
SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips
by Airbnb Superhost Jason Muth + Rory Gill
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The Game-Changing Tax Move That Short-Term Rental Owners Overlook | Erik Oliver
Feb 24, 2026
37m 01s
From Fired to 31 Short-Term Rentals - MyBrokerMatt’s FULL Playbook | Matt McCall-Stillman
Jul 29, 2025
Unknown duration
How I Grew to 11 STRs in Months (Full Breakdown) | Chachi Horgan
Jul 22, 2025
Unknown duration
How Prideaway Stays Became Provincetown's #1 Airbnb Host | Ethan Sobel + Jason Muth
Jul 15, 2025
Unknown duration
After 450+ Real Estate Deals, I Finally Bought My 1st Airbnb (HERE'S WHY) | Jeremy Beland
Jul 8, 2025
Unknown duration
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 2/24/26 | ![]() The Game-Changing Tax Move That Short-Term Rental Owners Overlook | Erik Oliver✨ | tax strategycost segregation+3 | Erik Oliver | Maven Cost Segregation | — | tax billreal estate wealth+6 | — | 37m 01s | |
| 7/29/25 | ![]() From Fired to 31 Short-Term Rentals - MyBrokerMatt’s FULL Playbook | Matt McCall-Stillman | 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 | — | ||||||
| 7/22/25 | ![]() How I Grew to 11 STRs in Months (Full Breakdown) | Chachi Horgan | 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! | — | ||||||
| 7/15/25 | ![]() How Prideaway Stays Became Provincetown's #1 Airbnb Host | Ethan Sobel + Jason Muth | 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! | — | ||||||
| 7/8/25 | ![]() After 450+ Real Estate Deals, I Finally Bought My 1st Airbnb (HERE'S WHY) | Jeremy Beland | 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! | — | ||||||
| 7/1/25 | ![]() Airbnb, Family, and the Life I Never Had While Working a Corporate Job | Fouad Bazzi | 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! | — | ||||||
| 6/24/25 | ![]() The TRUTH About Airbnbs in Opportunity Zones (AMAZING Tax Benefits) | Ashley Tison | 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! | — | ||||||
| 6/17/25 | ![]() What Airbnb Hosts Don’t Realize About Furnished Rentals | Ken and Gary Brown | 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! | — | ||||||
| 6/10/25 | ![]() No Real Estate Background - 40+ STRs Later (HERE'S HOW) | Alex Steeg | 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! | — | ||||||
| 6/3/25 | ![]() WHAT? A Mystery Game That Lives Inside Your Airbnb?? | Rachel DeSantis | 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! | — | ||||||
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| 5/27/25 | ![]() NEVER Let Equity Sit Idle - Here's What Smart Real Estate Investors Do Instead | Alan Franks | 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! | — | ||||||
| 5/20/25 | ![]() Hosting Doesn’t Have to Be Chaotic (Hospitable’s Bold Fix) | Pierre-Camille Hamana | 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! | — | ||||||
| 5/13/25 | ![]() Insurance Claim Secrets That STR Hosts Need to Hear | Andy Gurczak | 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! | — | ||||||
| 5/6/25 | ![]() The Tax Strategy Airbnb Hosts Can’t Afford to Ignore | Sean Graham | 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! | — | ||||||
| 4/29/25 | ![]() Avoid the Biggest Mistakes in Airbnb Investing | John Bianchi | 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: John Bianchi’s two-step method for picking STR markets: check regulations and apply the 20% rule (annual revenue = 20% of purchase price). Why professional photography and marketing are key to standing out — especially when showcasing unique amenities and outdoor spaces. A deep dive into Jason and Rory’s Laconia, NH property: challenges with cash flow and market fit. The risks of buying in areas without clear STR regulations. How STRs offer cash flow, equity growth, and major tax benefits. Why you can’t fully trust AirDNA’s rentalizer tool — and how to do better comp analysis manually. John’s story: from building STR Search to helping identify 200+ profitable properties. How waterfront locations and standout features boost income. Diversifying investments: blending STRs with other vehicles. The deeper "why" behind STR investing: creating freedom and generational wealth. 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! | — | ||||||
