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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

45:09

He Buys RV Parks: Predictions on the Future of...

Behind the Stays ·

2024/03/01

Meet Matt Whitermore, a hospitality entrepreneur who buys, builds, and manages RV parks. In this engaging conversation, Matt shares how he got started buying RV parks and why he believes there’s huge opportunity to disrupt and reimagine this category of travel and real estate investment. Tune in to hear: - The lessons Matt learned after buying his first RV park - How he see experiential hospitality and RV parks intersecting in the near future - Why camping is getting younger and cooler and the

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01:05:59

How to Build the Apple of Vacation Rentals:...

Behind the Stays ·

2024/02/27

Meet Kyle Tibbitts, Chief Marketing Officer at Wander, a network of smart, luxury vacation rentals that’s on a mission to verticalize the short-term rental experience.If you were to have asked Kyle as a 10-year-old what he wanted to be when he grew up, he would have told you a lawyer, which, today, Kyle would tell you would have been a huge mistake. But if you were to have asked Kyle what he wanted to be just a few years later, he would have told you an architect — from a young age he had a deep

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21:42

5 Ways OpenAI's Sora Will Revolutionize Hospitality...

Behind the Stays ·

2024/02/20

In this episode of Behind the Stays, Zach shares five tangible and tactical ideas for how OpenAI's new Sora model will fundamentally change hospitality entrepreneurship. Sora is an AI model that can create realistic and imaginative scenes from text instructions. Sora is able to generate complex scenes with multiple characters, specific types of motion, and accurate details of the subject and background. The model understands not only what the user has asked for in the prompt, but also how those

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41:17

How They Built a Cabin Collection That Landed in...

Behind the Stays ·

2024/02/16

Meet Stephanie Gutierrez, the creator of North Country Cabin Co. — a boutique collection of short-term rentals located just 90 minutes from Minnesota's twin cities in Comstock, Wisconsin. Growing up, Stephanie wanted to be an artist — her grandmother had an incredible eye for art and design and Stephanie dreamed of emulating her. And while she didn’t become a professional artist, her knack for creativity would wind up leading her to launch a boutique hospitality company in partnership with her

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58:22

So, Was the STR Wealth Conference Worth It? Here's...

Behind the Stays ·

2024/02/13

One of the newest and hottest industry events, STR Wealth Con, just wrapped last week — and we wanted to know what people thought about the event! In this episode, Zach sits down with Wil Slickers (emcee of the event), Sean Wilkinson (Co-Founder of Hostshare and first-time conferences attendee), and Heidie Henriksen ( a vacation rental industry veteran, to get their thoughts on the content, the community, and the networking at the event. Let us know what you thought of the event by joining the

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01:00:36

Building the Prequel to Airbnb: Jeremy Gall on the...

Behind the Stays ·

2024/02/09

Meet Jeremy Gall, Founder & CEO of Breezeway — the leading property care, operations and messaging platform for hospitality entrepreneurs. Growing up, Jermey wanted to be a professional basketball player. And while he never made it into the NBA, he did make it into Law School. But Jeremy’s professional career as an attorney wouldn’t last long because he was bit by that sneaky, but ever so enticing, entrepreneurial bug. Tune into hear the exciting story of how Jeremy co-founded and built

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55:02

She Wanted to Be a Cat, a Vet, or an Anesthesiologist...

Behind the Stays ·

2024/02/06

Meet Meaghan Moylan, Executive Director of Outpost — a Vacation Rental and Property Management company located in Jackson Hole, Wyoming. If you were to have asked Meaghan what she wanted to be when she grew up, she would have told you a cat, a veterinarian, a nurse, or a lawyer — depending on whether she was 3, 10, 15, or 18. As fate would have it, Meaghan did not become any of the aforementioned and, after graduating from college with a degree in public relations, decided she was going to move to

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44:58

Marriott’s Venture into Vacation Rentals: The Story...

Behind the Stays ·

2024/02/02

Meet Chris Stephenson, Vice President of Global Development at Marriott Homes & Villas. Chris has spent his career building new, innovative products and services across travel and hospitality. In February of 2019, Chris was a part of the founding team of Marriott Homes & Villas and in charge of thinking through how best to bring Marriott’s vacation rental home product to life. In this episode, Chris and I discuss: What it’s like incubating a new product offering within a legacy

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45:29

How She Designed a Luxury Haven in the Blue Ridge...

Behind the Stays ·

2024/01/30

Meet Taylor Bates, the creator of The Afton House — a stunning, luxury home made for gathering and nestled in the heart of Virginia wine country. Growing up, Taylor wanted to be an architect or a Fortune 500 CEO — she’s always loved the intersection of marketing, design, and business. After working in a few marketing management and nonprofit leadership roles, Taylor wound up starting her own boutique interior design firm focusing on residential and commercial projects. And it was around this time

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48:55

He Dreamed of Being a Farmer, But Wound Up An...

Behind the Stays ·

2024/01/26

Meet Scott McIntosh, Co-Founder of Back Forty Glamping, a luxurious glamping oasis on 26 acres of land in Meaford, Ontario. Growing up, Scott wanted to be a farmer — he loved being outdoors and the notion that you could make a life from tilling fields and harvesting crops was incredibly attractive to him. And while Scott wound up pursuing a career as an educator instead, a few years ago he and his brother Ben had an idea which would enable Scott to trade the classroom for the great outdoors… And

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42:10

How He's Reimagining Outdoor Hospitality Through the...

