Welcome to the SmartStay Show, your go-to podcast for mastering Short-Term Rentals on Airbnb, Vrbo, and beyond. For more Airbnb tips, visit smartstayshow.com and smartstaycoaching.com.
Hosted by 30-time Airbnb Superhost Jason Muth and Real Estate Attorney Rory Gill, we equip you with the tools to launch, manage, and optimize your vacation rental like a pro.
Unlike other shows, we specifically cater to owners of small-but-mighty portfolios who self-manage their properties. Each episode delivers expert insights, legal tips, and proven strategies from successful hosts across the U.S. Whether you’re buying your first property, improving your listing, or looking to stay ahead of the competition, we offer actionable advice and real-life stories to help you thrive.
From pricing strategies to guest communication, we provide the playbook to turn your property into a top-performing rental. Subscribe now and unlock your rental’s full potential with the SmartStay Show!
Welcome to the SmartStay Show, your go-to podcast for mastering Short-Term Rentals on Airbnb, Vrbo, and beyond. For more Airbnb tips, visit smartstayshow.com and smartstaycoaching.com.
Hosted by 30-time Airbnb Superhost Jason Muth and Real Estate Attorney Rory Gill, we equip you with the tools to launch, manage, and optimize your vacation rental like a pro.
Unlike other shows, we specifically cater to owners of small-but-mighty portfolios who self-manage their properties. Each episode delivers expert insights, legal tips, and proven strategies from successful hosts across the U.S. Whether you’re buying your first property, improving your listing, or looking to stay ahead of the competition, we offer actionable advice and real-life stories to help you thrive.
From pricing strategies to guest communication, we provide the playbook to turn your property into a top-performing rental. Subscribe now and unlock your rental’s full potential with the SmartStay Show!
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:
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:
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:
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:
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:
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:
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:
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:
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!
What Happens When Your Airbnb Becomes a Disaster?
Join us as we sit down with Andy Gurczak, a seasoned public adjuster and new short-term rental owner, to explore the often-overlooked world of insurance claims for vacation rentals.
In this eye-opening episode, Andy reveals insider tips on protecting your property and why your standard homeowner's insurance policy might not have your back when you're hosting on platforms like Airbnb. From how one plumber's report can make or break a claim, to the vital importance of documenting everything—from receipts to photos—Andy shares his expert advice.
Drawing on his personal experience as a new short-term rental owner, Andy also talks about the real challenges of setting up and managing a rental property. Plus, he provides his direct contact info for listeners seeking tailored insurance advice, making this episode an invaluable resource for anyone serious about safeguarding their investment.
Whether you're a seasoned host or just starting out, this episode offers practical wisdom on navigating the complexities of insurance and avoiding potential pitfalls in the vacation rental world. Don't miss it!
Things we discussed in this episode:
Why you need specialized insurance for short-term rentals like Airbnb
How public adjusters fight for your claim and maximize payouts
The importance of documenting everything—photos, receipts, inventory
Hidden gaps in standard homeowner’s policies for rental properties
Real challenges of setting up and managing a new short-term rental
Why loss of income coverage is a must for vacation rental owners
How to simplify property management and enhance guest experience
Key policy details and exclusions every host should know
Building referral networks with insurance pros and mitigation teams
Get in touch with Andy:
LinkedIn - https://www.linkedin.com/in/andy-gurczak-528b9b64/
Facebook - https://www.facebook.com/Andy.Gurczak
Website - https://allcityadjusting.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #AirbnbInsurance #PropertyInvestment #InsuranceClaims #RentalPropertyTips #PublicAdjuster #VacationRentalOwners #PropertyProtection #STRBusiness
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!
Did you know your short-term rental could be a powerful tax-saving machine?
In this episode, We sit down with Sean Graham—CPA, real estate investor, and cost segregation expert—to uncover how vacation rental owners can legally slash their tax bills using smart depreciation strategies.
From bonus depreciation and the short-term rental loophole to material participation rules, Sean breaks down complex tax concepts in a way that actually makes sense (yes, really!). You'll learn how the IRS actually encourages real estate investors to succeed—and how a simple cost segregation study could save you thousands.
Whether you’re a high-income earner or just getting started in the rental game, this episode is packed with actionable insights to help you keep more money in your pocket and reinvest with confidence.
Grab a pen. Take notes. This could change the way you invest.
Things we discussed in this episode:
Cost Segregation: Accelerates depreciation by breaking property into components with 5-, 7-, or 15-year lifespans instead of the standard 27.5 or 39 years.
Bonus Depreciation: Allows large first-year write-offs for property improvements; phasing down to 40% in 2025.
Short-Term Rental Loophole: Treats short-term rentals as active businesses, enabling high earners to offset W-2 income with depreciation.
Material Participation: To claim active status, owners must spend 100+ hours and more time than anyone else on the property.
Real Estate Professional Status (REPS): Requires 750+ hours annually in real estate to treat rental losses as active and offset other income.
Tax Deferral: Investors can defer taxes by reinvesting gains and passing properties through inheritance with a step-up in basis.
IRS Incentives: The IRS offers generous depreciation and tax breaks to encourage real estate investment.
Cost Segregation Process: Engineering studies allocate costs to shorter-life components for faster depreciation.
