Welcome to the SmartStay Show, your go-to podcast for mastering Short-Term Rentals on Airbnb, Vrbo, and beyond. For more Airbnb tips, visit smartstayshow.com and smartstaycoaching.com.
Hosted by 30-time Airbnb Superhost Jason Muth and Real Estate Attorney Rory Gill, we equip you with the tools to launch, manage, and optimize your vacation rental like a pro.
Unlike other shows, we specifically cater to owners of small-but-mighty portfolios who self-manage their properties. Each episode delivers expert insights, legal tips, and proven strategies from successful hosts across the U.S. Whether you’re buying your first property, improving your listing, or looking to stay ahead of the competition, we offer actionable advice and real-life stories to help you thrive.
From pricing strategies to guest communication, we provide the playbook to turn your property into a top-performing rental. Subscribe now and unlock your rental’s full potential with the SmartStay Show!
Welcome to the SmartStay Show, your go-to podcast for mastering Short-Term Rentals on Airbnb, Vrbo, and beyond. For more Airbnb tips, visit smartstayshow.com and smartstaycoaching.com.
Hosted by 30-time Airbnb Superhost Jason Muth and Real Estate Attorney Rory Gill, we equip you with the tools to launch, manage, and optimize your vacation rental like a pro.
Unlike other shows, we specifically cater to owners of small-but-mighty portfolios who self-manage their properties. Each episode delivers expert insights, legal tips, and proven strategies from successful hosts across the U.S. Whether you’re buying your first property, improving your listing, or looking to stay ahead of the competition, we offer actionable advice and real-life stories to help you thrive.
From pricing strategies to guest communication, we provide the playbook to turn your property into a top-performing rental. Subscribe now and unlock your rental’s full potential with the SmartStay Show!
Can intentional design actually boost your short-term rental profits?
Find out in this week’s episode featuring Vacation Rental Design Strategist Erica Dike. We dive into why the most successful rentals combine eye-catching style with smart strategies for ROI.
Erica shares her journey from student Airbnb host to expert designer, offering actionable tips for balancing personal taste with guest appeal, all while maximizing profitability.
Whether you’re an investor, homeowner, or design enthusiast, this episode is packed with stories, expert advice, and practical insights you can use for your next project.
Subscribe and hit the notification bell so you never miss an episode!
Things we discussed in this episode:
Get in touch with Erica:
Linkedin - https://www.linkedin.com/in/erica-dike/
Website - https://www.ericaooh.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #BusinessPartnership #VacationRental #Entrepreneurship#PropertyManagement #TeamBuilding #STRBusiness#RealEstateInvesting #WorkLifeBalance #RentalSuccess
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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
Is going solo really the best way to scale a short-term rental business—or can the right partnership take you further, faster?
In this episode, we sit down with Evan Davison and Evan Montgomery to unpack what actually happens when two ambitious operators decide to merge their short-term rental businesses. We talk openly about dividing roles using the visionary and integrator model, building trust, and navigating the real challenges of scaling while maintaining a boutique guest experience.
The conversation also explores team leadership, growing pains, and how personal life and fatherhood intersect with running a fast-growing STR operation. This episode offers honest insights, real lessons, and practical perspective for anyone considering partnership or scaling in the short-term rental space.
Things we discussed in this episode:
Get in touch with Evan Davison and Evan Montgomery:
Instagram - https://www.instagram.com/aesthetic_p.g/
Facebook - https://www.facebook.com/AestheticPropertyGroup
Website - https://www.stupendousstays.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #BusinessPartnership #VacationRental #Entrepreneurship
#PropertyManagement #TeamBuilding #STRBusiness
#RealEstateInvesting #WorkLifeBalance #RentalSuccess
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
What does it really take to scale a short-term rental business, and when does “more” stop meaning “better”?
In this episode, we sit down with Blake and Jeremy from Cribs Consulting, the powerhouse duo behind one of Austin’s most respected short-term rental operations. We dig into their journey from managing just three Airbnbs to nearly a hundred properties, and the surprising decision to intentionally scale back in order to gain clarity, profitability, and balance.
