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Ever wondered if one spontaneous decision could completely change your career? That’s exactly what happened to Jayla Siciliano. While on vacation, she crunched the numbers on a short-term rental, saw its potential, and the next day, put in an offer on her first property.
In this episode of SmartStay Show, Jayla takes us through her journey from that impulsive purchase to building a thriving short-term rental business across multiple states. We dive into the challenges of managing properties remotely, the importance of building a strong local team, and how she scaled her co-hosting operation while maintaining high-quality guest experiences.
Jayla also shares how she overcame imposter syndrome, lessons from past entrepreneurial ventures, and why she’s now expanding into real estate development. Whether you’re a new investor or an experienced host, this episode is packed with insights and inspiration you won’t want to miss!
Things we discussed in this episode:
Jayla’s Unexpected Start in STRs – How a vacation rental stay led to her first property purchase.
Scaling a Short-Term Rental Business – Growing from a single property to managing multiple across states.
Challenges of Remote Property Management – How she successfully operates rentals from across the country.
Building a Strong Local Team – The importance of having reliable "boots on the ground."
Overcoming Imposter Syndrome – Transitioning from a different industry and establishing credibility in STRs.
The Role of Systems and Technology – Using tools like Breezeway and OwnerRez to streamline operations.
Expense & Maintenance Management – The hidden complexities of managing costs and upkeep, especially in snowy climates.
Co-Hosting and Owner Relations – How she convinces owners to trust a remote management model.
Real Estate Investment & Market Strategy – Why she chose Vermont and California for her properties.
Future Plans & Expansion – Her podcast Seed Money and plans to develop properties on her Vermont land.
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Get in touch with Jayla:
Facebook - https://www.facebook.com/jayla.siciliano.akers
Instagram - https://www.instagram.com/atlasvacations/
Website - https://www.atlas-vacations.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #VacationRentals #AirbnbHost #Entrepreneurship #PassiveIncome #RemotePropertyManagement #CoHosting #STRBusiness #FinancialFreedom
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 makes a short-term rental truly unforgettable? In this episode of SmartStayShow, we uncover the secrets behind top-performing vacation rentals with Mark Lumpkin, sales director at STRCRIBS. From bachelorette-themed escapes in Nashville to hidden speakeasies and glow-in-the-dark mini-golf, Mark shares expert tips on designing spaces that attract guests—and boost revenue.
We dive into bold colors, eye-catching murals, and Instagrammable moments that make listings pop. Whether you're a new host or a seasoned investor, this episode is packed with game-changing insights to help you stand out.
Things we discussed in this episode:
Evolving Guest Expectations – How short-term rental guests expect more than they did 10 years ago, making amenities and design essential for success.
Defining Your Guest Avatar – Understanding your ideal guest (families, couples, bachelor/bachelorette groups) and tailoring the rental experience accordingly.
Themed Rentals & Market-Specific Design – Examples like bachelorette-themed homes in Nashville, Disney-themed rentals in Orlando, and ski-lodge aesthetics in Colorado.
High-Impact Amenities – Features that increase bookings, such as hot tubs, barrel saunas, coffee bars, and even pickleball courts.
Balancing Niche vs. Broad Appeal – The risk of hyper-themed rentals (like college football houses) and finding the right level of specialization.
Bold Design & Color Psychology – How vibrant colors, murals, and statement pieces help listings stand out in crowded markets.
Photography & Staging Strategies – Using professional photos, lifestyle images, and seasonal shots to capture attention and increase bookings.
Budget-Friendly Upgrades – Small investments like blackout curtains, high-quality bedding, and unique wall art that enhance guest experience.
Financing for Rental Upgrades – STR Cribs' 0% financing option to help hosts afford high-impact improvements without upfront costs.
Innovative & Unique Amenities – Creative installations like speakeasies, indoor mini-golf, and hidden game rooms to create unforgettable stays.
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Get in touch with Mark:
Linkedin - https://www.linkedin.com/in/mark-lumpkin-84b173142
Facebook - https://www.facebook.com/strcribs
Instagram - https://www.instagram.com/strcribs_/
Website - https://strcribs.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbHosting #STRCribs #VacationRentals #RentalProperty #AirbnbDesign #PassiveIncome #PropertyManagement #TravelExperience
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! -
Saknas det avsnitt?
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Ever wondered what it’s like to live as a digital nomad, staying in over 30 short-term rentals around the world?
In this exciting episode of the Smart Stay Show, we sit down with Eric and Marissa Dingler, a family that sold most of their possessions and turned their home into a life of adventure. From Costa Rica to Liverpool, the Dinglers share their incredible journey and insights into the world of short-term rentals.
