Behind the Stays

We’re live at Skift with a builder proving the future isn’t generic search; it’s purpose-built marketplaces for travelers who already know their stay type—a lake house. I’m Zach, and today I’m joined by David Ciccarelli, co-founder of lake.com. After a startup exit during the pandemic, David and his wife (and co-founder) Stephanie bought a lake house—he grew up on Lake Superior, she on Lake Erie....

It’s 2008. The financial world is crumbling, Wall Street is bleeding jobs, and a brand-new finance grad named Andreea Grigore is staring down a recession with no clear path forward. Then, at a birthday party in Montreal, everything changes. She meets the founder of Luxury Retreats, one of the world’s first platforms for high-end villas, private islands, and over-the-top vacation rentals. A casual...

What do a high school jock turned Danny Zuko, a lung-collapse survivor in the middle of the 2008 crash, and a bourbon-country hotelier have in common? Will Hardy. In this episode, Zach sits down with Will — a creative entrepreneur, real estate maverick, and placemaker behind The Trail Hotel in Bardstown, Kentucky — to unpack a life defined by bold pivots, relentless grit, and audacious vision. Fro...

Brad Steward didn’t just ride snowboarding’s first wave—he helped make it. As a teenage builder-rider-organizer, he pushed the sport from outlaw to organized, working alongside Jake Burton and Tom Sims, lobbying the Forest Service when resorts said no, and helping pave the path that led to Nagano. He co-founded one of the early camps where an eight-year-old Shaun White showed up—years before the w...

He grew up in the Cook Islands, left for business school, and planned on a career far from home—until a family visit collided with a national crisis. The government was broke, tourism was collapsing, and the prime minister asked him to help. Tata Crocombe wrote a recovery plan, stepped in as an accidental hotelier, and rebuilt from the ground up—stabilizing a flagship on Rarotonga and later growin...

Some people chase clout. Scott Eddy collects humans—and turns conversations into careers. He’s the guy who can turn a DM into a deal, a walkthrough video into a booking, and a dinner into a decade-long partnership. He doesn’t posture. He shows up. Early. Today, I’m joined by Scott—hard to label by design. A Wall Street closer who hates the word "expert." A self-proclaimed non-golfer in a loud shir...

Picture this: a candlelit living room in New York, a guest list cast like a film, and a host who knows exactly who should meet whom—and why. That’s Erin Hosler. Before she checks a rate code or a P&L, she curates people. She trained at The Ritz-Carlton before the Marriott acquisition. Learned stagecraft under Ian Schrager. Honed the five-senses playbook with Andre Balazs. Sharpened her eye alo...

Some people chase opportunities. Ben Uyeda manufactures them from thin air. He’s the kind of mind who can turn a single YouTube video into a global audience, a shipping container into a home, and an empty stretch of desert into a 65-room design-forward hotel. His career isn’t a straight line — it’s a series of bold leaps, each one bigger and riskier than the last. Today, I’m joined by Ben — a man...

What would possess two brothers — with no hospitality background — to open a luxury hotel in a city where no new hotel had been built in three decades? In a word: vision. In this episode, I sit down with Shamim Ehsani, co-founder of Tribe Hotel and one of the most intentional hoteliers I’ve ever met. What started as a need for a conveniently located place for business travelers became something mu...

In today’s episode of Behind the Stays, we’re diving into one of the biggest mysteries plaguing modern hospitality entrepreneurs — how do you take all that beautiful, buzzworthy content that’s racking up views on Instagram and actually turn it into real bookings? My guest today is Dustin Baker, the quietly brilliant force behind Hidden Gem Media — a performance-driven marketing agency that’s helpi...

When you need real talk and real data on the glamping industry, there’s one person you call — and her name is Shari Heilala. In this episode, I sit down with the “godmother of glamping” for a deep dive into Sage Outdoor Advisory’s just-released Q2 USA Glamping Market Insights Report — the most comprehensive data set on the U.S. glamping market to date. We unpack how Shari and her team are filling...

Today I’m thrilled to be joined by Brandon Gore—someone whose life journey seems like it’s packed enough experiences for several lifetimes. Brandon’s story is anything but ordinary: from leaving high school behind at 17 to opening hotels, scaling sales operations across multiple Marriott properties, and then making the boldest leap yet—founding his own concrete design company. But here’s where thi...