We talk candidly about creative financing strategies, tax-smart moves like the STR loophole, and what it truly means to build a long-term, legacy business alongside your spouse. Blake and Jeremy also share how community events, genuine relationships, and showing up authentically for clients have been key drivers of their success.
If you’re a host, investor, or entrepreneur questioning how to grow smarter, not just bigger, this conversation is packed with real-world insight, hard-earned lessons, and plenty of inspiration.
Things we discussed in this episode:
Get in touch with Blake and Jeremy:
Instagram - https://www.instagram.com/cribsconsulting/
Linkedin - https://www.linkedin.com/in/jeremy-courtney/
Website - https://www.cribsconsulting.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #AirbnbHost #STRloophole #CreativeFinancing #FamilyBusiness #PropertyManagement #CommunityBuilding #VacationRental #Entrepreneurship
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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
What really makes a short-term rental unforgettable—and consistently five-star worthy?
In this episode, we sit down with Allegra Muzzillo—editor-turned-designer, superhost, and one of the sharpest minds in STR design—to uncover the secrets behind creating guest-ready spaces that truly stand out.
Allegra shares her fascinating journey from the fast-paced world of NYC publishing to crafting beautifully designed, highly functional rentals. We dive into the exact design decisions that matter most: choosing durable, cleaner-friendly materials, standardizing essentials to streamline turnovers, and integrating thoughtful local touches without falling into overdone clichés.
Whether you’re a seasoned host looking to elevate your listings or setting up your very first property, this episode is packed with real-world, actionable strategies to help you boost guest satisfaction, simplify operations, and increase profitability.
🎧 Tune in and learn how to design spaces guests can’t wait to book.
Things we discussed in this episode:
Get in touch with Allegra:
Instagram - https://www.instagram.com/acminteriors/
Facebook - https://www.facebook.com/ACMinteriorsFLA
Website - https://www.acminteriors.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #AirbnbHost #InteriorDesign #VacationRental #Superhost #RentalSuccess #HomeDecor #DesignTips #RentalProperty #GuestExperience
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
How do you turn a rustic flower farm into the Northeast's most enchanting glamping experience?
On this episode, I step into the heart of the Vermont woods to chat with the incredible Melissa Hessney Masters, the creative force behind Tangle Bloom. This conversation is all about transformation: how Melissa took a rustic flower farm and her deeply imaginative spirit and turned it into one of the most sought-after glamping retreats in the entire Northeast.
Melissa walks us through her journey, sharing how a tiny, 100-square-foot cabin became a genuine sanctuary for city dwellers craving nature and slow living. We dig into the details of her success, from the thoughtful touches—think fresh-cut wildflower bouquets and the magic of a wood-fired hot tub—that set her experience apart, to the practical realities of managing guest expectations in an off-grid environment.
If you’ve ever wondered what it takes to cultivate an authentic, successful hospitality business, Melissa's story of building Tangle Bloom is a must-listen. You're going to leave this episode inspired to completely reimagine what true hospitality looks like.
Things we discussed in this episode:
How Melissa turned a 100 sq. ft. cabin on her Vermont flower farm into a popular glamping stay.
The shift from personal use to rental after friends encouraged her.
Off-grid guest perks like wildflower bouquets, a wood-fired hot tub, and thoughtful hospitality.
Using Airbnb and Hipcamp to manage bookings and diversify income.
Adding outdoor showers, kitchens, and composting toilets for guest comfort.
Attracting mostly urban, younger couples who book two-night stays.
Adjusting pricing for weekends vs. weekdays and navigating seasonal demand.
Balancing guest expectations while keeping listings accurate.
Growing community through social media, creators, and local outreach.
Future plans for new projects and gathering ongoing guest feedback.
Get in touch with Melissa:
Instagram - https://www.instagram.com/tanglebloom/
Facebook - https://www.facebook.com/tanglebloomflowers/
Website - https://tanglebloom.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Glamping #TinyCabin #Vermont #FlowerFarm #AirbnbHost #OffGridLiving #SustainableTourism #SlowLiving #SmartStay #NatureRetreat
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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
Ever wonder what it really takes to walk away from a steady W2 and reinvent your life in real estate and short-term rentals?
