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:

1. Andrew Llewellyn’s journey from ice cream shops to short-term rentals.
2. Repurposing commercial buildings for large-group lodging.
3. Hosting bachelor parties and corporate retreats under one roof.
4. Integrating unique local experiences, especially bourbon-centric activities.
5. Overcoming challenges with permits, city officials, and securing bank financing.
6. Booking trends, windows, and group sales strategies.
7. Handling guest communications for large groups and ensuring personalized hospitality.
8. Innovative cleaning processes, staff management, and keeping costs down.
9. Marketing approaches using SEO, OTAs, and targeting conventions.
10. Advice for aspiring hosts: mentorship, vision, and niching for business success.

Get in touch with Andrew:

Instagram - https://www.instagram.com/iamandrewllewellyn/

Facebook - ⁠⁠https://www.facebook.com/Superstayslouisville/

Website - ⁠⁠https://andrewllewellyn.com/

https://superstaysstr.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:

1. Morgan Steir’s transition from tech sales to launching a short-term rental business.
2. The importance and challenges of self-managing a rental property.
3. Guest experience, feedback, and adapting operations to improve reviews.
4. The financial benefits and realities of owning a vacation rental.
5. Launching “Undercover Undercoatings,” a vehicle services franchise.
6. Dealing with platform policy changes and power dynamics (e.g., Airbnb).
7. Managing and maintaining amenities like hot tubs and handling related guest claims.
8. Handling property damage, insurance policies, and navigating claims.
9. Building strong vendor relationships and paying for quality service.
10. The value of coaching from Smart Stay to fast-track rental success and avoid common pitfalls.

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:

• The vital role of professional photos in short-term rental bookings and first impressions.
• Kaylee Decollibus’s background and self-taught journey into real estate and rental photography.
• The difference between photographing real estate listings versus short-term rentals.
• How creative, detailed photography enhances a rental’s online personality and guest appeal.
• The importance of wide versus close-up/detail shots for marketing and social media.
• Optimal conditions and lighting for property photography, including weather and natural versus artificial light.
• Use of virtual staging and editing, with a focus on truthful property representation.
• Practical tips and checklists for property owners before a professional shoot.
• The impact of property preparation, like decluttering and proper lighting, on the final photos.
• How smart, intentional photography ties into the broader success and guest experiences for vacation rental businesses.

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:

• 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

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:

• • 
    
  • Jeremy Rosen’s transition from ICU nurse to short-term rental operator.
  • 
    
  • Balancing a full-time nursing career with managing 20+ rental properties.
  • 
    
  • Building trust with guests through personalized communication and profile strategies.
  • 
    
  • Managing guest reviews and encouraging five-star feedback.
  • 
    
  • Handling negative or unusual guest reviews and learning from criticism.
  • 
    
  • The importance of systems and automation for scaling property management.
  • 
    
  • Building and managing a team, including local staff and virtual assistants.
  • 
    
  • Leveraging tech tools like Host Buddy and Happy Guest for messaging and upsells.
  • 
    
  • Owner relations and setting expectations for property management.
  • 
    
  • Strategies for business growth, including marketing, lead generation, and targeting ideal properties.

  
  

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:

• • The importance of systematizing short-term rental operations to reduce chaos and anxiety.
• • Using Notion as a “second brain” to organize property information, SOPs, and tasks.
• • The benefits of documenting processes for scalability and team empowerment.
• • Leveraging Notion’s AI features to summarize SOPs and answer operational questions.
• • Onboarding and training new team members, including local operations managers and virtual assistants.
• • The transition from handling everything personally to delegating guest communications and tasks.
• • Building recurring task systems for proactive property maintenance.
• • The value of empowering and trusting your team to deliver excellent service.
• • Personal stories about business growth, work-life balance, and learning from experience.
• • Michael Dinwiddie’s journey in hospitality, business expansion, and creating training resources for others.

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

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

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:

• The strategy and benefits of filling last-minute gaps in vacation rental calendars.

• How Gen Z and millennial travelers are driving the trend toward shorter booking windows.

