Behind the Stays StayWatch

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 fueled his entrepreneurial spirit.
The story behind his luxury men’s shoe brand, Paul Evans, and the transition to hospitality.
Why Ben is building his portfolio overseas, focusing on markets like Romania, Mexico, and Greece.
His hot takes on "rental arbitrage" and why he prefers the term "commercial vacation rental."
How Holt is vertically integrated, giving them unparalleled control over their properties and guest experiences.
Get ready to hear how Ben's innovative approach is setting new standards in the hospitality industry and why he believes in creating spaces that are more than just a place to stay—they’re experiences in themselves.
Connect with Ben on Twitter
Connect with Ben on LinkedIn
Learn more about HOLT
This episode is brought to you by our friends at Turno. 
Turno is the smartest way to schedule, pay, and find vacation rental cleaners — think of Turno as an Uber or Task Rabbit for STR hosts. 
Simply create an account, describe your listing’s cleaning needs, and Turno will match you with cleaners near you. 
Turno offers simple, affordable pricing for STR hosts of any size. Single property accounts and Marketplace users get access to all the platform’s tools and features for FREE. And they make working with your existing teams easy too, with plans as low as just $6/month per property.
Learn more and earn a $150 Amazon Gift Card after you complete your first cleaning. 
Want to book a consulting brainstorm with Zach?
Send him an email directly at zach@sponstayneous.com or complete this payment link and get immediate access to his schedule where you can book some time with him!
About the Show
Behind the Stays is brought to you by StayWatch — the internet's best resource for deals on Airbnb, Vrbo, and Booking.com. You can subscribe, for free, at www.staywatch.ai
Behind the Stays is hosted by Zach Busekrus, Co-founder of StayWatch, you can connect with him on Twitter at @zboozee or on LinkedIn.  
 
 

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, Jon talks about the evolution of creators in the Airbnb and greater hospitality space, the challenges and opportunities within the creator economy, and the importance of professionalizing the role of hospitality content creators. 
He shares insights on how creators can differentiate themselves, the significance of setting professional standards, how hosts and vacation rental managers can best engage with creators and the strategies that help separate the best creators from the rest of the pack.
Discover how Jon and his peers are navigating the complexities of pricing, the value of collaboration over competition, and the exciting potential for partnerships with hospitality brands. Whether you're a property manager looking to enhance your marketing or a creator seeking tangible ideas for how to grow your business, this episode is packed with valuable insights and actionable takeaways.
Connect with Jon on Instagram 
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 style, your approach, and the unique quirks and features that make your collection of stays special. 
Their service is full end-to-end social media management and content creation. From shooting stunning videos and photos to editing, posting, and even sourcing influencers to partner with…
The Content House specializes in working with hospitality entrepreneurs building well-branded, boutique collections, often in exotic or extra-special locations…
Follow The Content House on Instagram
Dunlap Hollow ReelLive Oak Lake ReelFLOHOM ReelVilla Stay Texas Reel
Want to book a consulting brainstorm with Zach?
Send him an email directly at zach@staywatch.ai or complete this payment link and get immediate access to his schedule where you can book some time with him!
About the Show
Behind the Stays is brought to you by StayWatch — the internet's best resource for deals on Airbnb, Vrbo, and Booking.com. You can subscribe, for free, at www.staywatch.ai
Behind the Stays is hosted by Zach Busekrus, Co-founder of StayWatch, you can connect with him on Twitter at @zboozee or on LinkedIn. 

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 origin story of Red Cottage and its evolution over the years
The innovative membership program Red Cottage launched, which is designed to foster loyalty and make last-minute getaways even more 
Insights into acquiring vacation rental management companies — Red Cottage just acquired Posto
The importance of maintaining brand authenticity while scaling
The biggest opportunities for hospitality entrepreneurs right now to build, buy, and sell businesses 
And so much more 
Alright friends, without further ado, get ready to meet Matthew.
Discover Red Cottage
Connect with Matthew on LinkedIn
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 you’re serious about taking your hospitality brand to the next level, head over to HudsonCreativeStudio.com/behindthestays. Trust me, Eli and his team will make your website something truly special. 
And don’t forget to listen to our series, "Unlocking the Secrets of Successful Hospitality Websites," which we’ll link in the show notes below, for a deep dive into what makes these guys the best in the biz.
Want to book a consulting brainstorm with Zach?
Send him an email directly at zach@staywatch.ai or complete this payment link and get immediate access to his schedule where you can book some time with him!
About the Show
Behind the Stays is brought to you by StayWatch — the internet's best resource for deals on Airbnb, Vrbo, and Booking.com. You can subscribe, for free, at www.staywatch.ai
Behind the Stays is hosted by Zach Busekrus, Co-founder of StayWatch, you can connect with him on Twitter at @zboozee or on LinkedIn. 

