SmartStay Show - Short Term Rental Counsel | Airbnb Hosting Tips

By Airbnb Superhost Jason Muth + Rory GillBusiness Investing

SmartStay Show - Short Term Rental Counsel | Airbnb Hosting Tips episodes

January 27Behind the Bold Designs That Maximize Short-Term Rental ROI | Bri West + Jordan McDonough
Ever wondered what makes a short-term rental truly unforgettable?
Some hosts swear by bold color schemes, while others lean into quirky themes, but what really drives bookings and keeps guests coming back?
Today, we sit down with renowned designers Bri West and Jordan McDonough here on SmartStay Show to explore the art and strategy of standout short-term rental design. Discover how bold color, imaginative themes, and strategic branding can transform any property into not just a beautiful space, but an unforgettable guest experience, and a profitable investment.
From emerging market trends to must-have amenities, this episode is packed with actionable insights for both new and seasoned hosts. Whether you’re ready to go all-in on a themed rental or simply considering a design refresh, learn how thoughtful choices can elevate your bookings, enhance guest satisfaction, and maximize ROI.
Things we discussed in this episode:

The importance of bold color patterns and themes for short-term rental success.
Defining and researching the target audience before designing.
Branding properties to create memorable, differentiated guest experiences.
Strategic, ROI-driven design based on market research and data.
Using different design strategies for various markets (urban vs. cabin, vibrant vs. cozy).
Incorporating themes—even bold or unique ones—to boost appeal and bookings.
Leveraging branding (signs, doormats, Wi-Fi) for guest recall and repeat business.
Treating design as an investment to drive revenue, not just an expense.
The growing importance of amenities and functional design in guest experience.
Trends in the short-term rental industry and future growth plans for Summer Led Designs.
Get in touch with BRI & JORDAN:

Instagram - https://www.instagram.com/somerled.designs/?hl=en
Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.somerleddesigns.com/
Linkedin Bri- ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/bri-west-2a7a93288/
Linkedin Jordan- ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jordan-patchell-mcdonough-758a9ba4/?trk=people-guest_people_search-card

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #AirbnbDesign #RentalROI #InteriorDesign #PropertyBranding #VacationRental #GuestExperience #HospitalityTrends

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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!

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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
41 min
January 20What the Top 10% of STRs Are Doing Differently (According to Data) | Kenny Bedwell
What actually makes one short-term rental crush it… while another barely books?

Today we sit down with Kenny Bedwell, a former data analyst turned short-term rental expert, to unpack what truly separates top-performing properties from the rest. We talk about why blending in is the fastest way to lose (and why your rental needs its own “Impossible Whopper”-style edge), how Kenny’s investment strategy has evolved over time, and what most hosts still misunderstand about ROI and aligning with real client goals.

Whether you’re buying your very first property or scaling a growing portfolio, this conversation is packed with real-world, data-backed insights to help you stand out, book more, and build smarter in today’s ultra-competitive short-term rental market.

Things we discussed in this episode:

Kenny Bedwell’s “Impossible Whopper” analogy for making short-term rental properties unique.
The importance of being in the top 10% of rental markets to achieve success.
Kenny’s transition from data analyst to real estate investor and consultant.
How Kenny helps clients find, analyze, and acquire short-term rental properties using data.
The need to align investments with clients’ budgets, ROI goals, and personal preferences.
Setting realistic expectations for short-term rental returns and correcting misconceptions.
The significance of data-driven market analysis and adapting to changing market conditions.
Consulting for current property owners, focusing on guest avatar and unique amenities.
Kenny’s personal portfolio management strategies, use of teams, and focus on scaling up.
Advice for new investors, including the importance of starting research early and leveraging expert resources (like STR Insights’ annual report).
Get in touch with Kenny :

Facebook - ⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/ShortTermRentalInsights
Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strinsights.com/
Instagram - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/strinsights/Youtube - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@strinsights7414
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #STRInsights #VacationRentals #DataDriven #ROI
#UniqueStays #PropertyManagement #InvestSmart
#RentalIncome
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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!