As experienced guests, they dive into what makes a great host, the importance of functional spaces, and how to create an unforgettable guest experience. They also explore the impact of short-term rentals on local communities and how hosts can attract the growing digital nomad market.
Plus, Eric offers free consultations for property owners looking to improve their listings!
Don’t miss this captivating conversation packed with valuable tips and real-world insights!
Things we discussed in this episode:
Eric and Marissa Dingler's transition to a nomadic lifestyle, selling 95% of their possessions.
The Dinglers' preferences for short-term rentals, including the need for 5 bedrooms, multiple bathrooms, and a washer/dryer.
The importance of functional spaces, especially in the kitchen and bathroom, from the guest perspective.
The significance of clear communication and responsiveness between hosts and long-term guests.
The Dinglers' philosophy on providing honest, fair ratings based on the host-guest relationship.
The impact of providing multiple keys for long-term guests and the host's responsiveness to requests.
The nuanced view on the effect of short-term rentals on local housing markets and communities.
The Dinglers' approach to integrating into local communities and being good neighbors as digital nomads.
Eric's digital marketing agency and the offer of free consultations for property owners.
The Dinglers' future plans to potentially become short-term rental hosts themselves.
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Get in touch with Eric and Marissa:
Linkedin - https://www.linkedin.com/in/ericdingler/
Facebook - https://www.facebook.com/coastalcitycreative
Instagram - https://www.instagram.com/intransitstudios/
Website - https://intransitstudios.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #Airbnb #AirbnbGuests #GuestExperience #HostCommunication #LocalCommunities #HousingImpact #FunctionalSpaces #RatingSystem #EntrepreneurialSpirit #DigitalNomads
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! -
Can You Build a Thriving Short-Term Rental Business While Working Full-Time?
In this episode, we sit down with Jim McGowan, a seasoned sales professional who has successfully built a profitable short-term rental portfolio—all while maintaining his full-time job!
Jim takes us through his journey, from an early misstep in fractional ownership to fully owning and managing two stunning vacation rentals in Bartlett, New Hampshire: Summit Vista, a condo with breathtaking views, and Lift House, a sought-after ski-in/ski-out property.
How did Jim make it happen? He breaks down his financing strategy, including how he leveraged a home equity line of credit (HELOC) to secure a prime property with a quick cash offer. He also shares the advantages and flexibility of this approach for aspiring investors.
Tune in now to learn how you can start or grow your own short-term rental business without quitting your day job!
Things we discussed in this episode:
Jim's experience with fractional ownership and the limitations it presented.
The decision to transition to full property ownership and the benefits it provided.
The purchase of Summit Vista and the importance of the property's unique selling point (best view in New Hampshire).
The acquisition of Lift House, a ski-in/ski-out property, and the use of a HELOC to finance it.
The advantages of a HELOC, including the ability to make cash offers, flexible rates, and the opportunity to pay down the principal.
The importance of providing excellent customer service and being responsive to guests.
The strategy of focusing on what makes a property stand out in a competitive market.
The impact of the COVID-19 pandemic on Jim's primary sales job and the role of the short-term rental income.
The benefits of sharing the properties with friends and family, while still maintaining profitability.
Jim's advice for new and aspiring short-term rental hosts, emphasizing the need to do the right thing and create a memorable experience for guests.
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Get in touch with Jim:
Facebook - https://www.facebook.com/summitvistanh
Instagram - https://www.instagram.com/summitvistanh/
Airbnb - https://www.airbnb.com/rooms/893469325980802315
https://www.airbnb.com/rooms/1039058125690946596
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #Airbnb #Vrbo #HardMoneyLending #BurrMethod #DebtServiceCoverageRatio #AirDNAData #EquityTapping #MarketDifferentiation #GuestExperience #ShortTermRentalManagement #RentalIncomeOptimization
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! -
Can AI Handle Guest Communication Better Than You?
In this episode of The Smart Stay Show, we sit down with Jay Ulrich, CEO and co-founder of HostBuddy.ai, to explore how AI is revolutionizing short-term rental management.
Jay, a former civil engineer turned short-term rental host, shares his journey from scaling Select Stays to 40 units to developing an AI-powered platform that learns your style, responds like you (yes, even with emojis! 😎), and frees up your time.
Hosts with 1-10 listings get affordable, 24/7 automated guest communication, while larger operators save thousands by replacing virtual assistants. But how does Host Buddy handle tricky guest questions? What’s the future of AI in STRs?
