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/YHAMLLCWebsite - https://yham.host/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Hospitality #AirbnbHost #GuestExperience #RentalBusiness #STRSuccess #HostTips #VacationRental #HospitalityTechFollow 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 YouTubePrideaway Stays Website and on Facebook and LinkedInStraightforward Short-Term Rentals Website and on InstagramAttorney Rory Gill on LinkedInJason 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:The expanding demand for midterm rentals beyond travel nurses, including contractors, relocating families, and corporate workers.The importance of understanding your local “micro market” to determine midterm rental potential.Strategies for hosts to balance short-term and midterm rentals seasonally for optimal occupancy.Guest expectations for midterm stays, such as extra linens, pet-friendliness, and practical amenities.The impact of booking platforms and fees, and how Furnished Finder’s model differs from Airbnb/VRBO.How occupancy taxes vary by state and the implications for longer stays.The necessity of having proper insurance coverage tailored to midterm rentals.Trends in who is hosting midterm rentals, from individual owners to professional managers.The value of screening midterm tenants, including credit, criminal, and eviction checks.Tips for analyzing market demand using tools like Furnished Finder’s stats page and networking with other hosts.Get in touch with Katie:Instagram - https://www.instagram.com/furnishedfinder/Facebook - https://www.facebook.com/FURNISHEDFINDERWebsite - https://www.furnishedfinder.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #MidtermRentals #FurnishedFinder #RentalProperty #PropertyManagement #TravelNurseHousing #CorporateHousing #HostTips #SmartStayFollow 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 YouTubePrideaway Stays Website and on Facebook and LinkedInStraightforward Short-Term Rentals Website and on InstagramAttorney Rory Gill on LinkedInJason 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:Kareem Sanjaghi’s journey from mortgage officer to full-time musician and real estate investor.The story of Kareem becoming the first client of Pride Away Stays and how that partnership began.Details about Kareem’s Provincetown beachfront condo, including its location, size, and unique features.The importance of location and seasonality in maximizing short-term rental revenue in Provincetown.Overcoming challenges with previous property management and improving guest experience.Navigating HOA dynamics and the importance of communication with other unit owners.Handling unexpected issues (e.g., construction, alarms, maintenance) and setting guest expectations.The financial benefits of real estate ownership, including cash flow and tax advantages.Kareem’s personal growth, balancing music and real estate, and his transition to pursuing music full-time.The value of strong partnerships, open communication, and learning from both successes and setbacks in property management.Get in touch with Kareem:Instagram - https://www.instagram.com/thekareemofthecrop/Facebook - https://www.facebook.com/thekareemofthecropWebsite - https://www.kareemdrums.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Provincetown #CapeCod #PropertyManagement #Entrepreneurship #VacationRental #MusicianLife #SmartInvesting #PersonalGrowthFollow 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 YouTubePrideaway Stays Website and on Facebook and LinkedInStraightforward Short-Term Rentals Website and on InstagramAttorney Rory Gill on LinkedInJason 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/togetherevacationrentalsWebsite - https://togetherevacationrentals.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals AirbnbHost #PropertyManagement #Notion #BusinessSystems #VacationRental #Automation #TeamBuilding #HospitalityIndustry #ProductivityHacksFollow 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 YouTubePrideaway Stays Website and on Facebook and LinkedInStraightforward Short-Term Rentals Website and on InstagramAttorney Rory Gill on LinkedInJason 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 #GuestExperienceFollow 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 YouTubePrideaway Stays Website and on Facebook and LinkedInStraightforward Short-Term Rentals Website and on InstagramAttorney Rory Gill on LinkedInJason 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.comLinkedIn - https://www.linkedin.com/in/jacob-r-martinWebsite - https://www.lodgeandleisure.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Entrepreneurship #VacationRentals #PropertyManagement #CoHosting #FinancialFreedom #BusinessGrowth #AirbnbHost #InvestSmartFollow 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 YouTubePrideaway Stays Website and on Facebook and LinkedInStraightforward Short-Term Rentals Website and on InstagramAttorney Rory Gill on LinkedInJason 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/ARealGreen123Instagram - https://www.instagram.com/arealgreen/Website - https://adriennegreen.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #VirtualAssistants #PropertyManagement #BusinessSystems #Automation #TimeFreedom #Entrepreneurship #AIinBusiness #SOPsFollow 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 YouTubePrideaway Stays Website and on Facebook and LinkedInStraightforward Short-Term Rentals Website and on InstagramAttorney Rory Gill on LinkedInJason 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 #FamilyBusinessFollow 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 YouTubePrideaway Stays Website and on Facebook and LinkedInStraightforward Short-Term Rentals Website and on InstagramAttorney Rory Gill on LinkedInJason 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/beacondestinationsInstagram - https://www.instagram.com/beacondestinations/#Website - https://www.beacondestinationsstr.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #CapeCod #VacationRentals #Entrepreneurship #PropertyManagement #GuestExperience #MidTermRentals #DirectBooking #BusinessGrowthFollow 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 YouTubePrideaway Stays Website and on Facebook and LinkedInStraightforward Short-Term Rentals Website and on InstagramAttorney Rory Gill on LinkedInJason 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!
