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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 - [email protected]
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
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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! -
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
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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! -
Saknas det avsnitt?
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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! -
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! -
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! -
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 - [email protected]
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! -
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! -
In this episode, we’re joined by the brilliant Justin Miller, co-founder of Showplace and a true trailblazer in hospitality design. Justin brings a wealth of experience to the table, having co-founded Pillow, a groundbreaking property management tech platform, and now leading Showplace, where he helps rental owners and investors create spaces that leave a lasting impression.
Justin’s journey is as inspiring as it is insightful. From navigating the challenges of launching tech-driven solutions for property management to becoming a go-to expert for design-driven short-term rental setups, he’s seen firsthand how the right approach can elevate a property from ordinary to extraordinary. Whether you’re new to hosting or a seasoned STR owner looking for fresh ideas, Justin’s advice is packed with actionable insights you can start using today. Tune in now and discover how the power of design can help you create a short-term rental that guests will never forget!
Things we discussed in this episode:
The importance of setting up a short-term rental property for success before the first guest arrives
The concept of the "amenities arms race" and the need for high standards in short-term rentals
The significance of the first 5 photos in a short-term rental listing and how they can impact bookings
The differences between designing a primary residence versus a short-term rental property
The value of incorporating local flavor and branding into short-term rental design
Showplace's comprehensive design process, including mood boards and product lists
Tips for DIY hosts, such as using group purchasing organizations and local storage units
The importance of understanding both the real estate and hospitality aspects of short-term rentals
Practical setup tips, like using roll-off dumpsters and white-glove delivery services
Justin Miller's plans to launch a new podcast called "Showplace" in Q4 2024
Get in touch with Justin:
Facebook - https://www.facebook.com/showplacehq
Instagram - https://www.instagram.com/showplace_hq/
Website - https://www.showplacehq.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #ShortTermRentalDesign #AirbnbInteriorDesign #VacationRentalOptimization #GuestExperienceDesign #HospitalityInvestments #InstagrammableSpaces #AmenitiesArmsRace #RealEstateHospitalityConvergence #MemorableTravelExperiences #DesignForProfitability
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! -
In this episode, We dive into the crucial role of location in short-term rental success. From being close to key attractions like beaches and national parks to considering the charm of quieter residential neighborhoods, I’ll walk you through the factors that can make or break your rental’s performance.
I also share my experiences hosting in Provincetown, Massachusetts, and offer practical tips for enhancing the value of your property—whether it's upgrading amenities, marketing hidden gems in your area, or catering to your guests' specific needs. Tune in to learn how to unlock the full potential of your short-term rental through the power of location!
Things discussed in this episode:
The importance of location in short-term rentals and how it can impact rental performance.
How location affects the value and rental rates of properties, particularly lakefront and beachfront properties.
The benefits and potential drawbacks of being in prime locations, such as near beaches or lakes.
Considerations for choosing the right location when purchasing a new short-term rental property.
The impact of neighborhood and community culture on the success of short-term rentals.
Strategies for promoting lesser-known local attractions and unique features of an area.
The importance of upgrading the property's own amenities and experiences to enhance the guest experience.
The use of great photography and accurate marketing to highlight a property's location and proximity to attractions.
Understanding the target market and catering to their specific needs and preferences.
Leveraging a property's proximity to popular destinations by positioning it as a "base camp" for day trips and activities.