Join Me and Rory as we dive into the impact of AI on hosting and the future of guest communication..
Things we discussed in this episode:
Introduction to Host Buddy and its potential to transform host operations
Jay Ulrich's background as a short-term rental host and the development of Host Buddy
The need for automated guest communications that led to the creation of Host Buddy
Host Buddy's evolution from an external chatbot to a full-blown software platform
Benefits of Host Buddy for smaller hosts with 1-10 properties and larger hosts with 50-70 units
How Host Buddy frees up virtual assistants to focus on revenue-generating activities
The importance of AI learning from past conversations to sound like the host
Challenges of handling situational questions and decision-making with AI
Host Buddy's ability to detect guest sentiment and generate action items
The predicted widespread adoption of AI-powered guest communication in the short-term rental industry
Get in touch with Jay:
Instagram - https://www.instagram.com/hostbuddy_ai/#
Website - https://www.hostbuddy.ai/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #ArtificialIntelligence #GuestCommunication #AutomationInSTR #HostBuddy #STROperations #VirtualAssistants #GuestExperience #IndustryTrends #FutureOfSTR
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! -
Can hard money lending and short-term rentals be the ultimate power duo?
In this episode of The Smart Stay Show, We sit down with David Little, co-founder of Crown Capital Resources, to explore how savvy investors are using short-term rentals as a game-changing exit strategy.
We dig into DSCR loans, the Burr method for vacation rentals, and how tools like AirDNA are influencing lending decisions. David shares insider tips on leveraging your property’s equity and why guest experience is more critical than ever in competitive markets like Austin.
Plus, we discuss the opportunities—and challenges—of hard money lending for short-term rental hosts. Whether you're looking to refinance, scale, or simply understand the numbers, this episode is packed with actionable advice.
Things we discussed in this episode:
The intersection of hard money lending and short-term rentals
How clients are using short-term rentals as an exit strategy for flips or refinancing
The emergence of secondary lenders willing to consider AirDNA data for underwriting
The application of the Burr method to vacation properties
Understanding debt service coverage ratio (DSCR) loans and how they differ from traditional financing
The role of AirDNA data in the underwriting process and its limitations
The niche lending product offered by Crown Capital Resources, allowing investors to tap into equity quickly
The importance of differentiation and guest experience in competitive short-term rental markets
David Little's investment in the short-term rental management company Cribs and the insights he's gained
Strategies for optimizing rental income, such as marketing tactics and understanding operating expenses
Get in touch with David:
Email - [email protected]
Website - https://crowncapitalresources.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #HardMoneyLending #BRRRRMethod #DebtServiceCoverageRatio #AirDNAData #EquityTapping #MarketDifferentiation #GuestExperience #ShortTermRentalManagement #RentalIncomeOptimization
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! -
How did one property cover an entire mortgage—and spark a 30-property empire?
In this episode of the Smart Stay Show, We sit down with Islam Elgarhi, a short-term rental investor and entrepreneur, to uncover how he turned a chance discovery into a thriving business.
From scaling his portfolio with smart systems to creating an AI tool that helps hosts tackle unfair reviews, Islam shares his secrets for success. Plus, we explore how his martial arts background has shaped his mindset for resilience and growth in the fast-paced world of Airbnb hosting.
If you’re ready to learn how innovation and discipline can transform your short-term rental game, this episode is packed with inspiration and actionable insights!
Things we discussed in this episode:
Islam Elgarhi's accidental entry into the short-term rental market by renting out his upstairs unit on Airbnb.
The rapid growth of Islam's portfolio from 1 property to over 30 properties, through a partnership with his brother and a friend.
The importance of developing robust systems and processes to efficiently manage a growing short-term rental business.
Islam's use of outsourcing to a team in Pakistan and later virtual assistants in the Philippines to handle guest communication and operational tasks.
The challenges of dealing with negative Airbnb reviews and Islam's development of an AI-powered tool to help analyze reviews and provide guidance on removal.
The strategy of encouraging detailed negative reviews from guests in order to build a stronger case for review removal.
The benefits of promptly handling damage claims to avoid retaliatory reviews from guests.
Islam's background in martial arts, including grappling and MMA, and how it has influenced his entrepreneurial mindset and success.
The correlation between Islam's achievements in martial arts and his entrepreneurial success, and the importance of balancing these two passions.
The potential for AI to streamline the review removal process and reduce the need for human intervention, while also highlighting the importance of human interaction in prompting and refining AI tools.
