• Our $130k Flood Claim - How Proper Insurance Saved Our STR Lake Home! | Darren Pettyjohn
    Jan 14 2025
    Ever Dealt With a Flooded Rental Property? This Could Save You Thousands. As short-term rental owners, Rory and I have seen it all - from the good, the bad, to the downright disastrous. One fateful night, we got that dreaded 2am call about a flooded property, and let me tell you, it was a nightmare. But what happened next is the real story. In this episode, we sit down with Darren Pettyjohn, the co-founder of Proper Insurance, to unpack why short-term rental insurance is so crucial - and how their specialized coverage saved our bacon when disaster struck. Darren pulls back the curtain on the unique challenges facing vacation rental owners, the sneaky tricks some insurance companies use, and the innovative solutions Proper has pioneered. If you own a short-term rental property, or are thinking about getting into the game, you won't want to miss this. It could be the difference between a minor headache and a total nightmare. Click play and find out how Proper Insurance can give you the peace of mind to focus on being a 5-star host. Things we discussed in this episode: Flood Nightmare and Insurance Savior - Jason and Rory's experience with a flooded short-term rental property and how Proper Insurance stepped in to help. Specialized Insurance Policies - The need for niche insurance products tailored to specific industries like short-term rentals. Proper Insurance's Unique Features - Endorsements like bed bug coverage, squatters insurance, and no limit on guest-caused damage. In-House Claims Administration - Proper Insurance's ability to control the claims process from start to finish, leading to better customer service. Differences Between Short-Term Rental and Standard Homeowner's Policies - The multi-use nature of short-term rentals and the need for a combined homeowner's, landlord, and commercial policy. Positive Claims Experience - Jason and Rory's praise for Proper Insurance's transparent communication and their ability to make the claims process smooth. Risks of Misrepresentation - The potential consequences of homeowners misrepresenting the use of their properties to insurance companies. Worcester Insurance - Proper's sister company providing business policies for professional property managers. Wave O - Proper's guest damage protection solution, offering an alternative to traditional security deposits. Importance of Employee Engagement - Darren's insights on the challenges of managing a growing business and the value of maintaining personal connections with employees. Get in touch with DARREN: Facebook - https://www.facebook.com/propervacationrentalinsurance Instagram - https://www.instagram.com/properinsurance/ Website - https://www.proper.insure/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #ShortTermRentalInsurance #PropertyProtection #ClaimsManagement #VacationRentalOwners #RiskManagement #PropertyManagerInsurance #GuestDamageProtection #EntrepreneurialInsights #InsuranceInnovation #PeaceOfMind Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    42 mins
  • NEVER Overlook This in Your Airbnb Design (Insider Tips) | Dre Shapiro
    Jan 7 2025
    What happens when a passion for design meets the wild beauty of Joshua Tree? In this episode, Rory Gill and I sit down with Dre Shapiro, a designer whose journey into short-term rentals is as inspiring as it is unexpected. Dre fell in love with a vacation rental in Joshua Tree, turned it into her own, and transformed it into a guest favorite through her incredible design sensibilities. We discuss her unique approach to creating unforgettable guest experiences, from curated book collections and vintage record players to custom murals and luxurious amenities. Dre’s story showcases how personal touches can set your rental apart. Operating in the desert isn’t without its challenges. Dre opens up about staffing hurdles, maintenance struggles, and how showing appreciation to her team has been a game-changer. Plus, she shares practical tips for new hosts on blending thoughtful design with minimalist comfort, helping guests feel at home while standing out in the market. This episode is packed with insights, laughs, and lessons for anyone in—or considering joining—the short-term rental space. Whether you’re a host, a guest, or simply love design, you won’t want to miss it! 🎧 Things we discussed in this episode: Dre Shapiro's unique journey of falling in love with a vacation rental and purchasing the property in Joshua Tree. Dre's design expertise and attention to detail in creating a welcoming and memorable guest experience. The influence of Dre's New York background and how it shapes her design approach and business mindset. The challenges of operating short-term rentals in the harsh desert environment of Joshua Tree, including staffing issues and constant maintenance needs. Dre's emphasis on treating her team well, offering bonuses and praise to maintain loyalty and ensure high-quality service. The importance of providing guests with thoughtful touches, such as curated book collections, vintage record players, and custom-designed elements. The competitive nature of