• The founding story and unique value proposition of Whimstay as a last-minute rental marketplace.

• The importance of a diverse distribution strategy for property owners.

• Differences in traveler behavior and expectations across generations.

• The impact of remote work on travel patterns and booking flexibility.

• Operational challenges, such as integration with property management systems and avoiding double bookings.

• Pricing strategies, including last-minute discounts and dynamic pricing tools.

• The potential to extend the shoulder season and increase off-season bookings.

• The role of guest experience and local touches in attracting modern travelers.

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

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 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:

• Jake Martin’s decision to leave his corporate job and pursue real estate investing.
• The impact of corporate layoffs and lack of loyalty on career choices.
• Early investments in syndication deals and short-term rentals.
• The process and challenges of renovating and managing properties during COVID.
• Transitioning personal residences into income-generating short-term rentals.
• The financial strategy of covering mortgages through rental income.
• Building and growing a co-hosting business (Lodge and Leisure) in San Diego.
• Methods for finding and acquiring new property management clients.
• Common issues faced by property owners, such as maintenance, design, and guest experience.
• Advice for aspiring entrepreneurs and real estate investors, emphasizing adaptability and problem-solving.

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

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 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:

• 
  
• How real estate investing can provide freedom to travel and grow a business.
• 
  
• The importance of building systems and processes for property management.
• 
  
• Transitioning from hands-on management to leveraging virtual assistants.
• 
  
• Treating all properties, even local ones, as long-distance investments to enforce systems.
• 
  
• Using technology tools like OpenPhone, Hospitable, and Host Buddy for communication and automation.
• 
  
• The challenges and benefits of hiring and training virtual assistants.
• 
  
• Creating and optimizing standard operating procedures (SOPs) using screen recordings and AI.
• 
  
• Integrating SOPs and training materials into platforms like Notion for team onboarding.
• 
  
• Adrienne’s upcoming book and VA LaunchPad course for real estate investors.
• 
  
• The importance of aligning business decisions with personal values.

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

What does it take to turn a remote West Texas ghost town into an Instagram-worthy short-term rental experience?

In this episode, discover how a former NYC creative director brought his branding expertise to the desert to create the cinematic Ghost Town Casitas. Learn how storytelling, design, and photography come together to craft rentals that offer more than just a stay—they deliver an unforgettable experience.

Join us as we explore the challenges of building in remote areas, the power of great photos, influencer stays, and balancing family life with entrepreneurship. Whether you’re a host or a fan of unique getaways, this episode offers inspiration and practical tips for standing out in hospitality.

Things we discussed in this episode:

• Coleman Davis’s transition from NYC creative director to West Texas short-term rental host.

• The creation and branding of Ghost Town Casitas as a cinematic, Instagram-worthy destination.

• The importance of storytelling, design, and professional photography in hospitality.

• Challenges and logistics of operating rentals in remote areas, including water and electricity.

• The impact of COVID-19 on travel trends and the rise of West Texas as a destination.

• The role of influencer marketing and partnerships in promoting unique stays.

• Balancing entrepreneurship with family life and time management strategies.

• The process of designing properties with photography and guest experience in mind.

• Navigating regulations and the legal landscape for short-term rentals in different locations.

• The value of automation, community, and networking in growing a successful rental business.

Get in touch with Coleman:

Facebook - ⁠⁠⁠⁠⁠https://www.facebook.com/GhostTownCasitas/⁠

Instagram - ⁠⁠⁠⁠https://www.instagram.com/ghosttowncasitas/⁠

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.ghosttowncasitas.com/⁠

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #HospitalityDesign #BrandStorytelling #WestTexas #EntrepreneurLife #VacationRental #InstaWorthy #RemoteWork #InfluencerMarketing #FamilyBusiness

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 leave your 9–5 and build a successful short-term rental business on Cape Cod? 🌊🏡

In this episode, we sit down with Matt Cutler, who made the bold leap from a traditional W2 career to creating a thriving STR operation in one of New England’s most iconic vacation destinations. Matt pulls back the curtain on the emotional and financial realities of leaving corporate life, what it’s like to manage properties in a seasonal market, and why guest experience is everything. He also shares how he builds strong relationships with property owners, attracts repeat guests, and invests in the amenities that actually move the needle.

