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PODCAST

Behind the Stays

Welcome to Behind the Stays — a podcast that shares the stories behind your favorite boutique hotels, short-term rentals, and hospitality brands and the hosts, operators, and entrepreneurs who’ve brought them to life. Every Tuesday and Friday you’ll meet the military veterans, retired flight attendants, tech entrepreneurs, school teachers, single moms, hoteliers, and real estate investors who are all, in their unique ways, shaping the future of travel and hospitality. Discover how these

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All Episodes

41:30

From Luxury Retreats to Building the Future of...

Behind the Stays ·

2025/09/23

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 conversation turns into an unexpected offer — and what was supposed to be a stopgap job becomes a

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55:11

How an Athlete-Turned-Actor-Turned-Entrepreneur Built...

Behind the Stays ·

2025/09/16

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. From sneaking into a high school audition that would change his trajectory, to flipping 800+ homes, to

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68:54

He Helped Put Snowboarding on the Olympic Stage,...

Behind the Stays ·

2025/09/09

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 world knew his name.Then Brad jumped lanes: into the Spike Jonze era of skate-culture

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57:39

How a Harvard MBA Became an Ai-First Hotelier

Behind the Stays ·

2025/08/29

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 growing a portfolio that now includes an acclaimed private-island resort on Aitutaki. Along the way, the

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58:07

How He Became Hospitality’s Most Interesting Voice on...

Behind the Stays ·

2025/08/22

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 shirt who lives in airports, hotels, and on cruise ships. An early Twitter force who became a breaking-news

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50:32

What Ian Schrager, Andre Balazs & Philippe Starck...

Behind the Stays ·

2025/08/19

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 alongside Philippe Starck. Then led chapters at The Standard Spa, Miami Beach; THE WELL in New York; Eaton

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01:06:20

The Wild Story Behind Joshua Tree’s First New Hotel...

Behind the Stays ·

2025/08/12

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 who defies simple titles. He’s an architect who never got licensed… yet co-founded an award-winning

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48:27

They Said a 5-Star Hotel Would Never Work in Nairobi....

Behind the Stays ·

2025/08/05

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 much bigger — a cultural reset for what luxury means in Kenya. We dive into: Why Tribe wasn’t designed to

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55:31

Viral Doesn’t Pay the Bills: How to Turn Social...

Behind the Stays ·

2025/07/25

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 helping some of the most design-forward vacation rental and boutique hotel brands in the world unlock direct

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44:55

The State of Glamping in 2025: Trends, Premiums, and...

Behind the Stays ·

2025/07/22

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 the gaping holes in industry data with hard-earned, operator-grade insights — from average daily retail

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56:39

Building a Timeless Boutique Hotel by Hand (and...

Behind the Stays ·

2025/07/18

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 things get even more fascinating. Brandon didn’t just stop at concrete countertops or sinks. Inspired by

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15:38

The Journey Begins: Journey is Officially Live!...

Behind the Stays ·

2025/07/10

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 early on this journey. Journey unites unique, independent hotels and private rental homes, offering

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01:04:15

How to Make Hotels Cool Again: What the Best...

Behind the Stays ·

2025/07/07

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 culturally resonant independent hotels, and This Assembly, a hospitality think tank and incubator building what's

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56:45

The Art of Growing a Hotel Brand Without Losing the...

Behind the Stays ·

2025/06/27

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 of hospitality — the joy in unpredictability, the beauty of serving others, and the sense of belonging

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55:09

Booking the Future: PMS, AI, and the War on Clunky...

Behind the Stays ·

2025/06/20

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 unpack Lodgify’s long-standing mission to “arm the underdogs” by empowering independent hosts and

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51:42

Live From VRMA's Exec Summit: What the Smartest...

Behind the Stays ·

2025/06/13

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 industry experts, diving into the themes of value-driven travel, AI-powered revenue strategy, and the

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42:10

Live From VRMA's Exec Summit: What the Smartest...

Behind the Stays ·

2025/06/10

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 travelers actually want from a vacation rental? What’s something happening in the industry that not

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01:08:02

Epic Stories & Insider Insights from Hospitality...

Behind the Stays ·

2025/06/06

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 serial entrepreneur Chris Burch (co-founder of Tory Burch), James is at the heart of this extraordinary

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01:01:08

The New Rules of Resort Marketing: Entertainment,...

Behind the Stays ·

2025/06/03

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 of the most respected names in hospitality, what makes this conversation so refreshing is that Jason is a

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51:26

How a Boutique Hotel Obsession Became a Global Travel...

Behind the Stays ·

2025/05/30

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 storytelling, strategy, and aesthetic curation The origin story behind Hotels Above Par — and how a single

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