the short-term rental market in Joshua Tree and the need for continuous improvement and guest experience enhancement. Dre's process of de-personalizing her primary residence for short-term rentals and the role of property managers in preparing the space. Dre's advice for new short-term rental owners, highlighting the importance of clean, minimalist design with character and charm. The value of providing guests with useful recommendations and information about the local area to enhance their overall experience. Get in touch with Dre: Email - DRE@dredesign.co Instagram - https://www.instagram.com/dre_design_/ Website - https://www.dredesign.co/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #AirbnbDesign #JoshuaTreeRentals #HostingTips #GuestExperience #DesertDesign #NewYorkInfluence #PropertyManagement #CreativeHosts #HospitalityDesign Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    37 mins
  • How BiggerPockets’ STR Expert Stays Fully Booked Year-Round | Garrett Brown
    Jan 2 2025
    Ready to learn from one of the top short-term rental experts in the game? In this episode of the Smart Stay Show, we’re joined by Garrett Brown, the resident expert at Bigger Pockets, who shares his journey from hospitality to real estate success. Garrett reveals how his background in hotels and restaurants shaped his approach to managing multiple short-term rentals. He also talks about the importance of staying positive, adapting quickly, and creating consistent content—even when it doesn’t yield instant results. Looking for tips on managing properties or discovering the next big short-term rental trend? Garrett has it covered. From finding rising hot spots to offering unique guest experiences, this episode is packed with valuable insights for anyone in the STR world. Things we discussed in this episode: Garrett Brown's background in hospitality and hotel/restaurant management Garrett's journey of discovering Bigger Pockets and how it sparked his real estate investing Garrett's role as the resident short-term rental expert at Bigger Pockets The launch of Garrett's Bigger Stays newsletter The importance of not dwelling on small issues and accepting that not everyone will be pleased Garrett's experience attending Bigger Pockets Con and the unexpected hurricane The value of building credibility through consistent content creation Garrett's strategies for managing short-term rentals, including well-trained teams and processes Garrett's approach to attracting co-hosting opportunities through his content Garrett's prediction of the rise of "rising hot spots" as the next big short-term rental trend Get in touch with Garrett: Tiktok- https://www.tiktok.com/@garrettbrownre Instagram - https://www.instagram.com/garrettbrownre/# Website - https://www.biggerpockets.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #AirbnbHosting #HospitalityIndustry #RealEstateInvesting #BiggerPockets #ContentCreation #GuestExperience #SystemsAndProcesses #RisingHotSpots #ShortTermRentalTrends Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    48 mins
  • The Genius Solution for Family-Friendly Airbnbs (No Gear Required!) | BabyQuip CEO Fran Maier
    Dec 30 2024
    Ever wondered how to transform your short-term rental into a family-friendly haven? In the latest episode of the Smart Stay Show, Rory and I sit down with Fran Maier, CEO of Baby Quip, to explore how providing essential baby and toddler gear can elevate the guest experience. Fran shares her journey as a host-turned-innovator and how Baby Quip helps families travel light while ensuring hosts deliver a seamless stay. From reducing guest packing stress to offering promo codes and affiliate opportunities, this episode is packed with insights you won’t want to miss. Plus, hear firsthand how Rory and I tackled the chaos of traveling with a little one! Tune in now and discover how small changes can make a BIG impact. Don't miss Fran’s exclusive 20% promo code—perfect for your next family-friendly hosting upgrade. Things we discussed in this episode: Packing and transporting baby/toddler gear for family travel Hosts equipping their vacation rentals for families with young children Fran Meyer's experience as an early Airbnb host in San Francisco Fran's journey of starting and growing Baby Quip The benefits of having a local provider deliver and set up gear for guests Hosts earning affiliate fees by recommending Baby Quip to guests Expanding Baby Quip's services to include pet and beach gear The sustainability aspect of renting versus buying new baby equipment Regulatory challenges impacting short-term rental hosts The importance of hosts focusing on what they enjoy about the business Get in touch with Fran: Email - https://www.facebook.com/BabyQuip/ Instagram - https://www.instagram.com/babyquip/ Website - https://www.babyquip.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #VacationRentals #FamilyTravel #BabyGear #ShortTermRentals #GuestExperience #HospitalityInnovation #StartupStory #AirbnbHost #SustainableTravel #PassiveIncome Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    31 mins
  • The Truth About Direct Bookings for Serious Airbnb Hosts | Abby Grous
    Dec 23 2024
