending more of their time, which we believe to be in a handful of these types of markets. We are also seeing more corporate offsites happening, in smaller groups, in these places as well as more demand for private dining and small group gatherings in restaurants. It’s one of the reasons we have been so focused on adding more assets in places like Nantucket, Martha’s Vineyard, Greenport, Montauk, Sag Harbor, and Jackson Hole. The second is that as technology becomes more prevalent in everyone’s lives we believe that people will want an increased human touch to hospitality. Technology is a great way to help facilitate the backend of a guest journey but we believe that people want more interaction with our staff, not less going forward.

You say the “experience is the souvenir.” How do you focus on the scent, sound, and design of the properties to assure this?

When we think of experience, it’s not just creating signature scents, the right lighting, and music transitions throughout the day, but really providing delight and surprises throughout your stay — like finding out about the letter program at Sister Ship or the coins at the Newes from America pub. But more than anything, we hope that our teams are giving you a true sense that you are being hosted at these beautiful properties and giving you access to great food, an amazing bed, and the home base to then explore the incredible location that you are in.

What is your number one tip for success?

I’ve learned from some incredible mentors over my career, and the best advice I ever received was “kill your ego before it kills you.”

Photo Credit: Matt Kisiday