Get in touch with Islam:
Linkedin - https://www.linkedin.com/in/islam-elgarhi/
Instagram - https://www.instagram.com/islamelgarhi/
Website - https://modernstayconsulting.com/
Website - https://www.reviewlawyer.ai/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #Airbnb #Entrepreneurship #SystemsDevelopment #VirtualAssistants #ArtificialIntelligence #ReviewManagement #MartialArts #FocusAndDiscipline #InnovationInRealEstate
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! -
Ever wonder why some hosts seem to always get glowing reviews while others struggle?
In this episode of the Smart Stay Show, I’m joined by my business partners Alex Steeg and Kory Himmer to dive into the game-changing power of proactive communication in short-term rental hosting.
We break down how setting clear expectations upfront can prevent negative reviews and enhance guest satisfaction. From booking confirmations to review requests, we share a 5-step strategy to keep your guests informed and your business running smoothly. Plus, we discuss the latest tech tools to streamline communication and make your life easier.
If you’re ready to take your hosting to the next level, this episode is a must-listen!
Things we discussed in this episode:
The importance of setting clear guest expectations to avoid conflicts and negative reviews.
Cory's 5-part proactive communication strategy, including booking confirmations, pre-check-in instructions, post-check-in check-ins, pre-checkout instructions, and review requests.
The challenges of guests not reading provided materials and the need for patience and understanding.
The value of having physical copies of property instructions in addition to digital guides.
The use of automated messaging systems and AI-powered responses to streamline communication.
The significance of a host's response rate in indicating their overall communication abilities.
The benefits of having friends or family test the property to identify potential quirks and questions.
The importance of being proactive in setting expectations and having detailed instructions.
The need for hosts to stay updated on new technologies and trends in guest communication.
The overall emphasis on providing an exceptional guest experience through effective communication.
Get in touch with Kory:
Facebook - https://www.facebook.com/kory.himmer
Instagram - https://www.instagram.com/603bnb/
Website - https://603bnb.com/ / https://www.smartstaycoaching.com/
Get in touch with Alex:
Facebook - https://www.facebook.com/alex.steeg86
Instagram - https://www.instagram.com/alexsteeg/
Website - https://www.shorewaymgmt.com/ / https://www.smartstaycoaching.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #GuestCommunication #ProactiveHosting #AirbnbHosting #VRBOHosting #GuestExperience #AutomatedMessages #AIResponses #HostingTips #STRSuccess
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! -
Ever Dealt With a Water Damaged 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 water damaged 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:
Water Damaged Nightmare and Insurance Savior - Jason and Rory's experience with a water damaged 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!
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! -
Ever wondered how hostels are redefining the travel experience?
In this episode, I sit down with Nate St Cyr, the visionary co-founder of Malama Capital and Howzit Hostels, to uncover how he’s revolutionizing the traditional hostel concept. From daily pancake breakfasts and Margarita nights to crafting a vibrant, community-driven atmosphere, Nate shares his journey of turning a simple idea into a thriving hospitality brand.
We dive into how Generation Z’s desire for connection inspired his approach, the power of social media and influencer partnerships, and his innovative strategies for building an empowered team. If you’re curious about the future of travel, hospitality, or entrepreneurship, this is an episode you won’t want to miss!
Tune in now to hear Nate’s incredible story and get inspired to think differently about what it means to create unforgettable travel experiences. Let’s go!
Things we discussed in this episode:
The evolution of the global hostel industry and the recognition of it as a significant investment opportunity.
Nate St Cyr's background and his partnership with a business partner experienced in short-term rentals.
The misconceptions about hostels and how How's It Hostels offers a unique, community-driven experience.
The amenities and programming at How's It Hostels, including daily activities, shared spaces, and community-building events.
The importance of understanding the target audience, particularly Generation Z, and their preferences for shared experiences and human connection.
The strategic use of social media and influencer collaborations to market the hostels and reach their ideal guests.
The high-touch approach to guest experience, including pre-arrival welcome calls and 24/7 reception.
The company's focus on creating a positive work culture and retaining employees through generous vacation policies and empowerment.
The plans for expansion and the need to understand the local market and hospitality needs when scaling the business.
The importance of aligning the business model and hospitality offerings with the target audience's needs and preferences.
Get in touch with Nate:
Facebook - https://www.facebook.com/howzithostels
Instagram - https://www.instagram.com/howzithostels/
Website - https://www.howzithostels.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #Hostels #HospitalityIndustry #CommunityExperience #GenerationZ #SocialMediaMarketing #GuestExperience #EmployeeRetention #HospitalityEntrepreneurship #TravelTrends #HowsItHostels
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 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! -
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
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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! -
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
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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! -
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
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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
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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! - Visa fler