    What if you could reduce your reliance on OTAs, save money, and build a loyal guest base—all while maintaining complete control over your short-term rental business? That’s exactly what we’re exploring in this episode of The SmartStay Show! Rory Gill and I sit down with Abby Grous, the Senior Product Manager of Direct at Hospitable, to unpack the power of direct bookings. From Hospitable’s innovative tools to real-world strategies for maximizing revenue, we cover everything you need to know about making direct bookings work for you. Abby gives us an inside look at Hospitable’s basic and premium offerings, shares tips for boosting guest loyalty, and highlights the game-changing features on their product roadmap. This is your chance to learn how to optimize your direct booking process, enhance the guest experience, and take full ownership of your rental business. Don’t miss the special referral code Abby shares exclusively for our listeners—your next step to hosting success starts here. Things we discussed in this episode: The importance of direct bookings for short-term rental hosts and the benefits of having control over the guest experience. Hospitable's two direct booking product offerings - the basic and premium options - and the differences between them. The integration of Hospitable's direct booking tools, including the direct booking landing pages, widgets, and payment processing. The ability to manage taxes, discounts, and promo codes through Hospitable's direct booking platform. The challenges of integrating guest reviews on direct booking websites and Hospitable's plans to address this. Strategies for increasing direct bookings, such as capturing guest email addresses, utilizing social media, and offering trust-building content. Hospitable's focus on improving the booking flow, including features like express checkout for returning guests and skipping guest verification. Hospitable's partnership with Auto Host for guest vetting and the importance of this process for providing damage protection. Hospitable's plans to expand into the midterm rental market, including offering monthly payment options and alternative payment methods. Hospitable's commitment to building in partnership with their customers and the role of customer feedback in shaping the product roadmap. Get in touch with Abby: Facebook - https://www.facebook.com/hospitable/ Instagram - https://www.instagram.com/hospitable_com/ Website - https://hospitable.com/contact-us/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #DirectBookings #PropertyManagement #GuestExperience #PaymentProcessing #ReviewManagement #GuestVetting #DamageProtection #HospitableDirectBooking #STRHostTips Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    43 mins
  • Remote Hosting Secrets Every Airbnb Host Should Know! | Punith Upadhya
    Dec 17 2024
    Ready to take your short-term rental business to the next level? In this episode of the Smart Stay Podcast, Rory Gill and I chat with Punith Upadhya, the mastermind CEO of Moon Gaze Stays, who’s figured out how to run a world-class short-term rental operation from hundreds of miles away! Puneet pulls back the curtain on his game-changing strategies, including how he’s built seamless systems, empowered his local team, and mastered the art of delivering unforgettable guest experiences. Plus, he reveals how the "Limitless" program transformed his mindset, helping him tackle challenges and seize unexpected opportunities with confidence. We also get into his personal tips for staying motivated, creating SOPs that keep operations smooth, and adding those wow-factor touches that guests rave about. If you’re serious about scaling your short-term rental business and learning from a true pro, this is the episode you can’t miss. Hit play and get inspired! Things we discussed in this episode: Managing short-term rentals remotely and delivering a world-class guest experience The role of gratitude, strategy, and luck in the short-term rental industry Puneet's "Limitless Mindset" and how it has shaped his approach to business The importance of creating SOPs and systems to ensure consistent service Puneet's use of personalized touches, like welcome gifts and customized guidebooks, to enhance the guest experience The strategy behind Puneet's direct booking efforts and capturing guest information The value of having a business partner with complementary skills and expertise The challenges and benefits of delegating tasks and focusing on high-value activities Puneet's strategies for staying motivated during tough times, including changing environments and reconnecting with goals Puneet's background in engineering and how it has influenced his approach to short-term rental management Get in touch with Punith: Facebook - https://www.facebook.com/punith.upadhya Instagram - https://www.instagram.com/punith3upadhya/ Website - https://www.moongazestays.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #RemoteManagement #GuestExperience #LimitlessMindset #SystemsAndProcesses #PersonalizedTouches #DirectBookings #BusinessPartnerships #Motivation #EngineeringApproach Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    48 mins
