Behind the Stays

Meet Kerri Gibson, the founder of  Chalets Hygge, a collection Scandinavian-style cottages located in the heart of Quebec's Eastern Townships. In this episode, Kerri and I discuss an amazing collaboration that's reshaping how boutique hospitality entrepreneurs can market their properties.  Kerri, along with Monique DeLorenzo from The Vermont A-Frame, have worked together to organize a strategic al...

In this episode, Zach shares three ideas inspired by Isadore Sharp, Founder of Four Seasons that today's hospitality entrepreneurs can and should take note of as they build  their businesses.  This episode is brought to you by  Hudson Creative Studio  — the leading web design agency for vacation rental managers.  Hudson Creative  is offering a special deal for Behind the Stays listeners. When you...

Meet Diana Ossa Sierra, co-founder of D-I-FI, who, along with her husband Josh, is transforming the intersection of architecture, design, and real estate investment in the world of boutique hospitality. Originally architects and construction managers, Diana and Josh were deeply embedded in their demanding careers until a life-altering event in 2021 made them question everything. The tragic loss of...

Meet Lorraine Woodward and Adam Norko, from Becoming Rentable, a company on a mission to make short-term rentals genuinely accessible for everyone. Lorraine's story is deeply personal—she was born with muscular dystrophy and is the proud mother of two sons who also have the condition.  When traditional vacation properties couldn’t meet her family's needs, she didn’t just accept the status quo—she...

Today on the pod Zach highlights 10 underrated entrepreneurs creating next-generation travel experiences!  Give these incredible folks a follow... Justin Potts — Linear Magazine  Sara Roitman — Field & Lake  Nick Purslow — Posh Outdoors Boris & Susan — Lumen Camps  Hillary Flur — Folly Collection Matt Orley — Red Cottage (acquired businesses, memberships, etc.) Brian Meyer — FLOHOM Becca S...

Meet Krystal and Eric Nagel, the adventurous duo behind Nagel Media Company, who have seamlessly blended their love for travel and photography into a thriving media business. In this episode, we dive into their unique journey from living out of a rooftop tent to becoming full-time van lifers and content creators specializing in lifestyle photography for boutique hotels and short-term rentals. We'l...

In this episode Zach shares 5 big ideas for hospitality entrepreneurs to implement right now... These ideas could be HUGE. Holler at Zach if you're already building one (or more) of these.  This episode is brought to you by  The Content House   If you listen to this podcast, you likely care a lot about your brand. You care about building it thoughtfully and purposefully.  What I love about Nate an...

Meet Blake Dailey — a former Air Force officer turned boutique hotel entrepreneur. Growing up, Blake dreamed of being in the NFL. And while that never came to fruition, his love for sports instilled in him a sense of discipline and determination that would later fuel his entrepreneurial spirit. After a stint playing college football, Blake's interests shifted toward business, eventually leading hi...

Meet Ben Earley, an exceptional entrepreneur who has made waves across multiple industries—from finance to luxury footwear, and now, to innovative hospitality. In this episode, Ben takes us on his fascinating journey from Wall Street to the world of short-term rentals. As the co-founder of Holt, Ben is building a portfolio of unique and upscale Airbnbs and hotels that stand out for their thoughtfu...

Meet Jon Kreye, a professional creator and community builder in the short-term rental space.  Jon has become a prominent figure in this niche, known not just for his stunning content but also for fostering a supportive community among hospitality creators.  Jon recently hosted his fourth creator retreat in partnership with Nikki & Hayden from Journey More, where they brought together influence...

Meet Matthew Orley, CEO of Red Cottage , a premier platform and vacation rental brand for unique stays across the Northeast. Matthew's journey with Red Cottage started as a guest in 2012. Captivated by the brand's consistency, unique portfolio, and potential, he acquired the business in 2022. Now, as the owner, Matthew is on a mission to transform Red Cottage into a regional powerhouse, known for...

Meet Paul Zway, the incredible founder of Exclusive Tents , who is joining us live from the lush jungles of Belize.  Paul’s journey from a young boy fascinated with wildlife in South Africa to becoming a pioneer in the luxury glamping industry is nothing short of extraordinary. Raised among the snakes and wilderness of a rural community outside of Pretoria, Australia, Paul’s path led him through t...