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 #AirbnbSuperhost #ShortTermRentalSuccess #ShortTermRentals #LocationMatters #AirbnbHosting #PropertyInvesting #VacationRentals #CommunityDynamics #GuestExperience #MarketingTips #TargetMarket #DestinationTravel
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! -
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! -
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! -
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! -
Ever wondered what it’s like to live in a house full of entrepreneurs all driven to succeed? Meet Jesse Ray, the mind behind the "Growth House" concept, where like-minded professionals live, learn, and grow together under one roof. In this episode, Jesse Ray shares his journey from corporate America to real estate investing and the game-changing decision that sparked his success: building a community that fuels ambition.From shared masterclasses to daily accountability, the Growth House isn’t just a place to live; it’s a place to thrive. Jesse explains how residents like Derek went from managing a few properties to scaling up to 60+ rentals, all thanks to the connections and support within the house.Join us as we dive into the power of intentional living, the importance of community, and how surrounding yourself with the right people can ignite your path to success. Whether you’re an entrepreneur or just curious about real estate innovation, this episode has something for you. Don’t miss it!Things we discussed in this episode:The origin and concept behind the Growth House modelJesse's transition from corporate America to real estate investing and entrepreneurshipThe importance of surrounding yourself with like-minded, growth-oriented individualsThe Harvard study on the impact of the 5 people you surround yourself withJesse's experience of moving out of his hometown in his 20s to pursue entrepreneurial opportunitiesThe challenge of adult loneliness and the need for in-person connectionsJesse's vetting process for selecting Growth House residentsThe evolution of the Growth House model, including the potential for a cohort-based programMonetization strategies for the Growth House, such as rent, sponsorships, and a potential investment fundThe power of proximity and its impact on mindset, belief, and successGet in touch with Jesse:Facebook - https://www.facebook.com/profile.php?id=100010717680041Instagram - https://www.instagram.com/_thegrowthhouse/Podcast - https://podcasts.apple.com/us/podcast/journey-from-%240-to-%2410-million-business-solo-jesse-ray-37/id1713820406?i=1000648515810#realestatepodcast #realestate #realestateinvestor #realestatelaw #realestateagent #RealEstateInvesting #Entrepreneurship #CoLiving #BusinessCommunity #PassiveIncome #StartupGrowth #MindsetShift #CorporateExit #Resilience #EntrepreneurialJourney*****Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for another episode of SmartStay Show!*****SmartStay Show Website and on Instagram and YouTubePrideaway Stays Website and on Facebook and LinkedInSmartStay Coaching Website and on InstagramStraightforward Short-Term Rentals WebsiteAttorney Rory Gill on LinkedInJason Muth on LinkedIn*****This podcast and these show notes are not legal advice, but we hope you find both entertaining and informative.Hospitality.FMSmartStay 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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Have you ever wondered if the skills you’ve developed in your day job could translate into a thriving business? Meet Mike Stone—a former corporate attorney who transformed his career, channeling his expertise into building a successful short- and medium-term rental empire. Mike’s journey began with an ambitious leap from the legal world into vacation rentals, and his success speaks to the power of leveraging industry insights in new ways.
In this episode, Mike opens up about his pivot from attorney to rental entrepreneur, sharing how he secures high-yield, mid-term bookings by targeting insurance companies rather than traditional vacation renters. He provides insider tips on navigating the rental space, detailing his experience with Airbnb arbitrage—a venture that proved costly but ultimately led him to a co-hosting model he’s convinced is far more sustainable and profitable. Tune in as Mike reveals essential strategies for building credibility, tapping into your network, and finding unique opportunities in the rental industry, including landing a $12,000/month contract for a 12,000-square-foot property. Whether you’re curious about the transition into real estate or looking to expand your rental business, Mike’s story offers invaluable lessons and inspiration!
Things we discussed in this episode:
Mike Stone's transition from corporate attorney to short-term rental entrepreneur
His experience with Airbnb arbitrage, including a costly failed deal
The benefits of co-hosting over arbitrage, including equity, appreciation, and tax advantages
Pro tips for mitigating risk in arbitrage deals
The importance of leveraging group reputation to secure initial co-hosting opportunities
Mike's recent success in securing a $12,000/month contract for a 12,000 sq ft home
The process of building relationships with insurance companies for medium-term rentals
The negotiation dynamics when working with insurance companies vs. individual renters
Strategies for targeting medium-term rentals during short-term rental slow seasons
The value of asking for higher prices and not accepting lower offers from individual renters
Get in touch with Mike:
Website -https://www.strignite.com / https://allstr.com
Linkedin - https://www.linkedin.com/in/mike-stone-5a303b31/
Facebook - https://www.facebook.com/mstone219/about
#SmartStayShow #realestate #realestateinvesting #realestateinvestor #realestatelaw #realestateagent #socialmedia #realestatemarketing #ShortTermRentals #MediumTermRentals #Airbnb #RealEstateInvesting #PropertyManagement #CareerChange #PersonalDevelopment #InsuranceCompanies #Masterminds #EntrepreneurLife
*****
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! -
Today, we're thrilled to welcome Andrew Rodriguez, the co-owner of Stay Booked, a full-service short-term rental management company. Andrew and his wife, Lindsay, have built an impressive portfolio of larger, unique vacation homes in sought-after destinations like the Poconos.
