Behind the Stays

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 Connect My 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 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 Connect My 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 job Why 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 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 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 are How 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-campaign What the big audience growth strategy of a MAJOR giveaway will look like Ideas for how other hospitality entrepreneurs might replicate something like this in their own market And 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 Reel Live Oak Lake Reel FLOHOM Reel Villa 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 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.  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 rental The massive business opportunities that exist in the space for entrepreneurs interested in building with guests that need accessible stays in mind And 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 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. 

In this discussion, a group of ten groundbreaking entrepreneurs share their insights into the future of hospitality. Justin Potts promotes lifestyle through creative media, while Sara Roitman and Nick Purslow craft unique outdoor experiences. Boris and Susan specialize in immersive camping, alongside Hillary Flur's luxurious travel ventures. Matt Orley and Brian Meyer revolutionize the cottage and home services industry. Plus, Becca Schulman Havemeyer and Janice Smith offer cozy coastal and outdoor experiences. David Garber adds a touch of wine, while Amber and Charlie Pl. adventure in hospitality!