Meet Ashley Ching, co-founder of Inhaven , a trailblazing company with ambitious plans to set new standards in the vacation rental industry.  If you've ever booked a vacation rental and found it lacking in comfort or consistency, you'll understand the frustration that led Ashley to start Inhaven. With a background in merchandising and a deep understanding of the hospitality sector, Ashley is on a...

I’ve got a huge confession to make… Something I’ve never admitted publicly before…EVER. Behind the Stays' parent company's name, Sponstayneous, sucks.  No one can say it right. We’ve been called everything from “spoon stayneous” to “spontaneously.” I’ve fought this so hard, but today, I’m here with my white flag. So, I’m here with exciting news — as of today, Sponstayneous is now StayWatch ! StayW...

Meet Eric Goldreyer , a legend in the world of travel and hospitality. Eric is the founder of bedandbreakfast.com, a platform he launched in the late '90s that revolutionized the bed and breakfast industry by bringing it online. At a time when most innkeepers relied on guidebooks and phone calls, Eric saw the potential of the internet and created the largest database of B&Bs in North America....

Meet Nathan and Michael, the founders of Howzit Hostels, who are revolutionizing the hostel experience in Hawaii today, and across the rest of the US tomorrow. Nathan and Michael, broadcasting live from the beautiful island of Maui, share their journey from real estate sales to creating upscale hostels that blend affordability with a boutique hotel feel. They dive into the origins of their busines...

Welcome to "Unlocking the Secrets of Successful Hospitality Websites: A Special 2-Part Series with Hudson Creative Studio.” In this series, I sit down with Eli Pritykin, founder of Hudson Creative Studio to dive deep into the art and science of creating a memorable website that serves as the digital headquarters for your hospitality brand. In the first episode , you'll hear Eli's fascinating journ...

In this episode, we welcome back Jamie Lane, SVP of Research at AirDNA, to discuss the booming trend of unique stays in the hospitality industry. Over the past few years, the demand for unique stays—think A-frames, yurts, and treehouses—has skyrocketed. Jamie and I delve into the data behind this trend, exploring how travelers' preferences have shifted towards distinctive and memorable accommodati...

Meet Omar Boubess, Creative Director at Studio Circa, a luxury branding agency that works with boutique hotels and unique collections of STRs. Growing up, Omar wanted to be a National Geographic photographer — or a soccer player — depending on the day you asked him. And, while neither dream quite came to fruition, Omar did pursue his creative interests and wound up finding a love for developing un...

Welcome to "Unlocking the Secrets of Successful Hospitality Websites: A Special 2-Part Series with Hudson Creative Studio .” In this series, Zach sit down with Eli Pritykin, founder of Hudson Creative Studio to dive deep into the art and science of creating a memorable website that serves as the digital headquarters for your hospitality brand. In the first episode, you'll hear Eli's fascinating jo...

Meet Ruth Wimpory — the entrepreneur behind Skoolie Stays and The Vacationist , two of the UK’s favorite off-grid escapes.  In 2019, Ruth and her husband, Guy, along with their two young children, decided to take a year off from their “normal” lives in Brighton in the UK, to embark on an adventurous year-long journey across the United States in a converted school bus.  What started as a quest for...

Meet Philip Kennard — Founder and CEO of Futurestay . Growing up, Philip loved video games.  And for Philip, video games were about so much more than the playing experience…he loved the art, the logic, and the business behind creating worlds.  This love sparked his entrepreneurial spirit and led him to work in game development for Sega, one of the world’s leading game design companies, and, eventu...

Meet Annie Holcombe, a seasoned hospitality industry expert with a passion for vacation rentals and an impressive track record at major travel tech companies. Annie's journey in the vacation rental industry is nothing short of inspiring. Starting from property management, she moved on to pivotal roles at Expedia and Homes and Villas by Marriott, gaining invaluable insights into the world of travel...

Meet Yvonna and Darren Grandfield, a dynamic duo who’ve turned their passion for real estate into a thriving business of unique and stunning short-term rentals. Growing up, Yvonna and Darren never imagined they’d one day be the proud owners of a collection of charming properties, but a chance encounter at an Ace Hardware store set them on a path they couldn’t have anticipated — who’d a thought the...

Meet Josh Luttrell, the innovative entrepreneur behind Home Theme Orlando, a company transforming vacation rentals into immersive themed experiences. As a kid, Josh dreamed of being a basketball player, but life had other plans. However, he took his competitive spirit and he channeled it into real estate, eventually carving out a niche in Orlando's short -term rental market by creating uniquely th...