What sets Andrew and his team apart is their unwavering commitment to quality over quantity. From the moment a guest lays eyes on one of their properties to the second they check out, Andrew and his crew strive to deliver an exceptional experience.
With a background in sales and a keen eye for detail, Andrew has developed a unique approach to short-term rental management that has earned him a loyal following. He's here today to share his insights on building a successful STR business, navigating the challenges of managing larger properties, and fostering a strong sense of community within the industry.
So, let's dive in and learn from Andrew's wealth of knowledge and experience.
Things we discussed in this episode:
Andrew Rodriguez's emphasis on "quality over quantity" in his short-term rental business
The story of how Andrew and his wife Lindsay got into the short-term rental industry
Their use of FHA and second home loans to acquire properties, including a 6-bedroom cabin in the Poconos
The importance of professional design and attention to detail in their properties
The challenges of managing larger short-term rental properties, including the need for a trusted "runner"
Strategies for handling guest feedback, both positive and negative
The evolving expectations of short-term rental guests and the value of empathy
The role of community and networking within the short-term rental industry
Andrew's belief that anyone can achieve their short-term rental dreams with dedication
The meetup group Andrew and a fellow mastermind member started in New York City
Get in touch with Andrew:
Facebook - https://www.facebook.com/profile.php?id=61552248421123
Linkedin - https://www.instagram.com/yourstaybooked/
Website - https://www.stay-booked.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #VacationRentals #GuestExperience #PropertyManagement #EntrepreneurLife #CommunityBuilding #HospitalityIndustry #SuccessStories
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! -
In today’s episode, I’m excited to introduce you to a truly inspiring figure in the vacation rental industry, Rose Tipka. Rose isn't just a successful short-term rental host; she's a homeschooling mom of six who's managed to build a multi-million-dollar portfolio while maintaining an admirable work-life balance. Her journey into vacation rentals started unexpectedly when her husband purchased their first property just a day before she gave birth to their fifth child! Instead of seeing this as a challenge, Rose embraced the opportunity with incredible determination.With 80% of her bookings coming directly through her website and 60% of her guests being repeat customers, Rose's approach to hospitality is clearly working. In this conversation, we’ll explore how she’s built her brand, diversified her booking sources, and balanced entrepreneurship with motherhood. Whether you're a seasoned host or new to the game, Rose’s insights offer a fresh, inspiring perspective on thriving in the vacation rental world. Let’s dive in!Things we discussed in this episode:Rose Tipka's background as a homeschooling mom of six and how that has shaped her entrepreneurial drive.The unexpected start of her vacation rental business when her husband purchased their first property without her initial knowledge.The importance of maintaining a work-life balance and being present for her family while growing a successful business.Rose's strategic decision to focus on high-end vacation rentals with average daily rates between $600-$1000.The power of branding and how Rose has built a cohesive brand experience across her properties, marketing, and customer interactions.Rose's use of "magic phrases" to reinforce her brand values, such as friendliness and hospitality.The personalized customer service tactics Rose employs, including video greetings, handwritten thank-you notes, and branded fridge magnets.The significance of diversifying booking sources beyond third-party platforms like Airbnb and Vrbo to build a sustainable business.The challenges of unpredictability and account suspensions on OTA platforms, and the importance of having a standalone business.The lessons Rose has learned in balancing entrepreneurship and parenthood, and the "ferocity" that comes with being a mom in business.Get in touch with Rose:Website - https://yourfamilysplace.com/Email - [email protected] - https://www.facebook.com/yourfamilysplaceYouTube - https://www.youtube.com/channel/UCP79fgBZ2vzH2dGUuLavY6AInstagram - https://www.instagram.com/yourfamilysplace_/#SmartStayShow #realestate #realestateinvesting #realestateinvestor #realestatelaw #realestateagent #RealEstateNegotiation #ShortTermRentals #VacationRentalMarketing #VacationRentalBranding #VacationRentalHospitality #VacationRentalManagement #VacationRentalSEO #VacationRentalInfluencers #WorkLifeBalanceEntrepreneur #RemotePropertyManagement #VacationRentalCustomerService #WomenInBusiness*****Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for another episode of SmartStay Show!*****SmartStay Show Website and on Instagram and YouTubePrideaway Stays Website and on Facebook and LinkedInSmartStay Coaching Website and on InstagramStraightforward Short-Term Rentals WebsiteAttorney Rory Gill on LinkedInJason Muth on LinkedIn*****This podcast and these show notes are not legal advice, but we hope you find both entertaining and informative.Hospitality.FMSmartStay 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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Welcome to today’s episode, where we’re diving deep into the world of scaling a short-term rental business. I'm really excited to introduce our guest, Eric Lewis, the founder and owner of Nashville Stays. Eric’s story is one that’s sure to inspire anyone in the vacation rental industry. He started with just one property and grew his portfolio by leaps and bounds, eventually making the bold move to acquire an entire rental management company.