In this episode, host Jason Muth sits down with Jeremy De Grasse for an honest, inside look at how they each stepped out of corporate careers and built thriving businesses in the stunning Adirondacks. Together, they dive into the lessons learned the hard way, the juggling act of family and entrepreneurship, the importance of scaling with intention, and how tools like Host Buddy can transform your operations.
If you’re dreaming about your own career shift or looking to grow your rental portfolio, their candid conversation is packed with inspiration, insights, and real-world advice to help you shape your next chapter.
Things we discussed in this episode:
Get in touch with Spencer:
Instagram - https://www.instagram.com/drifterstays/
Facebook - https://www.facebook.com/drifterstays
Website - https://www.drifterstays.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #CareerChange #EntrepreneurLife #MidlifeReinvention
#BusinessGrowth #PropertyManagement #FamilyBusiness #AIAutomation #WorkLifeBalance
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
What happens when a pro athlete walks away from the game and builds an entirely new kind of success?
In this episode, I had an in-depth conversation with former MLS goalkeeper Spencer Richey to explore his remarkable transition from the world of professional soccer to thriving real estate entrepreneur. Spencer shares the pivotal mindset shift that allowed him to step away from sports, the courage it took to reinvent himself, and the excitement he found in helping others grow their wealth through innovative real estate opportunities.
You’ll hear Spencer break down the vision behind launching Sound Stays and The Missing Hotel, the real challenges of starting from scratch, and how he uses lessons from the field—discipline, resilience, and teamwork—to earn trust from investors and partners. He also opens up about balancing ambitious hospitality projects with the realities of family life, all while continuing to scale his growing portfolio.
If you’re curious about career pivots, real estate investing, or the personal growth that comes with betting on yourself, this conversation offers real, honest insights you won’t want to miss.
Things we discussed in this episode:
Spencer’s MLS-to-Real-Estate Career Pivot
The Rise of Sound Stays in Seattle
Leaving Pro Sports & Redefining Identity
Building The Missing Hotel in Texas
Launching Clear Line Capital
Raising Private Capital & Investor Trust
Scaling Operations & Building a Team
Balancing Family Life with Entrepreneurship
Guiding Pro Athletes in Wealth Building
Future Expansion Plans & Missing Island Project
Get in touch with Spencer:
Instagram - https://www.instagram.com/missinghoteltx/
Facebook - https://www.facebook.com/missinghoteltx/
Website - https://www.missinghotel.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #CareerTransition #Entrepreneurship #HospitalityIndustry #AthleteToEntrepreneur #WealthBuilding #PersonalGrowth #LeadershipJourney #PodcastEpisode
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
Ever wondered what it really takes to make a vacation rental truly pet-friendly—and profitable? 🐾
In this episode, we sit down with John Bradford and Mike Shytle from Petscreening to unpack the world of pet screening and what it means for both hosts and guests. We dive into how hosts can build trust with pet-loving travelers while navigating the practical and legal challenges that come with allowing pets.
Rory shares his firsthand experience managing pet-friendly properties, and together we explore how clear policies, fraud prevention, and smart tech integrations are shaping the future of the vacation rental industry. Join us for a candid, insightful conversation about how technology, transparency, and good communication can make every stay smoother—for guests, hosts, and our furry friends alike.
Things we discussed in this episode:
The value and functionality of pet screening for vacation rentals
Financial and booking advantages of pet-friendly properties
Clear pet policies that protect owners and enhance guest trust
How Pet Screening supports compliance and policy management
Addressing service animal fraud and ensuring legitimate accommodations
Building digital pet profiles and tracking incident data
Managing pets in condos and HOA-regulated properties
Best practices and amenities for welcoming pets
Integrations with major property management and booking platforms
Pet Screening’s social mission: Fido Alert and Tabby Alert lost pet recovery
Get in touch with John or Mike:
Instagram - https://www.instagram.com/petscreening/
Facebook - https://www.facebook.com/PetScreening/
Website - https://www.petscreening.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #PetScreening #VacationRentals #PetFriendly
#PropertyManagement #ServiceAnimals #RentalTrends
#AirbnbHosts #PetPolicies #LostPets
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
What happens when an ice cream shop owner decides to reinvent hospitality in the heart of bourbon country? 🍨🥃
In this episode, we sit down with Andrew Llewellyn, the creative force behind some of Louisville’s most exciting group-focused short-term rentals. From transforming forgotten commercial buildings into stylish hangout destinations to curating unforgettable experiences for bachelor parties, corporate retreats, and bourbon-loving travelers, Andrew has mastered the art of blending comfort, design, and storytelling.