Whether you’re dreaming of your first rental or scaling a growing portfolio, this episode is packed with hard-earned insights and honest advice you won’t want to miss.

🎧 Hit play and get inspired to take your next big step.

Things we discussed in this episode:

• Transitioning from a W2 job to full-time real estate investing and short-term rental management.

• The journey of starting with a duplex outside Boston and expanding to Cape Cod and St. Augustine Beach.

• The importance of building relationships with property owners and setting clear expectations.

• The unique characteristics and predictability of the Cape Cod vacation rental market.

• Strategies for managing seasonality and filling off-season vacancies, including midterm rentals and platforms like Furnish Finder.

• The role of amenities and design in attracting guests, especially during shoulder seasons.

• Approaches to handling repeat guests and the challenges of aligning pricing with market rates.

• Differentiating as a property manager by focusing on guest experience and continuous improvement.

• Navigating owner-occupied versus investment properties and managing owner expectations.

• The challenges and rewards of entrepreneurship, including scaling the business and deciding when to hire additional help.

Get in touch with Matt:

Facebook - ⁠⁠⁠⁠https://www.facebook.com/beacondestinations⁠

Instagram - ⁠⁠⁠https://www.instagram.com/beacondestinations/#⁠

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.beacondestinationsstr.com/⁠

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #CapeCod #VacationRentals #Entrepreneurship #PropertyManagement #GuestExperience #MidTermRentals #DirectBooking #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 does it take to walk away from a high-paying corporate job and build a 50+ property short-term rental empire?

In this episode, I sit down with real estate investor and coach Matt McCall Stillman, along with attorney and legal expert Rory Gill, for a powerful conversation about what it really takes to succeed in the short-term rental world.

We dive into Matt’s journey—how he went from corporate burnout to STR powerhouse—and unpack the mindset shifts, calculated risks, and coaching that helped him scale. Along the way, we explore market trends, legal must-knows for investors, and why having local knowledge and legal support can make or break your success.

Whether you're managing your first listing or looking to grow your portfolio, this episode is full of raw insight, practical advice, and stories that will inspire and inform your next move.

👉 Don't forget to like, subscribe, and hit the bell for more STR success stories and tips!

Things we discussed in this episode:

• From Corporate to Real Estate: Matt's Bold Career Shift

• Why Mindset Matters in Entrepreneurship

• How Matt Scaled to 50+ Properties

• The Real Value of a Great Coach in Real Estate

• STR Market Trends: Design, Amenities & Regulations

• Seasonality & Revenue Strategy in Short-Term Rentals

• Local vs. Remote Investing: What Works Best?

• Lessons Learned from Hotel Ownership

• Legal Must-Knows for STR Investors

• Top Advice for First-Time STR Buyers

Get in touch with Matt:

Facebook - ⁠⁠https://www.facebook.com/MyBrokerMatt

Instagram - ⁠https://www.linkedin.com/in/mybrokermatt/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://go.thestrlegend.com/mastermind

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbInvestment #RealEstateSuccess #PropertyInvesting #STRStrategy #OffMarketDeals #AirbnbTips #RealEstateCoaching #PassiveIncome #PropertyManagement

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 what it really takes to pack up your life, move to a new city, and build a short-term rental business from scratch?

In this episode, We sat down with my friend Chachi Horgan — a former real estate agent from Maine who took a leap, moved to Florida, and built Roam Ready Vacation Rentals, scaling to 11 properties in less than two years.

We talk about everything — the mindset it took to start over, the power of building a solid network, what it’s like navigating a new market, and why learning to delegate is absolutely critical if you want to grow. Chachi also shares how coaching lacrosse and a love of personal development shaped how he runs his business today.

If you're thinking about starting a vacation rental business — or scaling the one you already have — this one's loaded with real stories, raw insights, and some seriously motivating perspective.