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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
45 min
January 13NEVER Let Emotions Dictate Your Pricing Strategy | Dan Rivers
What does it really take to build a short-term rental business that supports the life you want?
Today we sit down with special guest Dan Rivers from Synergy Stays as they unpack the real motivation behind Dan’s journey, from real estate sales to revenue management expert, all driven by the goal of creating a truly mobile lifestyle.
In this episode, Dan shares practical pricing strategies, why listing optimization is a game-changer, and how shifting your mindset from “side project” to real business can unlock long-term success. Whether you’re a new host or an experienced operator ready to sharpen your strategy, this conversation is packed with takeaways you can put to work right away.
Things we discussed in this episode:

Dan Rivers’ background in real estate and short-term rentals.
The importance of identifying and understanding your personal “why.”
Transition from traditional real estate sales to a mobile business model.
The evolution of Synergy Stays into a revenue management-focused company.
The significance of effective revenue management in today’s competitive market.
Practical pricing strategies, including use of discounting and market data.
The impact of guest reviews and ratings on rental success.
The importance of listing optimization—pictures, keywords, amenities, and descriptions.
Treating short-term rentals as a serious business, not just a hobby.
The crucial role of mindset, goal setting, and continuous improvement in long-term business success.

Get in touch with Dan:

Facebook - ⁠⁠⁠⁠⁠⁠https://www.facebook.com/SynergyStays/
Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.synergystayslocal.com

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #RevenueManagement #AirbnbHost #RemoteWork #ListingOptimization #TravelWithKids #EntrepreneurMindset #PropertyManagement #BusinessGrowth

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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
36 min
January 06Run Your STR Like a Pro With This Tech Stack | Hospitable's Pierre-Camille Hamana
What does it really take to stay ahead as short-term rentals and property management continue to evolve?

In this episode, we sit down with Pierre-Camille Hamana, CEO of Hospitable, for a candid conversation about where the hospitality industry is headed and what hosts need to be thinking about right now. We dive into real-world strategies around automating guest communication, using dynamic pricing to maximize revenue, navigating tax remittance across multiple states, and how Hospitable’s unique Host Token program is designed to better align the platform with the hosts who rely on it every day.

Whether you’re brand new to hosting or managing a growing portfolio, this conversation offers practical insights and forward-thinking ideas to help you stand out, scale with confidence, and build a more resilient hospitality business.
Things we discussed in this episode:

The changing rules of hospitality and the evolving role of Airbnb hosts.
How direct bookings provide control and value for short-term rental owners.
Hospitable’s role in automating communications and professionalizing operations.
Dynamic pricing: its adoption, challenges, and the resulting revenue increase for hosts.
Market observations from 2025, especially post-pandemic supply/demand shifts.
Integrations with platforms like Airbnb and booking.com to streamline property management.
The convenience and professionalism of Hospitable’s direct booking platform.
Tax remittance complexities and Hospitable’s efforts to handle them for hosts.
The Host Token program, allowing customers to invest in and have a stake in Hospitable.
Future priorities: expanding integrations, internationalization, and continuing innovation to serve hosts better.

Get in touch with Pierre:

Linkedin - ⁠⁠⁠⁠⁠https://www.linkedin.com/in/pchamana/⁠
Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://hospitable.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #HospitalityTrends #DirectBooking #PropertyManagement #DynamicPricing #HostLife #RentalInnovation #VacationRental #Hospitable #STRsuccess

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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
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54 min
December 30, 2025Designing for Dollars: The Strategy The Airbnb Hosts Overlook | Erica Dike
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:

The importance of strategy and intention in short-term rental design, beyond aesthetics.
Erica DK’s journey from Airbnb host to professional designer and her “Designing for Dollars” formula.
Balancing guest needs with owner preferences to maximize occupancy and profitability.
How to design for your target guest and create a strong, appealing property identity.
Managing design challenges on a tight budget and prioritizing ROI-driven upgrades.
The role of color and local inspiration in making properties stand out.
Systematizing design project implementation from sourcing to setup for smooth execution.
Common design mistakes and pet peeves in short-term rentals, like poor layout or missing essentials.
Client experiences and success stories, including the “tilted oak” lake house project.
Insights into evolving trends and the value of working with a professional designer or “design coach.”

