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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

business entrepreneurship

All Episodes

53:55

From Side-Hustle to National Hospitality Brand: How...

Behind the Stays ·

2024/09/20

Meet Rena Pacheco-Theard, co-founder of Boutiq, a vacation rental management company that’s blending tech with high-quality guest experiences to transform the industry. From starting Boutiq as a side hustle to enrolling in an Autsin-based startup accelerator, to running a nationwide portfolio, Rena shares how her team has harnessed technology, like their custom revenue management algorithm, to optimize every property. Tune in to hear how Rena is driving innovation in vacation rentals, using

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31:01

How to Finance and Underwrite Unique Stays:...

Behind the Stays ·

2024/09/17

In this episode, you’ll meet Shari Heilala — the founder of Sage Outdoor Advisory, an appraisal services consultancy for campgrounds, glamping resorts, and experiential hospitality companies. With over 30 years in commercial real estate, Shari shares her journey from valuing hotels at Cushman & Wakefield — one of the world’s largest commercial real estate services firms — to becoming a leader in the unique stays space, helping hospitality entrepreneurs navigate the complexities of financing and

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50:01

How She Turned 17 Acres of Raw Land in West Virginia...

Behind the Stays ·

2024/09/13

Meet Corinne Traub, founder of Firefly Ridge, a 17-acre magical glamping escape just 90 minutes outside of Washington D.C in Berkeley Springs, WV. What started as a dream to bring people closer to nature without the hassle of traditional camping quickly evolved into a thriving business that draws guests from across the Mid-Atlantic. In this episode, Corinne opens up about the long search for the right land, the challenges of building 14 luxurious canvas tents, mastering the art of hospitality, and

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49:31

Unlocking the Future of Hospitality: Tech Gaps, AI,...

Behind the Stays ·

2024/09/06

Meet Francois Gouelo, the founder of Enso Connect, a guest engagement platform that’s reshaping the short-term rental space. The story behind the founding of Enso Connect starts with a $5,000 mishap during a stay at a vacation rental stay — you’ll have to listen to the full pod for the deets. During our conversation, Francois argues that there's still a major gap in tech innovation in hospitality despite the proliferation of property management systems, guest experience tools, and smart locks. We

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01:00:08

How to Start and Scale an Airbnb Co-Hosting Business...

Behind the Stays ·

2024/09/03

Meet Jeremy Werden, an entrepreneur who has figured out the secret sauce to scale short-term rental co-hosting businesses successfully.In this episode, Jeremy and I dive into Jeremy’s journey, from his early days as a college student trying to make the UNC basketball team starting a small boat rental business on the Lake of the Ozarks in 2018. Tune in to hear how Jeremy leveraged his experiences, from failed startups to managing high-demand properties, to build a portfolio that continues to thrive

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49:02

How Four Unique Stays in New England Came Together to...

Behind the Stays ·

2024/08/30

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 alliance of creators and hosts across New England for a Fall Creator Road Trip. Kerri takes us behind the

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32:52

3 Lessons the Next Generation of Hospitality...

Behind the Stays ·

2024/08/27

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 mention Behind the Stays during your discovery call, you’ll get 10% off any service level option. If

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52:35

Building at the Intersection of Vision and Value: How...

Behind the Stays ·

2024/08/20

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 their fathers ignited a fire within them to pursue a different path—one that offered more than just

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01:06:18

Unlocking a Billion-Dollar Opportunity: Stories and...

Behind the Stays ·

2024/08/16

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 decided to build something better. In this episode, we chat about: How Lorraine turned a personal

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36:55

10 Entrepreneurs Building the Future of Hospitality...

Behind the Stays ·

2024/08/09

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 Schulman Havemeyer — Beach Plum Janice Smith — Cozy Rock David Garber — BrandyWine Grove Amber

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01:06:03

Breaking the Influencer Mold: Hot Takes on Content...

Behind the Stays ·

2024/08/06

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'll explore: How Krystal and Eric transitioned from traditional travel to full-time van life. The

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27:57

5 Big Ideas for Entrepreneurs Who Want to Build the...

Behind the Stays ·

2024/08/02

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 and the team at The Content House is that they truly understand this. They care about getting to know your

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01:05:50

From Air Force Officer to Hospitality Entrepreneur:...

Behind the Stays ·

2024/07/30

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 him to discover his passion for real estate and hospitality. In this episode, Blake and I delve into his

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01:00:16

Hot Takes on Rental Arbitrage, Men's Luxury Footwear,...

Behind the Stays ·

2024/07/26

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 thoughtful design and exceptional guest experiences. We'll explore: Ben’s early start in finance and how it

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01:02:30

The Rise of the Professional Airbnb Creator: Ideas,...

Behind the Stays ·

2024/07/23

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 influencers and content creators to share ideas, collaborate, and discuss industry trends. In this conversion,

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01:03:45

How to Make Loyalty Programs Work in Vacation...

Behind the Stays ·

2024/07/16

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 its high-quality homes and exceptional guest experiences. In this episode, Matthew and I discuss: The

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01:04:18

How a South African Game Ranger Became Glamping's...

Behind the Stays ·

2024/07/12

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 the vast expanses of Kruger National Park as a game ranger and nature conservationist. In this episode,

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01:02:13

How to Build a Nationally Recognized Vacation Rental...

Behind the Stays ·

2024/07/09

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 mission to professionalize vacation rentals by focusing on the essential aspects of a stay: bed, bath,

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21:37

We've Got a HUGE Announcement — Sponstayneous is Now...

Behind the Stays ·

2024/07/08

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! StayWatch brings you the best deals on Airbnb, Vrbo, and Booking.com that match your travel

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01:11:21

How He's Building a No-Fee Booking Platform for...

Behind the Stays ·

2024/07/02

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. Eric’s entrepreneurial journey didn’t stop there. After selling bedandbreakfast.com and later reacquiring

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325 results

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