In this episode, we’ll explore how Eric built his business in the highly competitive Nashville market, the challenges he faced while scaling, and the strategies he used to maintain a high standard of service for both guests and homeowners. Whether you’re just starting out or looking to grow your own rental business, you won’t want to miss Eric’s insights and practical advice. Let’s jump in!"
Things we discussed in this episode:
Scaling a short-term rental business beyond a single property
Eric Lewis' journey from managing one property to acquiring a multi-property company
The strategic benefits of acquiring another short-term rental management company
The process of networking and identifying potential acquisition targets
Navigating the legal and structural aspects of the acquisition deal
Strategies for retaining and building loyalty with the acquired clients/homeowners
Eric's transition from a side hustle to a full-time short-term rental entrepreneur
The importance of continuous education and peer support in building confidence
Challenges of balancing a full-time job with running a growing short-term rental business
Eric's plans for solidifying processes, building a strong team, and focusing on future acquisitions
Get in touch with Eric:
Website - https://nashvillestays.com/
Email - [email protected]
Instagram - https://www.instagram.com/nashvillestays/
Linkedin - https://www.linkedin.com/in/eric-lewis-cpa-07638749/
#SmartStayShow #realestate #realestateinvesting #realestateinvestor #realestatelaw #realestateagent #RealEstateNegotiation #ShortTermRentals #AirbnbHost #PropertyManagement #Entrepreneurship #BusinessAcquisition #Nashville #RealEstateInvesting #SideHustletoBusiness #BusinessGrowth #ScalingOperations
*****
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! -
In this engaging episode, we are excited to introduce Bailey Kramer, a 23-year-old real estate entrepreneur who has already carved out an impressive space in the world of short-term rentals and co-hosting. Bailey's real estate journey began in college after reading Rich Dad, Poor Dad, a book that ignited his entrepreneurial spirit. From there, he dove headfirst into various forms of real estate investing, including apartment complexes and fix-and-flips, before finding his true passion and niche in short-term rentals. Leveraging platforms like Airbnb, Bailey quickly built a portfolio that generates passive income and expanded into co-hosting, helping other property owners turn their spaces into successful vacation rentals.
Despite his young age, Bailey has navigated the challenges of being an entrepreneur in an industry often dominated by older, more experienced investors. His resilience and sharp focus have helped him overcome hurdles like skepticism and imposter syndrome. In this episode, Bailey shares his invaluable insights, from creative financing strategies to effective co-hosting methods, and the importance of staying focused on your goals. Whether you're an experienced real estate investor or just starting your journey, Bailey’s story will inspire and equip you with practical tips to thrive in the short-term rental market. Join us as we explore the highs and lows of his remarkable success—all achieved before his 24th birthday!
Things we discussed in this episode:
Bailey's journey into real estate, starting with reading "Rich Dad, Poor Dad" in college
His initial focus on apartment complexes and the pivot to single-family properties
The creative financing strategies he used to acquire his first few investment properties
How he got started in the short-term rental business and the transition to co-hosting
The challenges he faced as a young entrepreneur, including "imposter syndrome"
The mixed reactions he received from older, more traditional real estate investors
The importance of finding your niche and super-serving a specific target market
The differences in mindset and approach between younger and older real estate investors
The lessons he learned from partnership mistakes and the importance of client selection
His decision to drop out of college to focus full-time on his co-hosting business
Get in touch with Bailey:
Youtube - https://www.youtube.com/channel/UC743mBwYcmpRdxMi8juvJ4g
Linkedin - https://www.linkedin.com/in/bailey--kramer/
Instagram - https://www.instagram.com/the_bailey_kramer
Facebook - https://www.facebook.com/bailey.kramer.986
#smartstayshow #realestate #realestateinvesting #realestateinvestor #realestatelaw #realestateagent #shorttermrentals #airbnbhosting #cohosting #entrepreneurship #businessgrowth #mediumtermrentals #insurancecontracts #chasingdreams #youngentrepreneurs #biggerpockets
*****
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! -
Today, we're diving into a topic that’s essential for any serious Airbnb host—achieving and maintaining Superhost status. As a 29-time Superhost, I’ve learned firsthand what it takes to reach this level, and I’m here to share the insights and strategies that helped me get there.