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, Paul shares the highs and lows of his entrepreneurial journey, from the struggles of adjusting to city life in the US to the innovative creation of Exclusive Tents — a company that manufactures stunning luxury tents that blend the thrill of outdoor living with high-end comfort, catering to both individual adventurers and world-renowned hospitality brands like Sir Richard Branson’s Virgin.
We’ll dive into the nuances of glamping, the evolution of this unique industry, and the emerging markets that hold exciting potential for luxury outdoor accommodations. Paul’s insights are invaluable for anyone interested in the intersection of nature, innovation, and hospitality.
This episode is brought to you by our friends at Hostfully.
Hostfully Digital Guidebooks are the easiest way to help your guests get to know your property and discover just how special the community that surrounds it is.
Hostfully Guidebooks give you a dynamic place to store every bit of information you might want your guests to have — from the wifi password to how to work the hot tub to where to take the best selfies at golden hour.
Hostfully empowers you with easy-to-use tools that help you feature a totally curated list of your favorite eateries, pubs, hiking trails, and more — OR Hostfully can automatically create a list of experiences through their Guidebook Wizard if you’ve got dozens of properties and just can’t afford to curate a custom set of recommendations for each one.
Learn more here!
Want to book a consulting brainstorm with Zach?
Send him an email directly at zach@staywatch.ai or complete this payment link and get immediate access to his schedule where you can book some time with him!
About the Show
Behind the Stays is brought to you by StayWatch — the internet's best resource for deals on Airbnb, Vrbo, and Booking.com. You can subscribe, for free, at www.staywatch.ai
Behind the Stays is hosted by Zach Busekrus, Co-founder of StayWatch, you can connect with him on Twitter at @zboozee or on LinkedIn. 

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, and kitchen.
In this conversion, Ashley shares her insights on why standardizing these elements can elevate the entire vacation rental experience, drawing parallels to the evolution of the hotel industry.
Discover how Inhaven is partnering with local property managers to implement these standards and ensure that every guest enjoys a reliably excellent stay, no matter where they book.
Ashley also dives into the challenges of scaling a vacation rental management company and why local expertise is crucial for delivering exceptional hospitality. Whether you're a property manager looking to enhance your offerings or a traveler seeking a more predictable vacation rental experience, this episode is packed with valuable insights and innovative ideas.
Tune in to learn how Inhaven is paving the way for a new era in vacation rentals, where comfort and quality are no longer a luxury but a standard.
It’s a tall order, but, if she and the Inhaven team can do it, they’ll be the first company in the space to truly build the Marriott for Vacation Rentals. 
Access the PDF
Connect with Ashley
This episode is brought to you by our friends at Turno. 
Turno is the smartest way to schedule, pay, and find vacation rental cleaners — think of Turno as an Uber or Task Rabbit for STR hosts. 
Simply create an account, describe your listing’s cleaning needs, and Turno will match you with cleaners near you. 
Turno offers simple, affordable pricing for STR hosts of any size. Single property accounts and Marketplace users get access to all the platform’s tools and features for FREE. And they make working with your existing teams easy too, with plans as low as just $6/month per property.
Learn more and earn a $150 Amazon Gift Card after you complete your first cleaning. 
Have you signed up for Ping yet?
Ping makes it easy for guests to be notified when their favorite Airbnbs become available — and it's the secret tool the best Airbnb hosts use to maximize bookings.
Sign up today at bnbping.com
Want to book a consulting brainstorm with Zach?
Send him an email directly at zach@sponstayneous.com or complete this payment link and get immediate access to his schedule where you can book some time with him!
About the Show
Behind the Stays is brought to you by StayWatch. StayWatch brings you the best deals on stays across Airbnb, Vrbo, and Booking.com that align with your travel preferences.
Planning a beach trip for the fam in a couple of months?  Create a Trip on StayWatch and get a curated list of deals that match your criteria sent to you every day.
Perhaps you just want to be notified anytime there’s a great deal on a stay in San Diego, the Blue Ridge Mountains, Bali, or the Texas Hill Country?  Watch a Destination on StayWatch and get the coolest deals on stays that match what you’re looking for every day, every week, or every month!
Oh, and you know that Airbnb you’ve been following on Instagram that’s like always booked?  With StayWatch, you can Follow a Specific Stay and get notified if that stay ever becomes available.
The best part?  It’s all free.
You’ll never overpay for an Airbnb again if you start your search at StayWatch.ai. 
Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.
 

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 preferences.
Planning a beach trip? Create a Trip on StayWatch and get daily curated deals.
Want to be notified about deals in your favorite destinations? Watch a Destination on StayWatch!
Following a specific stay on Instagram that’s always booked? Follow it on StayWatch and get notified when it’s available.
And the best part? It’s all free.You’ll never overpay for an Airbnb again if you start your search at StayWatch.ai
Sign up for the StayWatch for Hosts partner program.