  • Airbnb Guests Are Paying MORE for Vintage + Local Vibes - Here’s Why! | Christina Melander
    Dec 10 2024
    In this episode of the Smart Stay Show, I sit down with Christina Melander, the founder of Knotty Pine Design and a talented short-term rental host, to discuss how she creates memorable guest experiences with a blend of budget-conscious, authentic design. Christina shares her insights on crafting distinctive, fantasy-driven vibes that stand out on listings and leave a lasting impression. We dive into how to balance sturdy, long-lasting furniture with unique, locally-sourced pieces, and how meaningful items like family heirlooms and artwork can elevate the guest experience. Christina also shares practical advice for new hosts, including sourcing high-quality furnishings through resale channels, gathering guest feedback, and avoiding generic décor. If you're a short-term rental host looking to elevate your space and make a real impact on your guests, this episode is full of valuable takeaways. Tune in for inspiration on creating a home away from home that your guests will never forget! Things we discussed in this episode: Christina's superpower is her ability to create authentic, lived-in spaces through her eclectic, budget-conscious design approach. Incorporating local, vintage, and one-of-a-kind items to create a distinctive guest experience. Displaying meaningful items and furnishings, while trusting guests to respect the care and thought put into the rental. Balancing automated messages with personalized touchpoints to maintain a high level of guest satisfaction. The benefits of sourcing furnishings through resale channels to reduce packaging waste and support the circular economy. Investing in high-quality, long-lasting items that can withstand the wear and tear of short-term rentals. Gathering input from early guests to continuously improve the rental experience. Avoiding cast-off furniture and generic art - Advice for new hosts to create a cohesive, welcoming environment. The importance of providing coasters to prevent water damage in humid environments. Christina's design firm specializes in creating unique, budget-conscious spaces for short-term rentals. Get in touch with Christina: Email - cm@knottypine.design Instagram - https://www.instagram.com/knottypine.design/ Website - https://www.knottypine.design/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #AirbnbHosting #UniqueDesign #BudgetFriendlyDecor #SustainableHospitality #GuestExperience #VintageFinds #LocalTouchpoints #HostCommunication #InteriorDesignTips Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    38 mins
  • How Proper Signage Can SAVE Your Airbnb from Bad Reviews | Jason Muth + Rory Gill
    Dec 5 2024
    In this episode of The Smart Stay Show, we’re diving into the critical role of signage in short-term rentals. From the must-have Wi-Fi sign to rules about smoking, plumbing, and pets, this episode is packed with practical advice to help you create a seamless guest experience. We’ll discuss how to balance necessary information with tasteful design, avoid the pitfalls of overwhelming guests, and even incorporate humor and creativity to make your signs stand out. Tune in for actionable tips to protect your property, keep guests informed, and enhance their stay! Things discussed in this episode: Importance of signage in short-term rentals to reduce guest questions and enhance the guest experience. Wi-Fi information signs, including network name and password or login instructions. Smoking rules signs, indicating whether smoking is allowed indoors, on the premises, or not at all. Signs reminding guests not to flush anything except toilet paper, to prevent plumbing issues. Signs for pet-friendly properties, requesting guests keep pets off beds and furniture. Thermostat instruction signs to prevent guest confusion and HVAC system damage. QR codes linking to an interactive guest guide for easy access to property information. Incorporating humor and artistic flair into sign design to make them more appealing to guests. Signs for outdoor amenities like hot tubs, fire pits, and fireplaces to ensure proper usage. Signs for specialized features like butcher block countertops, providing care instructions. Get in touch with Jason: Facebook - https://www.facebook.com/jasonmuth Linkedin - https://www.linkedin.com/in/jasonmuth/ Website - https://www.smartstayshow.com/ https://www.straightforwardstrs.com/ https://prideawaystays.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbHostTips #ShortTermRentalSignage #GuestExperienceEnhancement #PlumbingProtection #PetFriendlyRules #ThermostatInstructions #QRCodeGuides #CreativeSignDesign #IdiotProofingYourRental #ShortTermRentalHacks Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for another episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. ***** SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn SmartStay Coaching Website and on Instagram Straightforward Short-Term Rentals Website Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn ***** This podcast and these show notes are not legal advice, but we hope you find both entertaining and informative. Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    17 mins