Tune in as Jason and Andrew dive into how a bold vision — and a little Kentucky grit — can turn overlooked spaces into thriving hospitality hubs. You’ll hear about the power of niche marketing, the importance of creating experiences (not just accommodations), and what it really takes to stand out in today’s competitive short-term rental world.
Whether you’re an aspiring host, an entrepreneur, or just love a great reinvention story, this conversation will leave you inspired to think bigger about what’s possible in hospitality.
Things we discussed in this episode:
Get in touch with Andrew:
Instagram - https://www.instagram.com/iamandrewllewellyn/
Facebook - https://www.facebook.com/Superstayslouisville/
Website - https://andrewllewellyn.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #GroupTravel #Hospitality #LouisvilleKY #BourbonTrail #VacationRental #TravelPodcast #Entrepreneurship #SmartStays
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
Ever wondered what it takes to leave a tech career and build a thriving short-term rental business?
In this episode, Morgan Steir joins me to share his journey from tech sales to managing a successful lakeside cabin in New Hampshire.
Hear his honest insights on self-managing rentals, launching a home services franchise, and mastering everything from guest experience to vendor challenges.
A must-listen for anyone looking to grow as a host and entrepreneur.
Things we discussed in this episode:
Get in touch with Morgan:
Instagram - https://www.instagram.com/undercoverundercoaters/
Facebook - https://www.facebook.com/profile.php?id=61582390307696
Website - https://www.undercoverundercoaters.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #PropertyManagement #Entrepreneurship #SelfManagement #HomeServices #RentalSuccess #HostTips #GuestExperience
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
What makes some short-term rental listings instantly irresistible while others get scrolled past? 🎥
Join us and real estate photographer Kaylee DeCollibus as we dive into the secret sauce of standout listings — professional photos! Discover how eye-catching imagery goes beyond first impressions to shape guest experience, drive bookings, and capture a property’s true vibe.
From creative staging to lighting techniques and must-know do’s and don’ts, this episode shows why smart photography leads to smart stays — and lasting success.
Things we discussed in this episode:
Get in touch with Kaylee:
Instagram - https://www.instagram.com/kaydphoto_/
Facebook - https://www.facebook.com/Kaydphoto/
Website - https://www.kaydphoto.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #VacationRental #AirbnbHost #RealEstatePhotography #PropertyPhotos #RentalSuccess #HostTips #ProfessionalPhotography #GuestExperience #SmartStay
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
In this episode, we sit down with Ben Koons from Keystone Bookkeepers to unpack the unique challenges of managing finances in the short-term rental world. From early days of DIY spreadsheets to implementing professional systems, they explore what it takes to build scalable, stress-free bookkeeping practices for growing portfolios.
Jason and Ben also break down Airbnb’s new fee structure, share practical tips for owner reporting, and highlight fresh service offerings designed to support property managers. Whether you’re just starting out or overseeing dozens of listings, you’ll come away with actionable insights to streamline your financial processes, boost profitability, and protect your business as you grow.
Things we discussed in this episode:
Get in touch with Ben:
Youtube - https://www.youtube.com/@KeystoneBookkeepers
Facebook - https://www.facebook.com/KeystoneBookkeepers
Website - https://keystonebookkeepers.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Bookkeeping #PropertyManagement #AirbnbHosts #RentalBusiness #STRIndustry #OwnerReports #TaxStrategy #BusinessGrowth
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
What if the key to short-term rental success isn’t just location, but insight?
In this episode, we sit down with Jamie Lane, Chief Economist at AirDNA, for a masterclass on data-driven investing in the STR space. From his roots as a self-proclaimed “data nerd” to becoming a hands-on host himself, Jamie shares how powerful analytics and real-world experience intersect to shape smarter investment strategies.
