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SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips
Airbnb Superhost Jason Muth + Rory Gill
277 episodes
1 week ago

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!

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All content for SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips is the property of Airbnb Superhost Jason Muth + Rory Gill and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

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!

Show more...
Investing
Business
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Stop DIY Bookkeeping for Your Airbnb Business! | Ben Coons
SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips
36 minutes 11 seconds
1 month ago
Stop DIY Bookkeeping for Your Airbnb Business! | Ben Coons

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:


  • The critical role of financial systems in short-term rental businesses.
  • The evolution and specialization of Keystone Bookkeepers in the STR industry.
  • Challenges and solutions for bookkeeping as you grow from a small operator to managing multiple units.
  • The importance of developing organized, repeatable systems and processes for scalability.
  • Practical habits for keeping accurate, timely records and avoiding costly bookkeeping messes.
  • The onboarding process for clients with messy or inconsistent financial records.
  • The impact of Airbnb’s new fee structure and strategies to adjust commission and owner communications.
  • Owner statements, trust accounting, and the nuances of co-hosting versus property management models.
  • The introduction of new services from Keystone Bookkeepers, including vacation and income tax filing.
  • Guidance on updating contracts and maintaining transparent communication with owners regarding industry changes.

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

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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

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

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!