What does it take to turn a small real estate side hustle into a global corporate housing empire? In this episode, we sit down with Gary Brown and his son Ken Brown of Furnished Quarters to explore their incredible journey from NYC real estate investors to international leaders in corporate housing. With roots in their family’s furniture business and a knack for strategic growth, this father-and-son duo has helped shape the company’s expansion from a few furnished apartments in Manhattan to a global portfolio of 1,000+ units. They break down how corporate housing fills a unique niche between hotels and Airbnb—offering professionals fully furnished apartments for 30 days or longer—and explain what truly sets their approach apart when it comes to design, guest experience, and client retention. From navigating post-COVID market shifts to scaling operations across continents, Gary and Ken share hard-earned insights that every entrepreneur in hospitality, real estate, or short-term rentals needs to hear. Whether you're new to the space or ready to scale, this episode is packed with lessons in adaptability, service, and smart growth. Things we discussed in this episode: Fully furnished apartments for 30+ day stays Furnished Quarters was founded in the 1980s by brothers Gary and Steve Brown This episode features Gary and his son, Ken Brown Rooted in real estate and family furniture expertise Serves corporate relocations, interns, and families in transition COVID-19 reshaped demand for space and flexibility Properties in business hubs and family-friendly neighborhoods 24/7 high-touch customer service and quick issue resolution Operates 1,000+ units across multiple countries Neutral, locally inspired interior design for broad appeal Keys to scaling: great people, flexibility, and consistent service Get in touch with Ken and Gary: Linkedin Ken - https://www.linkedin.com/in/ken-brown-89555035/ Linkedin Gary - https://www.linkedin.com/in/gary-brown-b324512/ Website - https://www.furnishedquarters.com/meet-the-team #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #HospitalityTrends #BusinessTravel #PropertyManagement #FurnishedQuarters #RealEstateStrategy #TravelAccommodations #EntrepreneurialJourney 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 does it take to grow from managing one small rental to overseeing 40+ short-term properties in just seven years? In this episode, we sit down with Alex Steeg, a short-term rental entrepreneur who's built a thriving business across Boston’s North Shore. His journey is nothing short of inspiring—from starting with a modest two-family property to managing a diverse and growing portfolio. Alex shares how his early career in residential advising unexpectedly prepared him for the world of property management. Alongside his wife Rachel, he began with traditional long-term rentals before discovering the game-changing potential of short-term stays—unlocking significantly higher cash flow and more flexibility. Today, Alex manages everything from cozy studios to expansive 22-acre estates, and he’s in the middle of renovating a 10-unit inn in Ipswich. He dives into the strategies that helped him scale, the lessons learned along the way, and how intentional planning and adaptability have fueled his success. Whether you’re just starting out or looking to grow your own STR business, this episode is packed with real-world insights and inspiration. Things we discussed in this episode: Alex Steeg's career transition from seminary and residential advising to short-term rental management The founding of Shoreway Management by Alex and his wife Rachel, growing to over 40 properties Their strategic approach to real estate investing, starting with a two-family property in 2018 The game-changing impact of short-term rentals on their cash flow and business growth Alex's recent purchase and renovation of the 10-unit Ipswich Inn, managing a complex commercial property renovation The importance of complementary skills in a spouse-run business, with Rachel handling operations and Alex focusing on client relations Their geographical focus on managing properties along Boston's North Shore, including towns like Marblehead, Salem, and Gloucester Being named a top-rated short-term rental management company by AirDNA The challenges and benefits of working together as a married couple in a business Their involvement with Smart Stay coaching and helping other aspiring real estate investors and short-term rental operators Get in touch with Alex: Facebook - https://www.facebook.com/alex.steeg86/ Instagram - https://www.instagram.com/alexsteeg/ Website - https://www.shorewaymgmt.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #EntrepreneurJourney #PropertyInvestment #BostonRealEstate #BusinessCouple #RentalManagement #SmartStayCoaching #RealEstateSuccess 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!