Co-Hosting Impacts: Using third-party managers can affect an owner’s ability to meet material participation rules.
Eligible Properties: Cost segregation works best for high-value short-term and long-term rentals with substantial improvements.
Get in touch with Sean:
Facebook - https://www.facebook.com/people/Maven-Cost-Segregation-Tax-Advisors/61570153671981/ LinkedIn - https://www.linkedin.com/company/mavencostseg/
Instagram - https://www.instagram.com/mavencostseg/
Website - https://mavencostseg.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #TaxStrategy #CostSegregation #BonusDepreciation #TaxSavings #RentalProperty #InvestmentTips #PassiveIncome #RealEstateWealth
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!
Are you ready to find your next cash-flowing short-term rental property — and actually know it’s a winner before you buy?
In this episode, We sit down with John Bianchi, the self-proclaimed "Airbnb Data Guy," who's helped uncover over 200 profitable STR properties. John pulls back the curtain on how to spot the best markets, why understanding local regulations is critical, and how effective marketing can make or break your rental’s success.
You'll learn John's two-step method for market selection, dive into real-world property analysis (including a live review of Jason and Rory's property in Laconia, New Hampshire), and get practical tips like the "20% rule" and how to maximize your property's potential with strategic photography.
Whether you're investing your first dollar or expanding your growing portfolio, John's data-driven insights and no-nonsense advice will give you the edge to make smarter, more profitable decisions. Get ready for a deep-dive that's packed with actionable strategies you can use right now!
Things we discussed in this episode:
Get in touch with John:
LinkedIn - https://www.linkedin.com/in/john-bianchi/
Instagram - https://www.instagram.com/theairbnbdataguy/
Website - https://strsearch.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #STRInvesting #AirbnbDataGuy #ShortTermRental #RealEstateInvestment #PropertyInvesting #PassiveIncome #RentalMarkets #InvestmentStrategy #RealEstateData #STRTips
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!
Are you putting all your hosting eggs in the Airbnb basket? What if there's a smarter way to grow your short-term rental business?
In this eye-opening episode, we sit down with Mark Simpson, founder of Boostly and one of the world’s top experts in direct booking strategies. From running a family farm stay to becoming a global authority on short-term rental marketing, Mark’s journey is as inspiring as it is informative.
Discover why relying solely on one platform can be a risky move—and how you can take back control. Mark shares powerful, practical tactics for boosting direct bookings, defining your ideal guest avatar, and using tools like AI and ChatGPT to optimize your listings and guest communication.
Whether you're just starting out or managing a portfolio of properties, this episode is packed with golden nuggets that will help you build a resilient, profitable business that doesn’t depend on just one booking site. Don't miss this one—Mark’s insights might just be the game-changer your hosting journey needs.
Facebook - https://www.facebook.com/BoostlyUk/
Instagram - https://www.instagram.com/boostlyuk/
Linkedin - https://www.linkedin.com/in/mrmarksimpson/
Website - https://boostly.co.uk/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #DirectBookings #ShortTermRental #AirbnbStrategy #HostTips #TravelIndustry #AIinHospitality #MarketingForHosts #PropertyManagement #BoostlyMarketing #TechForHosts
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!
Are you leaving money on the table with your short-term rental?
In this episode, We sit down with CPA and tax strategist Anne Gannon to uncover the often-overlooked financial advantages of real estate investing. Anne simplifies complex tax topics and reveals how savvy investors use short-term rentals not just for income—but to build long-term wealth.
From depreciation strategies to smart tax planning, you'll learn how to make the most of your property and use the tax code to your advantage. Whether you're a seasoned investor or just getting started, this episode is packed with actionable insights that could transform your financial future.
Find out why Anne says her happiest retired clients are real estate investors—and how you can follow in their footsteps with smart, strategic moves. Don’t miss this wealth-building masterclass!
Facebook - https://www.facebook.com/profile.php?id=100095441858241
Instagram - https://www.youtube.com/@AcceleratorMethod
Linkedin - https://www.linkedin.com/in/anne-gannon-529107148/
Website - https://www.thelargogroup.com/About
https://www.accelerator-method.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #TaxStrategy #PassiveIncome #TaxPlanning #RealEstateWealth #InvestmentTips #PropertyInvestment #FinancialFreedom #STRTaxBenefits
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 vacation rental came with VIP treatment?"
Dive into the world of luxury short-term rentals with Kevin Duran, founder of JKW Vacation Club. In this episode, we explore a game-changing approach to vacation stays—one that goes beyond traditional Airbnb bookings.
Kevin shares how his innovative membership model offers travelers a full concierge experience, including airport shuttles, grocery delivery, and exclusive local experiences. For property owners, JKW provides a powerful marketing and optimization strategy to fill calendars and create meaningful guest connections.
With a background in sales and tech, Kevin is building a network of high-end properties across different locations, focusing on unforgettable, personalized travel experiences. Whether you're a property owner looking to maximize revenue or a traveler seeking VIP service, this episode is packed with insights into the future of short-term rentals and hospitality.
Facebook - https://www.facebook.com/JKWVacation
Website - https://jkwvacationclub.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #LuxuryTravel #VacationClub #TravelExperiences #PropertyInvestment #HospitalityInnovation #AIinTravel #ConciergeService #TravelTech #STRBusiness
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!
