Afleveringen

  • 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 partnerships like Capital One Travel to open new booking channels, and why PR is an essential but often overlooked tool in growing a brand.

    Takeaways include:

    How Rena and her team built a company that balances boutique-style guest service with cutting-edge technology.Why new booking channels like Capital One Travel are game-changers for reaching untapped guest segments.How Boutique’s custom-built revenue management tools give them a competitive edge over off-the-shelf solutions like PriceLabs.Why PR plays a critical role in attracting homeowners, guests, and investors—and how to do it right.Rena’s take on the future of vacation rentals, and where new opportunities lie for entrepreneurs in the space.

    Learn more about Boutiq

    Connect with Rena

    This episode is brought to you by our friends at AirDNA

    Want to see if a Treehouse resort in Dubai pencils? You can do so in AirDNA.

    Want to buy land in Ontario to build a Glamping resort? AirDNA will show you how other, comparable products are performing in the region.

    Or maybe you’ve already got your stay up and running and you want a better understanding of how your Airbnb compares to others in the market? You can connect your listing to AirDNA and get accurate nightly pricing recommendations based on real-world, real-time demand.

    AirDNA is the key you need to unlock the insight behind what it’s going to take to bring those big dreams you have to life.

    Pay just $25/month and access ANY market in the world — AirDNA is cheaper, faster, better, and stronger to use than ever before.

    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.

  • 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 underwriting innovative properties.

    Shari dives into the growing demand for nature-immersive stays, the challenges of securing investment for unconventional assets, and why institutional capital is starting to take notice of this emerging market. She also explores the resurgence of independent hoteliers, driven by a new wave of creative entrepreneurs who are blending luxury, design, and outdoor experiences to redefine hospitality.

    Whether you're a budding hospitality entrepreneur or a seasoned investor, Shari offers invaluable insights into how to build a successful, data-driven strategy in this evolving, exciting, and at sometimes murky space.

    Connect with Shari

    Learn more about Sage Outdoor Advisory

    This episode is brought to you by Enso ConnectMy new friends at Enso Connect have created a tool that’s putting AI to work in a way that’s saving hospitality pros countless hours every week.Here’s how it works: Enso Connect’s Guest Messaging Insights tool dives into your guest messages across all booking platforms. Using AI, it analyzes these interactions and pulls out hidden opportunities that you might be missing.And the best part? It’s FREE, and you’ll get your personalized report in just 72 hours.

    Here’s what this AI-powered report will do for you:

    Analyze your message volume so you can see exactly where your time is going.Break down common guest questions, giving you the info you need to improve your property listings and FAQs.Provide sentiment analysis to understand how guests feel and spot potential issues before they escalate.Offer personalized recommendations that highlight upselling opportunities you might have overlooked, allowing you to tailor your services more effectively.

    Get the report

    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.

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  • 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 offering unforgettable experiences all of which have yielded 95% of their bookings coming direct.

    Finally, Corinne hints at her next big venture—a product line for busy parents on the go. Tune in to hear how Firefly Ridge became a reality, and what’s next for this creative entrepreneur

    Book your stay at Firefly Ridge.

    Follow Firefly Ridge on Instagram

    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.

    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 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 also discuss:

    The importance of integrating technology to automate guest interactions, allowing hosts to focus only on solving real issues like complaints, which in turn lead to happier guests.Francois’ breakdown of upsell opportunities that property managers often leave on the table—like early check-ins, late check-outs, and local experiences—which can generate substantial extra revenue with the right timing and approach.The value of focusing on deep, high-quality integrations with a few key platforms rather than trying to be everywhere at once. And his vision for the future of AI in hospitality,

    This episode is packed with insights for anyone curious about the future of hospitality, from tech-savvy property managers to newcomers looking to scale their vacation rental operations.

    This episode is brought to you by Enso ConnectMy new friends at Enso Connect have created a tool that’s putting AI to work in a way that’s saving hospitality pros countless hours every week.Here’s how it works: Enso Connect’s Guest Messaging Insights tool dives into your guest messages across all booking platforms. Using AI, it analyzes these interactions and pulls out hidden opportunities that you might be missing. And the best part? It’s FREE, and you’ll get your personalized report in just 72 hours.