Whether you're scouting your first property or scaling a multi-unit portfolio, you'll learn how to identify the right markets, unlock your property's potential, and leverage AirDNA’s industry-leading tools to stay competitive. Plus, Jamie weighs in on emerging market trends and offers a candid forecast on where the industry is headed. Packed with practical insights and real-world advice, this is essential listening for anyone serious about succeeding in the short-term rental game.
Things we discussed in this episode:
Get in touch with Jeremy:
Instagram - https://www.instagram.com/jamie_lane/
Website - https://www.airdna.co/
Linkedin - https://www.linkedin.com/in/jamiehlane/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #STRInvesting #AirDNA #VacationRental #PropertyManagement #RentalData #HostingTips #MarketTrends #SmartInvesting
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
What happens when an ICU nurse brings his heart for care into the world of short-term rentals?
In this episode, we sit down with Jeremy Rosen, who’s turned his passion for helping people into a thriving business managing over 20 properties—all while still working hospital shifts. He shares how compassion, clear systems, and smart tech have helped him scale without losing the personal touch.
From building trust with guests and owners to using tools like Host Buddy and Happy Guest, Jeremy walks us through the strategies that keep his operation running smoothly. Hosts Jason and Rory also dive into the power of reviews, building a reliable team, and the behind-the-scenes systems every successful host needs.
Whether you're just starting out or managing multiple units, this episode is packed with real-life insights and practical tips to help you grow your short-term rental business—and create five-star guest experiences every time.
Things we discussed in this episode:
Get in touch with Jeremy:
Instagram - https://www.instagram.com/@yourhomeawaymgmt/
Facebook - https://www.facebook.com/YHAMLLC
Website - https://yham.host/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Hospitality #AirbnbHost #GuestExperience #RentalBusiness #STRSuccess #HostTips #VacationRental #HospitalityTech
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
Is the future of hosting all about midterm rentals?
In this episode, we chat with Katie Lyon from Furnished Finder to uncover why midterm stays are gaining major traction—and why they’re no longer just for travel nurses. From contractors and relocating families to corporate nomads, a whole new wave of guests is looking for furnished, flexible housing options.
Katie shares real-world strategies to help hosts stand out in this growing space. She breaks down how to optimize your calendar, set clear expectations with guests, and make sure your property is properly protected. Whether you’re already hosting short-term rentals or just curious about new income opportunities, this episode is packed with smart, practical advice to help you boost occupancy, increase revenue, and stay ahead of the curve.
Tune in and discover how midterm rentals might be your next big move.
Things we discussed in this episode:
Get in touch with Katie:
Instagram - https://www.instagram.com/furnishedfinder/
Facebook - https://www.facebook.com/FURNISHEDFINDER
Website - https://www.furnishedfinder.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #MidtermRentals #FurnishedFinder #RentalProperty #PropertyManagement #TravelNurseHousing #CorporateHousing #HostTips #SmartStay
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
Ever wonder how a beachfront condo in Provincetown could become a gold mine?
In this episode, we sit down with Kareem Sanjaghi—Prideaway Stays’ very first client—to hear how he went from mortgage officer to full-time musician and savvy real estate investor. Kareem shares the story behind his short-term rental success, the importance of location in the Cape Cod market, and the ups and downs of managing property in a seasonal town. We dive into building strong partnerships, navigating challenges, and blending personal passion with smart investing. If you're curious about turning property into profit, this conversation is a must-watch.
Things we discussed in this episode:
Get in touch with Kareem:
Instagram - https://www.instagram.com/thekareemofthecrop/
Facebook - https://www.facebook.com/thekareemofthecrop
Website - https://www.kareemdrums.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Provincetown #CapeCod #PropertyManagement #Entrepreneurship #VacationRental #MusicianLife #SmartInvesting #PersonalGrowth
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
What if one tool could organize your entire short-term rental business—and actually give you your time back?