Things we discussed in this episode:

• Chachi's transition from real estate agent to short-term rental business owner in Florida

• The importance of networking and building relationships in a new community

• Strategies for analyzing and selecting properties using tools like AirDNA and PriceLabs

• The challenges of scaling a business and delegating tasks effectively

• Mindset development and personal growth through reading business and self-help books

• Dealing with seasonality in short-term rental markets

• The value of having a growth mindset and continuous improvement

• Expanding business operations across multiple markets (Florida and Maine)

• The role of virtual assistants and team members in business growth

• Leveraging coaching and athletic experience in developing business skills and mindset training

Get in touch with Chachi:

Facebook - ⁠https://www.facebook.com/chachi.horgan

Instagram - https://www.instagram.com/the_realestate_chachi/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://roamreadyvacationrentals.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbInvestment #RealEstateSuccess #PropertyInvesting #STRStrategy #OffMarketDeals #AirbnbTips #RealEstateCoaching #PassiveIncome #PropertyManagement

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 a side hustle built on friendship and a love of travel become something bigger?

Join Jason Muth, Rory Gill, and Ethan Sobel as they share the real story behind Prideaway Stays, their co-hosting venture in Provincetown. From a family dream of owning a Cape home to building a guest-first rental brand, this episode dives into the heart of short-term rental hosting.

Discover how they scaled their business while staying personal, built community connections, and turned passion into purpose.

🎧 A must-listen for anyone curious about real estate, entrepreneurship, or the power of partnership.

Things we discussed in this episode:

• Ethan’s Cape Cod Investment Origin

• Founding Pride Away Stays

• Emotional Drivers in STR Investing

• Scaling with a Personal Touch

• Building Trust with Owners & Guests

• Seasonality & Slow Growth in Ptown

• Diverse Team & Strong Systems

• Friendship to Business Partnership

• STRs as Income & Fulfillment

• Community-Focused Hosting Mission

Get in touch with Fouad:

Facebook - https://www.facebook.com/prideawaystays/

Linkedin - ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/98969932/admin/dashboard/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://prideawaystays.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #PridewayStays #ProvincetownRentals #STRBusiness #VacationRentals #GayOwnedBusiness #AirbnbTips #TravelCommunity #EntrepreneurJourney

Follow Us!

Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!

Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide.

SmartStay Show ⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠ and⁠⁠⁠⁠⁠⁠⁠⁠⁠ YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠

Prideaway Stays ⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠

Hospitality.FM

SmartStay Show is part of⁠⁠⁠⁠⁠⁠⁠⁠⁠ Hospitality.FM⁠⁠⁠⁠⁠⁠⁠⁠⁠, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!

What if your best-performing Airbnb was sitting just a mile away—and you almost missed it?

In this episode, we talk with Jeremy Beland, a real estate investor who made the leap from wholesaling to building a killer short-term rental portfolio in Port St. Lucie, Florida. He shares how one overlooked pocket became home to his top-performing property—and why hyper-local strategy matters more than most people realize.

Jeremy and his wife pull back the curtain on what it really takes to succeed in the Airbnb space. From rehabbing a rundown house to creating a five-star guest experience, they walk through the messy, unglamorous, and essential parts of running short-term rentals like a real business.

Whether you’re already hosting or just thinking about it, this one’s packed with real-world advice, hard-earned lessons, and a few laughs along the way.

Things we discussed in this episode:

• Jeremy’s shift from off-market deals to short-term rentals

• Why location—down to a one-mile radius—matters

• The real challenges of furnishing from scratch

• Building a strong local cleaning and maintenance team

• Treating STRs like a business, not a side hustle

• Smart guest screening to protect your property

• How reviews impact long-term success

• Jeremy’s REI Freedom program on off-market strategies

• Long-term wealth potential of STR investments

• The hospitality mindset behind a top-tier Airbnb

Get in touch with Jeremy:

Linkedin - ⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jeremy-beland-164b8913/

Facebook - ⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/groups/795700988329071/media

Instagram - ⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/jeremybeland_/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbInvestment #RealEstateSuccess #PropertyInvesting #STRStrategy #OffMarketDeals #AirbnbTips #RealEstateCoaching #PassiveIncome #PropertyManagement

Follow Us!

Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!

Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide.

SmartStay Show ⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠ and⁠⁠⁠⁠⁠⁠⁠ YouTube⁠⁠⁠⁠⁠⁠⁠

Prideaway Stays ⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠

Hospitality.FM

SmartStay Show is part of⁠⁠⁠⁠⁠⁠⁠ Hospitality.FM⁠⁠⁠⁠⁠⁠⁠, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!

What if your real estate business was designed to serve your life — not run it?

In this episode, we chat with Fouad Bazzi, a former banker who left the corporate world to build a thriving short-term rental business centered around freedom, family, and purpose. He shares how he scaled his operations, mentors the next generation (including his own kids), and shifted from chasing work-life balance to creating true work-life unity.

This isn’t just about real estate — it’s about building a values-driven business that aligns with the life you want. Whether you're an investor or just curious about the space, this conversation will challenge and inspire you. Hit play and get ready to rethink success.

Things we discussed in this episode:

• Fouad’s shift from banking to STR for time and financial freedom

• Goal-driven real estate strategies over social media trends

• Rebranding from Crescent Retreats to The Owner Hosts

• Involving family in staging and business learning

• Building a global team with specialized virtual assistants

• Health and fitness as pillars of entrepreneurial success

• STR Cohort: action-based consulting and peer learning

• Embracing “work-life unity” over balance

• Tax strategies and real estate for high-income earners

• Creating sellable, legacy-driven businesses

Get in touch with Fouad:

Facebook - ⁠⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/foubazzi/

Linkedin - ⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/fouad-bazzi-4415973/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠https://www.fouadbazzi.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #OpportunityZones #ShortTermRentals #EntrepreneurLife #FamilyBusiness #FinancialFreedom #AirbnbHost #BusinessMindset #PropertyManagement #EntrepreneurialFamily #WealthBuilding

Follow Us!

Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!

Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide.

SmartStay Show ⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠ and⁠⁠⁠⁠⁠⁠⁠⁠ YouTube⁠⁠⁠⁠⁠⁠⁠⁠

Prideaway Stays ⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠

Hospitality.FM

SmartStay Show is part of⁠⁠⁠⁠⁠⁠⁠⁠ Hospitality.FM⁠⁠⁠⁠⁠⁠⁠⁠, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!

What if your next real estate deal could help you eliminate capital gains taxes—while building a thriving short-term rental business?

In this episode, tax strategist Ashley Tison dives into the powerful world of Opportunity Zones and how investors can use them to unlock huge tax advantages. These zones aren't just distressed areas—they include beachfront properties, university towns, and booming urban districts.

Ashley explains how to transform a property in an Opportunity Zone, count even furniture and equipment as improvements, and potentially walk away from the investment completely tax-free after 10 years. But there’s a deadline: you’ll need a capital gain by December 31, 2026, and an active business within the zone.

Whether you're eyeing a downtown mixed-use building or a waterfront rental community, this episode shows how to invest with strategy, purpose, and serious long-term upside.

Things we discussed in this episode:

• Opportunity Zones: Created by the 2017 Tax Cuts and Jobs Act

• Defer and Eliminate Capital Gains by Holding for 10 Years

• Short-Term Rentals Qualify—Including Furnishings and Equipment

• Act Fast: Final Investment Deadline is December 31, 2026

• University Areas Offer Prime OZ Investment Potential

• You Must Actively Operate a Business—Not Just Use Personally

• Mixed-Use Buildings Are Ideal for OZ Strategies

• Meet the ‘Substantial Improvement’ Rule to Qualify

• Use SBA Loans to Fund Mixed-Use OZ Projects

• Invest Gains from Stocks, Real Estate, or Other Appreciated Assets

Get in touch with Ashley:

Facebook - ⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/ozpros

Linkedin - ⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/ozproscom/

Website - ⁠⁠⁠⁠⁠⁠⁠https://ozpros.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #OpportunityZones #ShortTermRentals #TaxStrategy #WealthBuilding #TaxSavings #PropertyInvestment #AirbnbInvesting #PassiveIncome #InvestmentTips

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!