Want to turn your vacation rental into an unforgettable adventure that guests can’t stop talking about? In this episode of the SmartStay Show, we sit down with Rachel DeSantis — the mastermind behind QR Clue, a groundbreaking in-home escape game that transforms ordinary short-term rentals into immersive, puzzle-filled experiences! Imagine your guests stepping into a thrilling story where they solve clever puzzles, uncover hidden clues, and win prizes — all through simple, strategically placed QR codes. Rachel shares how this innovative concept not only makes stays wildly fun but also skyrockets your five-star reviews and booking rates. With quick three-minute setups and fully customizable storylines, QR Clue offers a fresh, tech-savvy way to stand out in a crowded rental market and create lasting memories for your guests. If you’re a host looking to boost your rental’s appeal and provide an experience guests rave about, this episode is packed with insights you don’t want to miss. Press play and discover how storytelling and technology can literally change the game for your short-term rental business! Things we discussed in this episode: Transforms vacation rentals into escape room-style adventures. Guests scan hidden QR codes to solve puzzles and follow a storyline. Takes 2–3 hours to complete; guests can pause and resume anytime. Setup takes just 3 minutes with a ready-to-go kit for cleaners. Hosts can promote it in listings to attract more bookings. Collects guest names and emails at game start. Leads to more five-star reviews and detailed feedback. Seasonal themes like Halloween and Christmas coming soon. Featured at VR Nation in April with a live demo. Designed to create unforgettable stays with minimal effort for hosts. Get in touch with Rachel: Facebook - https://www.facebook.com/qrclue/ Instagram - https://www.instagram.com/getqrclue/ Website - https://www.qrclue.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #QRClue #ShortTermRental #AirbnbExperience #TravelTech #HostTips #VacationRental #GuestExperience #EscapeRoom #HospitalityInnovation #STRMarketing 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!
Feeling “equity rich” but still cash strapped? You’re not alone—and there’s a smarter way to break free. In this eye-opening episode, We sit down with Certified Financial Planner Alan Franks to explore how real estate investors can unlock hidden capital, boost returns, and build lasting wealth. Alan shares powerful strategies for using tools like home equity lines of credit and securities-based lending to access cash without selling off valuable assets. He also sheds light on how the post-COVID real estate market has shifted—and how savvy investors are adapting. With clarity, humor, and real-world examples, Alan unpacks complex financial concepts and shows how to take advantage of tax-saving opportunities, diversify your portfolio, and rethink the way you use leverage. Whether you're managing multiple short-term rentals or just starting out, this episode will help you think bigger, plan smarter, and make your money work harder. It’s the conversation every real estate investor needs—but probably never had. Ready to reimagine your investment strategy? Hit play and discover what’s possible. Things we discussed in this episode: Use HELOCs to access cash for investment opportunities. Diversify across real estate and traditional assets. Borrow against securities to unlock investment capital. Leverage tax benefits like bonus depreciation and RE pro status. Adapt to STR shifts post-COVID in supply and demand. Prioritize appreciation, even with low initial cash flow. Use credit lines to scale real estate portfolios. Plan for high rates and increased competition. Factor opportunity cost into investment decisions. Balance investments across real estate, retirement, and taxable accounts. Get in touch with Alan: LinkedIn - https://www.linkedin.com/in/alanfranks/ Instagram - https://www.instagram.com/frankly_financial/ Website - https://www.empowered-money.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #WealthBuilding #FinancialPlanning #ShortTermRentals #InvestmentStrategy #PassiveIncome #RealEstateWealth #FinancialFreedom #PropertyInvestment #TaxAdvantages 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 happens when a frustrated Airbnb host builds a tool to solve his own problem—and ends up launching one of the most influential platforms in short-term rentals? In this episode, we sit down with Pierre-Camille Hamana, CEO and founder of Hospitable, to explore his surprising journey from law school dropout to tech entrepreneur. What began as a simple solution to automate guest messaging for his own rental has grown into a powerhouse property management platform supporting tens of thousands of listings across the globe. Pierre shares the real story behind Hospitable’s evolution—from a basic tool for solo hosts to a full-fledged system tackling everything from platform integration to direct bookings. We dive into the complexities of building software for hosts, the future of short-term rental automation, and why simplicity is the key to scaling. Whether you're a seasoned host, a budding entrepreneur, or just fascinated by startup journeys, this episode is packed with insight, inspiration, and behind-the-scenes moments from a founder who’s quietly reshaping the future of hospitality tech. Things we discussed in this episode: Founder’s Origin: Pierre Hamana began by renting out a room on Airbnb and built Hospitable to automate his own guest messaging. Early Focus: Designed for small hosts managing fewer than 7 properties. Direct Bookings: Built-in booking engine with ID checks, rental agreements, and deposit handling. OTA Integrations: Navigated complex relationships with platforms like Airbnb and Booking.com. Community Input: Product roadmap shaped by user forums and direct feedback. Support Culture: Globally distributed team known for fast, friendly help—often using memes. Vision: Exploring marketplace tools and STR property investments. Small Host Challenges: Tackled issues like payment processing and lack of support from traditional vendors. Platform Growth: Evolved from a messaging tool to an all-in-one host solution. Tech Democratization: Making powerful tools accessible to individual hosts and self-managers. Get in touch with Pierre: Facebook - https://www.facebook.com/20AD6664F78B17B8FED5 LinkedIn - https://www.linkedin.com/in/pchamana/ Instagram - https://www.instagram.com/pchamana/ Website - https://smartbnb.io/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #AirbnbTips #HostTech #PropertyManagement #TravelTech #EntrepreneurStory #DirectBookings #HostLife #HospitableSoftware #STRInnovation 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!