In this episode, we’ll explore the Superhost criteria—like star ratings, response rates, and cancellations—and why earning this title is more than just a badge. I’ll also discuss how Superhosts earn an average of 29% more revenue, and offer actionable tips on how to boost your listing's performance, enhance guest experiences, and keep that all-important Superhost status.
Whether you're aiming to become a Superhost or maintain it, this episode will give you the tools you need to succeed. Let's get started!
Things discussed in this episode:
The criteria for becoming an Airbnb Superhost, including star rating, response rate, number of completed stays, and cancellation rate.
Jason's personal experience as a 29-time Superhost, including the one quarter he narrowly missed the qualification.
The financial benefits of Superhost status, with data showing Superhosts earn 29% more revenue annually.
The quarterly evaluation process for Superhost status and the rolling 12-month assessment period.
Tips for optimizing listings to attract more guests, such as completing all details, crafting an engaging description, and adjusting for seasonality.
The importance of providing exceptional guest experiences through communication, cleanliness, and attention to detail.
Strategies for building a strong review profile, including the value of having a high volume of positive reviews.
Viewing short-term rental properties as a true business and demonstrating to guests that their satisfaction is a priority.
Additional Superhost perks, such as the $100 Airbnb coupon and the Superhost badge.
Jason's invitation for listeners to share their own Superhost journeys and to reach out for assistance.
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 #AirbnbSuperhost #ShortTermRentalSuccess #GuestExperience #ReviewManagement #ListingOptimization #HostingTips #PassiveIncome #PropertyManagement #TravelHacks #AirbnbHosting
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! -
Today we're excited to welcome ZEONA MCINTYRE, a real estate expert known for her creative financing strategies and unique approach to building wealth through short-term and medium-term rentals. ZEONA has an infectious energy and a passion for helping others achieve financial freedom, and we're thrilled to have her join us on the podcast today.
"My biggest value is freedom," Zeona shares. "I want to be able to move around the world in an easeful way." And that's exactly what she's done, living a life most can only dream of - traveling the world, staying in luxurious homes, and getting paid to pet sit along the way. But Zeona isn't just living the dream, she's also helping others achieve it. As a real estate agent, she's built a thriving referral business, connecting investors across the country with the right agents and creative financing solutions for their needs.
From subject-to-deals to seller financing, Zeona breaks down the complexities of these strategies in a way that makes them accessible, even for beginner investors. And with the current market conditions, her expertise has never been more valuable.
Join us as we dive into Zeona's unique approach to real estate, the power of networking, and how she's been able to create the life of freedom she always wanted. This is a conversation you won't want to miss.
Things we discussed in this episode:
The importance of creative financing solutions in the current high-interest rate environment
Zeona McIntyre's expertise in creative financing and her unique approach to getting deals done
Zeona's focus on freedom and flexibility, including her use of short-term rentals, medium-term rentals, and pet sitting
Zeona's journey as an author and the impact of her book on medium-term rentals
Zeona's social media and influencer strategy, including her use of reels to engage her audience
Zeona's house hacking and pet sitting strategies that allow her to travel and live for free
Zeona's approach to building a real estate referral business and the benefits of referral networks
The concept of subject-to deals and the potential risks and benefits associated with them
Insurance considerations and strategies when doing subject-to deals
Practical examples and the flexibility of subject-to deals for both sellers and buyers
Get in touch with ZEONA:
Instagram - https://www.instagram.com/zeonamcintyre/
Facebook - https://www.facebook.com/zeona.mcintyre
STR/MTR Mastermind - https://www.zeonamcintyre.com/mastermind1
30 Day Stay - https://www.zeonamcintyre.com/book
#smartstayshow #humansoverhouses #realestate #realestateinvesting #realestateinvestor #realestatelaw #realestateagent #realestateinvesting #authenticity #storytelling #consistency #hardwork #creativefinancing #subjecttodeals #househacking #petstays #travelhacking #realestatedeals #mortgagetransfers #mediumtermrentals #mtrs #biggerpockets
*****
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! - Visa fler