Behind the Stays ·

2024/01/23

Meet Dylan Barahona, General Manager at Canyon of the Eagles, a nature resort and preserve on 940 acres of land, located just 1.5 Hours from Austin, Texas. If you were to have asked Dylan at ten-years-old what he wanted to be when he grew up, he’d tell you either a professional baseball player or a chef. And while neither of those dreams quite panned out, the latter, dream set him on path to pursue a career in hospitality, and, over the last decade, Dylan has become a highly-regarded and respect

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50:01

How They're Building the Hottest New Tiny Home: The...

Behind the Stays ·

2024/01/19

Meet Antonio Gonzalez, President of ÖÖD House — the company behind the instagram famous mirror houses. Antonio is an engineer by trade, but always had a heart for entrepreneurship… So, when the opportunity to co-found Jupe along with past-podcast guest Jeff Wilson and take it through Y Combinator, the world’s most prestigious of startup accelerators, came about, he took it. Antonio learned SO much from the accelerator where the Airbnb founders also graduated from and had an incredible couple of

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49:14

From Music Producer to Hospitality Entrepreneur: The...

Behind the Stays ·

2024/01/16

Meet Garett Brown, the visionary and creator behind Cameron Ranch Glamping, a collection of luxury glamping units on 11 acres just an hour outside of Houston, Texas. Garrett is a professional music producer and traveling DJ who has always loved dabbling in real estate investing. When he wasn’t performing on stage or out on a tour, he’d find himself scrolling through listings dreaming of what it’d be like to build his own portfolio of homes. He wanted to learn more about real estate so he decided

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55:21

Meet the 19-Year-Old Who Builds (and Buys) Unique Stays

Behind the Stays ·

2024/01/12

Meet Brett Deas, a 19-year-old entrepreneur who owns and operates unique stay vacation rentals across the U.S. While his high school buddies were scrolling through TikTok before school and playing video games afterwards, Brett was binging Bigger Pockets podcasts to understand the world of real estate investing. After graduating from high school, Brett decided to try his hand at real estate investing and entrepreneurship before pursuing a college degree. And so far? That decision is paying off

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51:12

The New Era of Exploration: How Today’s Travelers...

Behind the Stays ·

2024/01/09

Meet Mollie Reese, the host of the popular Stay in Good Company podcast and an experienced community builder who has spent her career working with leading brands across the the food & beverage and events & hospitality industries. Having recently left the world of corporate burnout and the hustle and bustle of city-living behind for a slower way of life, Mollie set out to pursue personal passions in travel. Throughout her journey, she is in search for authentic stories to share, curious

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46:27

How He Built the Uber for STR Cleaning: The Story of...

Behind the Stays ·

2024/01/05

Meet Assaf Karmon, Co-founder & CEO of Turno — a marketplace that helps vacation rental hosts and property management companies simplify and automate cleaning. Assaf was born and raised in Israel and as a kid his dream was to be a professional soccer player. And while that dream never came to fruition, in part because Assaf spent most of his early sports career sitting on the bench, the determination, boldness, and focus he garnered as a child trying to level up his game, has enable him to

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55:14

How They Transformed a 100-Year-Old Beach House into...

Behind the Stays ·

2024/01/02

Meet Jake and Leslie, the creators of the Lighthouse Cottage, an oceanfront escape in Cape May, New Jersey. Jake and Leslie had always dreamed of owning a beach house, but acquiring a property in the competitive Cape May market seemed out of reach. That is until one day Leslie was scrolling on Zillow and noticed a new listing for a 100 year old property located right on the beach. The home clearly needed a lot of work but something about its character spoke to Leslie…and within hours she had called

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52:32

Reflections and Ideas on Leadership, Branding, and...

Behind the Stays ·

2023/12/19

Meet Rob Patterson, an incredible hospitality leader whose most recent post was as the CEO of Best Western in the United Kingdom. Rob grew up in a very remote town in the country of Australia. Growing up, Rob dreamed of becoming a professional footballer — so much so that when an opportunity to move to Sydney to pursue his dream came to fruition, he left home without thinking twice. And while he never wound up playing football professionally, Rob did stumble into another profession while living in

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51:27

How to Merge Luxury, Sustainability, and...

Behind the Stays ·

2023/12/15

Meet Amber and Charlie Pledge — the founders of Kabn Company, a new hospitality brand focused on creating luxurious, and sustainable nature-immersed escapes. Amber and Charlie have always loved to travel. The couple has been fortunate enough to live and work in major hubs of innovation like London, San Francisco, and Dubai. And while Amber and Charlie both love working hard, climbing the corporate ladder just started to feel, well, a bit unfulfilling. Tune in to hear the story behind how this

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52:31

He Worked in Luxury Hotels for 20 Years — Now He’s...

Behind the Stays ·

2023/12/12

Meet Steve Turk — a decorated professional who has spent over two decades working in luxury hospitality. Steve’s father was a susccessful attorney. From time to time, his dad would bring him along on work travel and Steve remembers being in total awe at the hotels he and his dad would stay in. There was something so magical about walking into an ordnately decorated hotel lobby and being greeted as if you were some kind of royalty that left a significant impression on Steve. As Steve began thinking

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329 results

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