SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips

By: Airbnb Superhost Jason Muth + Rory Gill
Listen for free

  • Summary

  • Welcome to the SmartStay Show, your go-to podcast for mastering Short-Term Rentals on Airbnb, Vrbo, and beyond. For more Airbnb tips, visit smartstayshow.com and smartstaycoaching.com. Hosted by 30-time Airbnb Superhost Jason Muth and Real Estate Attorney Rory Gill, we equip you with the tools to launch, manage, and optimize your vacation rental like a pro. Unlike other shows, we specifically cater to owners of small-but-mighty portfolios who self-manage their properties. Each episode delivers expert insights, legal tips, and proven strategies from successful hosts across the U.S. Whether you’re buying your first property, improving your listing, or looking to stay ahead of the competition, we offer actionable advice and real-life stories to help you thrive. From pricing strategies to guest communication, we provide the playbook to turn your property into a top-performing rental. Subscribe now and unlock your rental’s full potential with the SmartStay Show!
    © 2024 SmartStay Show
    Show More Show Less
Economics Leadership Marketing Personal Finance
Show More Show Less
Episodes
  • Our $130k Flood Claim - How Proper Insurance Saved Our STR Lake Home! | Darren Pettyjohn

    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!
    Show More Show Less
    42 mins
  • NEVER Overlook This in Your Airbnb Design (Insider Tips) | Dre Shapiro

    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!
    Show More Show Less
    37 mins
  • How BiggerPockets’ STR Expert Stays Fully Booked Year-Round | Garrett Brown

    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!
    Show More Show Less
    48 mins

What listeners say about SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips

Average customer ratings

Reviews - Please select the tabs below to change the source of reviews.

Audible.co.uk reviews

Amazon reviews
No Reviews are Available