Today is a special episode because Journey is officially live! I’m thrilled to sit down with John Sutton, the visionary founder of Journey, to talk about how this groundbreaking loyalty platform for independent hotels and private rentals came to life.  We’ll dive into John’s original inspiration, discuss the future of guest loyalty, and highlight the incredible Alliance Partners who’ve joined us e...

Today, I’m thrilled to share a conversation with someone I’ve admired from afar for quite some time — Bashar Wali. If you’ve spent any time in the hospitality space, chances are you’ve come across Bashar’s work — or at least his words. He’s the former President and CEO of Provenance Hotels, and today he leads two companies he founded: Practice Hospitality, a management company focused on culturall...

I’ve long admired Salt Hotels — their properties, their presence, their ability to make the familiar feel completely new. So when I had the chance to sit down with David Bowd, the visionary behind the brand, I knew we were in for something special. David’s story begins not in a boardroom or luxury suite, but in a small café his mother bought when he was a kid. It was there he discovered the energy...

In this episode, Zach sits down with Shaun Shirazian, CEO of Lodgify, for an unfiltered conversation about what’s next in hospitality tech—and what’s not changing. Shaun shares how a meaningful moment on a San Diego balcony more than a decade ago sparked his passion for short-term rentals, and how that guest connection still drives his work building tools for small operators around the globe. We u...

Welcome back to our special two-part series recorded live at the VRMA Executive Summit in Miami Beach. This gathering brought together some of the sharpest minds and boldest voices in vacation rental management, and we made it our mission to capture real-time insights on what’s top of mind for the leaders shaping this space. In Part 2, we continue our hot-take conversations with a new lineup of in...

Welcome to a special two-part series of Behind the Stays — recorded live at the VRMA Executive Summit in Miami. I brought my mic to the halls of one of the vacation rental industry’s most intimate and influential gatherings — and instead of long-form interviews, I asked a handful of sharp operators and thought leaders three punchy questions: What’s a contrarian belief you have about what today’s t...

James McBride is not just a hotelier — he's a visionary storyteller, a daring innovator, and a relentless champion of authentic luxury experiences. What started as his bold vision to redefine hospitality on a remote Indonesian island has become an award-winning global phenomenon, with Nihi Resorts capturing the imagination of travelers worldwide. As the co-founder of Nihi alongside legendary seria...

If you’ve ever dreamed of running marketing for one of the most iconic resorts in the Caribbean—or just wanted a peek behind the scenes of what it actually takes to make a destination “hot”—today’s episode is for you. My guest is Jason Kycek, the Senior Vice President of Sales and Marketing at the legendary Casa de Campo in the Dominican Republic. And while Jason’s resume includes time with some o...

What started as a furlough-era side project on Instagram is now a full-fledged media brand reaching over 400,000 boutique hotel obsessives — and Brandon Berkson, founder of Hotels Above Par, is just getting started. In this episode, we dive into: Brandon’s unshakable obsession with boutique hotels (he used to play hotel as a kid — not kidding) How a background in PR shaped his approach to storytel...

What happens when two childhood friends trade finance careers for a crack at building the next great American hotel brand? You get Trailborn. In this episode, I sit down with Mike Weiss and Ben Weinberg, co-founders and co-CEOs of Trailborn — a vertically integrated hospitality brand reimagining what it means to travel to America’s most iconic outdoor destinations. Mike and Ben didn’t just set out...

Cory Schisler isn’t just building beautiful hotels and restaurants — he’s rethinking what hospitality actually feels like. He’s worked with brands like Proper and Viceroy, co-founded The Madrona in Healdsburg, and has a sharp eye for the subtle — and not-so-subtle — ways hospitality has evolved (and where it still needs to catch up). In this episode, we unpack: – The early experiences that shaped...

Khalid Meniri didn’t come from hospitality — but maybe that’s exactly why he was able to see its most obvious blind spot so clearly. A designer and technologist by trade, Khalid is the founder of Selfbook , the beautifully elegant booking platform that’s quietly powering the next generation of high-end hotels. In this episode, you’ll hear the remarkable story of how a glass cube on Fifth Avenue (y...

Steve Carran never set out to become one of the most recognized voices in hospitality media. But what started as a scrappy experiment to engage hoteliers during his time in sales has now blossomed into The Modern Hotelier — one of the industry’s most beloved podcasts and a new video media brand that’s putting a fresh lens on hospitality storytelling. In this episode, you’ll hear the fascinating ba...