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

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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 - ⁠⁠⁠⁠⁠⁠[email protected]

LinkedIn - ⁠⁠⁠⁠⁠https://www.linkedin.com/in/jacob-r-martin

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

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Entrepreneurship #VacationRentals #PropertyManagement #CoHosting #FinancialFreedom #BusinessGrowth #AirbnbHost #InvestSmart

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

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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

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

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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

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

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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

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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

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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

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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

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

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

SmartStay Show ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Prideaway Stays ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Ever wonder what it really takes to 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:

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

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

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

SmartStay Show ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Prideaway Stays ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Straightforward Short-Term Rentals ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Attorney Rory Gill ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Jason Muth on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Hospitality.FM

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

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

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!