    Here’s what this AI-powered report will do for you:

    Analyze your message volume so you can see exactly where your time is going.Break down common guest questions, giving you the info you need to improve your property listings and FAQs.Provide sentiment analysis to understand how guests feel and spot potential issues before they escalate.Offer personalized recommendations that highlight upselling opportunities you might have overlooked, allowing you to tailor your services more effectively.

    Get the report

    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 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 in 2024. Discover the lessons he’s learned about resilience, the importance of staying ahead of industry trends, and how his new tool, BNBCalc, is helping others in the industry analyze and scale their own investments.

    Takeaways include:

    How Jeremy transformed a simple idea into a healthy business that allowed him to leave his day jobWhy Jeremy survived when others didn’t, and the secrets to thriving in a post-pandemic market.Why he built BnbCalc The game-changing tool every short-term rental investor needs in their toolkit.How Jeremy is helping others quit their 9-to-5s and achieve financial freedom through short-term rentals.And Jeremy's insights on the current market and why it's ripe for new entrepreneurs.

    Alright friends, without further ado, get ready to meet Jeremy.

    This episode is brought to you by StayFi. StayFi makes it easy to collect data from and market to every single person staying in your short-term rental. StayFi lets you create a custom branded WiFi splash page similar to what you might experience when logging onto the WiFi network at your favorite coffee shop.

    This means you can collect the name, email address, and phone number from every guest staying with you, not just the one who booked
because who doesn’t need to use the WiFi.

    The best part is that once you have their information, you can use StayFi’s email and text marketing tools to keep in touch and make sure they become a guest for life.

    Head on over to StayFi.com and be sure to use the code “BTS” at checkout for 50% off your first 3 months.

    Want to book a consulting brainstorm with Zach?

    Send him an email directly at [email protected] 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 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 scenes of this innovative project, where talented creators Maddie and Will from Guest House Creative hit the road, capturing stunning content across multiple short-term rentals and local businesses.

    Kerri shares invaluable insights on the power of intentionality in partnerships and how aligning with the right creators can elevate your brand without breaking the bank.

    We dive into detail around:

    What the goals of the project areHow all participants in the roadshow — the creators, Kerri, Monique, as well as the incredible entrepreneurs at Lumen Camps and The Maine A-Frames will share and collaborate on content post-campaignWhat the big audience growth strategy of a MAJOR giveaway will look likeIdeas for how other hospitality entrepreneurs might replicate something like this in their own marketAnd so much more

    Follow along on this exciting journey by via the Instagram handles below:

    https://www.instagram.com/will_zimm_/

    https://www.instagram.com/maddie_brandon/

    https://www.instagram.com/guesthousecreativestudio/

    https://www.instagram.com/maineaframe/

    https://www.instagram.com/lumencamps/

    https://www.instagram.com/thevermontaframe/

    https://www.instagram.com/chalets_hygge/

    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 Ree

    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.

  • 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 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.

    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 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 professional success but personal fulfillment and freedom.

    In this episode, Diana takes us through their journey, from the initial struggles of trying to fit into the traditional real estate mold to discovering their true passion for creating unique, wellness-focused boutique hotels. We discuss the challenges they faced, including walking away from two major hotel deals that didn’t align with their vision, and how those experiences ultimately led them to their current project in Palm Springs.

    Diana shares how they’ve leveraged their architectural expertise to add real value to their projects, the lessons they’ve learned in managing properties across three states, and the importance of finding work that truly excites you. This episode is a must-listen for anyone interested in the future of experiential hospitality and the power of aligning your work with your passion.

    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 [email protected] 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.

    Alright friends, without further ado, get ready to meet Diana.

  • 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 challenge into a thriving business that’s changing the game for accessible travel. Some of the biggest misconceptions about what it means to be an accessible short-term rentalThe massive business opportunities that exist in the space for entrepreneurs interested in building with guests that need accessible stays in mindAnd so much more

    Learn more about Becoming RentABLE

    Connect with Lorraine

    Connect with Adam

    This episode is brought to you by StayFi. StayFi makes it easy to collect data from and market to every single person staying in your short-term rental. StayFi lets you create a custom branded WiFi splash page similar to what you might experience when logging onto the WiFi network at your favorite coffee shop.