| 4/22/25 | ![]() Confident Hosts Do This Differently - Boostly's Founder Mark Simpson Explains | 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.Things we discussed in this episode: The importance of diversifying booking platforms beyond Airbnb to reduce business risk Mark Simpson's background growing up in a family farm stay and how it shaped his hospitality perspective The concept of creating an ideal guest avatar to improve marketing and listing effectiveness Utilizing property management software (PMS) as a central "zone of truth" for booking management The role of AI tools like ChatGPT in improving listing copy, marketing, and operational efficiency Boostly's evolution from a training platform to offering website design and API integrations for direct bookings The shift in hospitality marketing from traditional newspaper ads to digital platforms and social media Strategies for getting more direct bookings, with a goal of reaching 65% direct booking rate The importance of becoming a brand ambassador for your location, not just focusing on property features How technology and AI are changing the short-term rental industry, with a focus on freeing up time for hosts and improving guest communication Get in touch with Mark: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 #TechForHostsFollow 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 LinkedInHospitality.FMSmartStay 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! | — | ||||||
| 4/15/25 | ![]() I Wish I Knew These Airbnb Tax Hacks Before We Bought | Anne Gannon | 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!Things we discussed in this episode: Short-term rentals offer unique tax benefits, often similar to those available to real estate professionals. Depreciation strategies—like cost segregation—can lead to major tax savings. Think long-term: a 5–10 year investment view helps maximize appreciation, equity, and wealth-building potential. COVID-19 underscored the importance of diversification—real estate proved to be a resilient asset. Learn the four-part test to qualify your STR as a business, including active involvement and risk. Short-term rentals have different tax treatments and greater operational complexity than long-term rentals. They can be part of a powerful retirement plan—especially when converting to a primary residence later. Cash-out refinancing and tapping into equity can offer tax-free liquidity. Understanding depreciation is key for scaling your portfolio strategically. Real estate offers long-term stability—Anne says her happiest retired clients are investors. Get in touch with Anne:Facebook - https://www.facebook.com/profile.php?id=100095441858241Instagram - https://www.youtube.com/@AcceleratorMethodLinkedin - 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 #STRTaxBenefitsFollow 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 LinkedInHospitality.FMSmartStay 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! | — | ||||||
| 4/8/25 | ![]() Luxury STR Hosts Are Using This Exclusive Booking Model! | Kevin Duran | "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.Things we discussed in this episode: Ski-Pass Style Membership – Members buy days to use across JKW’s luxury properties. VIP Concierge Services – Perks include shuttles, private chefs, massages, and curated experiences. Direct Booking Strategy – Virtual assistants prospect in Facebook groups to build a guest database. Premium Property Network – Partnering with owners to offer high-end, unique stays. Revenue Through Upsells – Bundling services with platforms like HostCo to boost earnings. Tech & PMS Challenges – Finding the right tools to streamline operations. AI & Sales Automation – Using Seamless.ai to target corporate clients. Luxury & Corporate Focus – Ideal for retreats, incentive programs, and tax-deductible stays. On-the-Ground Support – Hiring local managers to maintain brand standards. Revenue-Sharing for Owners – Fixed payouts when JKW members book their properties. Get in touch with Kevin:Facebook - https://www.facebook.com/JKWVacationWebsite - https://jkwvacationclub.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #LuxuryTravel #VacationClub #TravelExperiences #PropertyInvestment #HospitalityInnovation #AIinTravel #ConciergeService #TravelTech #STRBusinessFollow 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 LinkedInHospitality.FMSmartStay 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! | — | ||||||
| 4/1/25 | ![]() Why Making Your Airbnb ACCESSIBLE is a Smart Business Move! | Mrs. Schneider | Is Your Short-Term Rental Truly Welcoming to All Guests? In this must-listen episode, we sit down with Mrs. Schneider, an expert who understands the real challenges travelers with disabilities face. They uncover practical, budget-friendly ways to make your rental more accessible—like installing lever door handles, modifying bathrooms, and making small yet impactful changes.With nearly 70 million Americans living with disabilities, creating an inclusive space isn’t just the right thing to do—it’s a smart business move that sets you apart in a growing market.Whether you own one property or multiple rentals, you’ll walk away with actionable tips that can expand your guest pool and make a real difference.Tune in now and start making your rental truly welcoming for everyone! Things we discussed in this episode: Accessibility filters on Airbnb that allow hosts to highlight property features for guests with mobility challenges