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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45 min
December 23, 2025What It Really Takes to Merge Two STR Companies | Evan Davison + Evan Montgomery
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:

The process and mindset behind merging two short-term rental businesses into one partnership.
Distinct roles of visionary and integrator, inspired by "Rocket Fuel" and "Traction."
Challenges and operational hurdles in integrating company back-ends, systems, and teams.
Strategies for team building—hiring, training, and retaining VAs, cleaners, and contractors.
Communication methods for maintaining alignment and problem resolution in a partnership.
Vetting and educating owner leads, with a focus on budgets and design expectations.
Maintaining boutique-level service and personal touch as the business scales.
Market differences between Columbus, OH, and other markets like Provincetown, MA.
Balancing business demands with family and fatherhood, planning for parental leave.
The importance of specialized service providers—designers, photographers, real estate agents—and their impact on rental success.
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/
https://www.aestheticpg.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!

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52 min
December 16, 2025How We Helped 200+ Investors Use the STR Loophole | Blake Anthony Carter + Jeremy Courtney
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:

Blake and Jeremy’s rapid growth from three Airbnbs to nearly 100, and their decision to scale down for quality.
Transition from managing co-living, by-the-room properties to focusing on short-term rentals in Austin.
The STR (short-term rental) loophole and its tax benefits for high-income earners investing in real estate.
The importance of building systems and processes for successful property management.
Creative financing strategies, including seller financing and low down payment deals.
Differences between Austin’s investment-driven rental market and markets like Provincetown with more second-home owners.
The unique challenges and rewards of running a business as a married couple.
Building a family legacy and integrating children and family life with business goals.
The role of community events and local networking in growing a short-term rental brand.
Ongoing goals to improve team training, operations, and business scalability for the future.
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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SmartStay Show ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
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50 min
December 09, 20255-Star STR Design That Holds Up (Without Looking Cheap) | Allegra Muzzillo
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:

The importance of designing for guest experience and five-star reviews.
Using performance fabrics and durable materials for longevity.
Standardizing inventory (sheets, towels, dishes) across properties.
Factoring in cleaner efficiency and furniture that’s easy to maintain.
Balancing aesthetics with practicality, especially in coastal environments.
The value of quality over quantity for high-touch items (beds, sofas, dining sets).
Sourcing from wholesalers versus retail for unique, durable, cost-effective pieces.
The impact of great photography and unique décor in attracting bookings.
Considering guest feedback and reviews when making design decisions.
Weighing the pros and cons of designing for a specific demographic versus broad appeal.

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

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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!

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SmartStay Show ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
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Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
37 min
December 02, 2025Is Building a 100 Sq Ft Glamping Cabin Actually Worth It? (Hint: YES) | Melissa Hessney Masters
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
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Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
35 min
November 25, 2025I Walked Away From My W-2 at 47 (Here’s What Happened) | Jeremy DeGrasse
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:

Transitioning from W2 jobs to running real estate/short-term rental businesses.
Challenges and strategies of scaling a business in your 40s versus hustle culture in younger environments.
Inspiration and lessons from the Adirondacks and Lake Placid for property ownership and building.
The partnership between Jeremy and his wife Nicole in operating Drifter Stays, dividing outward and operational responsibilities.
Importance of balancing business ambitions with family life and personal legacy.
Letting go of clients and properties that don’t fit the business’s goals to maintain reputation and reduce stress.
The significance of intentionality and system-building as the business grows.
Adoption and testing of AI-driven tools like Host Buddy for automating guest communications.
The journey and challenges involved in hiring virtual assistants to support business operations.
Practical advice for mid-career professionals on making a successful transition to a new venture.

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

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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
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45 min

About SmartStay Show - Short Term Rental Counsel | Airbnb Hosting Tips

From the publisher's feed

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…