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

By: Airbnb Superhost Jason Muth + Rory Gill
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  • 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
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Episodes
  • How to Handle Airbnb Guests + Issues Without Being On-Site | Jarrett Chouinard

    How to Handle Airbnb Guests + Issues Without Being On-Site | Jarrett Chouinard
    Nov 21 2024
    In this episode, I’m joined by Jarrett Chouinard, the founder of Stellar Retreats, who shares his inspiring journey into the short-term rental world. Starting with just one arbitrage unit in Connecticut, Jarrett has grown his business into a thriving operation spanning multiple properties in New York, Rhode Island, and beyond. We’ll dive into his experiences with the challenges of the arbitrage model, how he navigates working with landlords, and the lessons he’s learned about guest demographics and client relationships. Jarrett also shares his approach to technology, systems, and building a team that supports growth. And as if that’s not enough, we’ll also talk about Jarrett's ambitious plans for the future and his entrepreneurial ideas that go beyond short-term rentals. This is a must-listen for anyone looking to learn, grow, and succeed in the short-term rental industry. Let’s get started! Things we discussed in this episode: Jarrett's transition from media and advertising into short-term rentals and real estate. The challenges and risks of the Airbnb arbitrage model, including dealing with landlords. The differences in guest demographics and communication styles across Jarrett's properties in different locations. Jarrett's approach to saying no to potential clients who don't fit his standards and the importance of working with the right partners. The technology and systems Jarrett uses, including smart locks, cameras, property management software, and supply delivery. Jarrett's plans to expand Stellar Retreats to 15 clients by the end of the year and his interest in other entrepreneurial ventures. The value of building a reliable ground team and the challenges of managing properties remotely. The benefits of hosting a short-term rental meetup in New York City to build a local network and community. The lessons Jarrett wishes he had known when starting, including the importance of not being intimidated by challenges. The role of trial and error, making mistakes, and learning in growing a successful short-term rental business. Get in touch with Jarrett: Facebook - https://www.facebook.com/jarrett.chouinard Instagram - https://www.instagram.com/jarrettchouinard/ Website - https://www.stellaretreats.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #AirbnbArbitrage #PropertyManagement #EntrepreneurialMindset #HospitalityTechnology #RemoteTeamBuilding #CommunityBuilding #GuestExperience #ScalingSTRBusiness #HospitalityInsights 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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    40 mins
  • Say Goodbye to Strangers Renting Your Second Home | Brent Hieggelke

    Say Goodbye to Strangers Renting Your Second Home | Brent Hieggelke
    Nov 19 2024
    In this episode, we’re thrilled to sit down with Brent Hieggelke, the visionary founder of Trustr, a groundbreaking platform redefining the short-term rental experience. Brent brings decades of experience in the vacation rental world, and together, we dive into how Trustr taps into the power of social networks to create trusted, more personal guest-host connections. Say goodbye to renting to total strangers and hello to curated "guest lists" of friends, family, and acquaintances! We explore how this innovative model leverages word-of-mouth recommendations, integrates with property management tools, and even uses an affiliate-style approach to enhance platforms like Airbnb and VRBO. Whether you're a property owner hesitant to list or a guest seeking more authentic stays, this episode is packed with insights into the future of short-term rentals. Tune in now to hear how Truster is bridging the gap and opening new doors! Things we discussed in this episode: Truster's mission to enable more trusted short-term rental experiences by leveraging people's existing social networks. The hesitation some property owners have about renting to complete strangers, and Truster's solution of curated "guest lists." The power of word-of-mouth and personal recommendations over generic online reviews. Truster's plans to integrate with property management software and leverage an affiliate-style model. The challenges of convincing some owners to list their properties, especially if they view them as personal retreats. Brent's personal experiences navigating the vacation rental industry as a property owner. The evolution of the short-term rental market and the potential for platforms like Truster to unlock new opportunities. The concept of "serendipitous" property recommendations through social media and community groups. Truster's approach to offering different levels of privacy for property listings, from completely private to public. The idea of Truster serving as a "pipeline builder" for larger vacation rental platforms like Airbnb and VRBO. Get in touch with Brent: Facebook - https://www.facebook.com/brenth Instagram - https://www.instagram.com/bhieggelke/ Website - https://trustr.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #TrustedConnections #SocialNetworkRentals #PersonalizedHospitality #VacationRentalInnovation #PropertyOwnerEmpowerment #WordOfMouthMarketing #RentalMarketDisruption #TrustedRecommendations #CuratedGuestExperience 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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    34 mins
  • Land High-Quality Content Creators for Your Rentals (Step-by-Step) | Jordan Kahana

    Land High-Quality Content Creators for Your Rentals (Step-by-Step) | Jordan Kahana
    Nov 14 2024
    In this episode, we explore the intersection of travel, content creation, and short-term rental marketing with special guest Jordan Kahana, founder of Stayamo. As the lines between work and vacation blur, today’s creators are reimagining how destinations are experienced and showcased. Jordan explains how Stayamo connects properties with creators, making it easier for hosts to collaborate with storytellers and bring their spaces to life. Host Jason Muth, a 29-time Airbnb Superhost, has firsthand experience listing his property on Stayamo, with results that speak for themselves. Joined by real estate broker Rory Gill, they discuss the shift from traditional real estate photography to lifestyle-driven visuals that capture what it’s really like to stay at a property. From staging seasonal scenes to negotiating with creators, Jordan shares top strategies for short-term rental owners. Whether you’re a host wanting to enhance your marketing or a content creator looking for new opportunities, this episode is packed with insights. Don’t miss it! Things we discussed in this episode: The blurred lines between work and travel for content creators How content creators are changing the way unique destinations are marketed The difference between "influencers" and "content creators" The founding story and purpose behind the Stay AMO platform The types of properties that benefit most from content creator partnerships The evolution of real estate photography vs. lifestyle photography for short-term rentals Best practices for property owners when working with content creators Negotiating the scope of deliverables and duration of stays with creators The long-term value of building a content library for property owners The incentives and benefits for content creators to collaborate on the Stayamo platform Get in touch with Jordan: Website - https://stayamo.com/ Instagram - https://www.instagram.com/jordankahana Youtube - https://www.youtube.com/@JordanKahana/videos #SmartStayShow #realestate #realestateinvesting #realestateinvestor #RealEstateEntrepreneur #remotework #digitalnomad #travelinfluencer #stayation #vacationrental #airbnb #shorttermrental #visualstorytelling #dronephotography #influencermarketing Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for another episode of The Real Estate Law Podcast! Following and subscribing to The Real Estate Law Podcast 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. The Real Estate Law Podcast 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 This podcast and these show notes are not legal advice, but we hope you find both entertaining and informative. Hospitality.FM The Real Estate Law Podcast 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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    33 mins

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