    This means you can collect the name, email address, and phone number from every guest staying with you, not just the one who booked
because who doesn’t need to use the WiFi.

    The best part is that once you have their information, you can use StayFi’s email and text marketing tools to keep in touch and make sure they become a guest for life.

    Head on over to StayFi.com and be sure to use the code “BTS” at checkout for 50% off your first 3 months.

    Want to book a consulting brainstorm with Zach?

    Send him an email directly at [email protected] 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.

  • 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 OutdoorsBoris & Susan — Lumen Camps Hillary Flur — Folly CollectionMatt Orley — Red Cottage (acquired businesses, memberships, etc.)Brian Meyer — FLOHOMBecca Schulman Havemeyer — Beach PlumJanice Smith — Cozy RockDavid Garber — BrandyWine GroveAmber and Charlie Pledge — KABN Company

    This episode is brought to you by StayFi. StayFi makes it easy to collect data from and market to every single person staying in your short-term rental. StayFi lets you create a custom branded WiFi splash page similar to what you might experience when logging onto the WiFi network at your favorite coffee shop.

    This means you can collect the name, email address, and phone number from every guest staying with you, not just the one who booked
because who doesn’t need to use the WiFi.

    The best part is that once you have their information, you can use StayFi’s email and text marketing tools to keep in touch and make sure they become a guest for life.

    Head on over to StayFi.com and be sure to use the code “BTS” at checkout for 50% off your first 3 months.

    Want to book a consulting brainstorm with Zach?

    Send him an email directly at [email protected] 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 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 inception of Nagel Media Company and its focus on high-quality, authentic content.The misconceptions around influencer marketing and why they choose not to follow the typical influencer path Their vision for creative partnerships in the boutique hospitality sectorTheir unique business model prioritizes the needs of hosts and provides top-tier content without the need for sponsored posts.Future plans for Nagel Media Company, include expansion and a special project dedicated to their roots in the Poconos.

    Get ready to be inspired by Krystal and Eric's innovative approach to content creation and their commitment to maintaining authenticity in the hospitality industry.

    Learn more about Nagel Media Company.

    Follow Krystal and Eric 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 [email protected] 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.

  • 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 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 [email protected] 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 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 incredible journey from serving in the Air Force to becoming a successful hospitality entrepreneur. We explore how his initial investments in real estate and short-term rentals laid the foundation for his entry into the boutique hotel space.

    In this conversation you’ll learn:

    How Blake's early investments and entrepreneurial mindset led him to the boutique hotel industry.The biggest differences between owning and operating short-term rentals and owning and operating boutique hotelsThe massive opportunity that exists to reimagine outdated motels and transform them into boutique hotelsWhy entrepreneurs who’ve figured out how to host well shouldn’t be scared of graduating from STRs to boutique hotelsBlake's views on the emerging trends in hospitality and the advantages of a regional focus for portfolio developmentAnd so much more.

    Follow Blake on Instagram

    Learn more about Boutique Hotel Con

    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 [email protected] 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 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 [email protected] 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 [email protected] 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 yearsThe 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 PostoThe importance of maintaining brand authenticity while scalingThe 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 [email protected] 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 [email protected] 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 [email protected] 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.

  • 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 it, he sold it again to HomeAway. He then turned his attention to vacation rental management, co-founding TurnKey Vacation Rentals, which he successfully sold to Vacasa in 2021.

    Today, Eric is at the helm of BNB Finder, a no-fee booking platform for professionally managed properties, aimed at providing travelers with a seamless booking experience and property managers with greater control over their listings.

    In our conversation, Eric shares:

    The challenges and triumphs of convincing innkeepers to embrace the internet in the early days of bedandbreakfast.com.His experiences in scaling and selling multiple businesses in the travel sector.Insights into the evolving vacation rental market and the importance of professional management.The innovative model of BNB Finder and its potential to disrupt the industry by eliminating booking fees.

    Discover BnBFinder

    Connect with Eric 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 [email protected] 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 twice a week by Sponstayneous — a free, biweekly newsletter that brings subscribers the best last-minute deals and upcoming steals on Airbnb.

    You can subscribe, for free, at www.sponstayneous.com.

    Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.