In this episode, we sit down with hospitality veteran turned systems expert Michael Dinwiddie to talk about the real-world challenges of managing short-term rentals and how the right systems can transform your operation from chaos to calm. Michael shares how he uses Notion as a “second brain” to streamline everything from SOPs to onboarding, and why even single-property hosts can benefit from getting organized early.
The conversation dives into practical strategies for empowering virtual assistants, leveraging AI, and building a business that runs smoothly—even when you’re not around. Whether you’re just starting out or scaling up, this episode is packed with insights and inspiration to help you get out of the weeds and take control of your business.
Things we discussed in this episode:
Get in touch with Michael:
Instagram - https://www.instagram.com/cometogethere/
Facebook - https://www.facebook.com/togetherevacationrentals
Website - https://togetherevacationrentals.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals AirbnbHost #PropertyManagement #Notion #BusinessSystems #VacationRental #Automation #TeamBuilding #HospitalityIndustry #ProductivityHacks
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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
Can Last-Minute Bookings Actually Boost Your STR Revenue?
Last-minute bookings aren’t just a backup plan anymore—they’re becoming a key revenue strategy for short-term rental hosts. In this episode, we sit down with Alex Alioto, co-founder of Whimstay, about how shifting traveler behavior—especially among Gen Z and millennials—is reshaping the way hosts think about occupancy, pricing, and calendar gaps.
Alex shares how Whimstay helps property owners capture value from expiring inventory, extend the shoulder season, and stay ahead of modern travel trends. The conversation dives into how hosts can adapt their strategies to meet rising demand for flexibility, while still delivering standout guest experiences.
Whether you’re a seasoned host or just exploring the STR space, this episode offers fresh insight into the future of vacation rental booking behavior—and how to make it work in your favor.
Things we discussed in this episode:
Get in touch with Alex:
Instagram - https://www.instagram.com/whimstay/
LinkedIn - https://www.linkedin.com/company/18786646/admin/dashboard/
Website - https://www.whimstay.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #VacationRentals #LastMinuteBookings #TravelTrends #Whimstay #GenZTravel #MillennialTravel #PropertyManagement #DynamicPricing #GuestExperience
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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
What does it really take to break free from the 9-to-5 and build a thriving short-term rental business?
In this episode, We sit down with Jake Martin, a former corporate professional who left the security of his W2 job to chase a different kind of success—one built on freedom, flexibility, and financial independence.
Jake opens up about the real story behind his transition: the fears, the failures, and the big wins. From learning the ropes of vacation rental investing in San Diego to managing multiple properties and navigating tough decisions, Jake shares hard-earned lessons and no-fluff advice for anyone dreaming of a similar leap.
Whether you're exploring co-hosting, thinking about your first property, or simply craving a raw and honest take on entrepreneurship, this episode delivers both inspiration and actionable insights.
🎧 Tune in and get ready to rethink what’s possible.
Things we discussed in this episode:
Get in touch with Jake:
Email - info@lodgeandleisure.com
LinkedIn - https://www.linkedin.com/in/jacob-r-martin
Website - https://www.lodgeandleisure.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Entrepreneurship #VacationRentals #PropertyManagement #CoHosting #FinancialFreedom #BusinessGrowth #AirbnbHost #InvestSmart
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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
What if you could run a thriving real estate business from anywhere in the world—without ever setting foot in most of your properties?
In this episode, we sit down with Adrienne Green, a savvy real estate investor who turned house hacking into a passport for full-time travel with her family. She shares how she built rock-solid systems, empowered virtual assistants, and mastered the art of delegation—managing properties she hasn’t visited in years.
You’ll hear how Adrienne creates SOPs that keep her business running smoothly, leverages AI tools for smarter decisions, scales without burning out, and stays true to her values while building wealth. Whether you’re a seasoned investor or just starting out, her story will inspire you to design a business that works for you, not the other way around.
Press play and get ready to rethink what’s possible for your real estate journey.
Things we discussed in this episode:
Get in touch with Adrienne:
Facebook - https://www.facebook.com/ARealGreen123
Instagram - https://www.instagram.com/arealgreen/
Website - https://adriennegreen.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #VirtualAssistants #PropertyManagement #BusinessSystems #Automation #TimeFreedom #Entrepreneurship #AIinBusiness #SOPs
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