Practical modifications like using lever handles instead of knobs, which are similarly priced but much easier for people with limited hand mobility Bathroom accessibility improvements, including grab bars that double as towel racks, raised toilets, and shower benches The growing market of travelers with disabilities - currently 70 million Americans and projected to increase to 82 million in the next 20 years Legal considerations for hosts when claiming a property is "handicap friendly" or accessible Mrs. Schneider's innovative movable wheelchair tray designed to help people with disabilities eat and move more independently The importance of honest communication about a property's accessibility features and limitations Ramp and doorway width considerations for wheelchair accessibility Lighting and visibility improvements for guests with vision challenges, especially older travelers The broader impact of creating inclusive spaces that allow people with disabilities to travel and enjoy experiences with their families Get in touch with Mrs. Schneider:Facebook - https://www.facebook.com/profile.php?id=61567628681216Instagram - https://www.instagram.com/lessbarriers/Website - https://www.lessbarriers.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #AccessibleTravel #InclusiveHospitality #DisabilityTravel #AirbnbAccessibility #TravelForAll #AdaptiveHosting #Inclusive Tourism #AccessibleAirbnb #TravelInclusionFollow 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 LinkedInHospitality.FMSmartStay 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! | — | ||||||
| 3/25/25 | ![]() Betting on Yourself + Leaving a Lucrative Career for STRs (WAS IT WORTH IT?) | Payton Cummings | Would You Quit Your 9-to-5 to Build a Short-Term Rental Empire? Payton Cummings did exactly that—leaving behind a steady paycheck to scale a thriving 17-property short-term rental business! In this episode, she shares her journey from corporate consulting to full-time entrepreneurship, the mindset shifts that made it possible, and how community and strategy helped her think bigger. If you're dreaming of turning your side hustle into a sustainable business, this episode is packed with real insights and actionable advice you won’t want to miss! Things we discussed in this episode: Peyton's transition from a W2 management consulting job to full-time short-term rental entrepreneurship The importance of joining entrepreneurial communities like STR Secrets for networking and mindset growth Financial planning and considerations before leaving a steady job, including healthcare and income sustainability Building and scaling a short-term rental business from 3 personal properties to 17 co-hosted properties The challenges of delegating guest communication and learning to trust a virtual assistant team Strategies for local networking, including joining BNI groups and connecting with local developers and investors The value of investing time in personal mindset development and strategic business planning Real estate professional tax status and potential tax benefits for full-time real estate entrepreneurs Maintaining personal relationships and friendships while growing a business, especially as an entrepreneur The process of automating guest communications while still maintaining quality customer service and oversight . Get in touch with Payton: Facebook - https://www.facebook.com/payton.young.7Instagram - https://www.instagram.com/staymodernproperties/Website - https://staymodernproperties.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #AirbnbHost #EntrepreneurLife #STRBusiness #SideHustleSuccess#PropertyManagement #BusinessGrowth #WomenInBusiness #DigitalNomadLifeFollow 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 LinkedInHospitality.FMSmartStay 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! | — | ||||||
| 3/18/25 | ![]() Want to Scale Your Airbnb Portfolio? Stop Doing Everything Yourself! | Jayla Siciliano | Ever wondered if one spontaneous decision could completely change your career? That’s exactly what happened to Jayla Siciliano. While on vacation, she crunched the numbers on a short-term rental, saw its potential, and the next day, put in an offer on her first property. In this episode of SmartStay Show, Jayla takes us through her journey from that impulsive purchase to building a thriving short-term rental business across multiple states. We dive into the challenges of managing properties remotely, the importance of building a strong local team, and how she scaled her co-hosting operation while maintaining high-quality guest experiences. Jayla also shares how she overcame imposter syndrome, lessons from past entrepreneurial ventures, and why she’s now expanding into real estate development. Whether you’re a new investor or an experienced host, this episode is packed with insights and inspiration you won’t want to miss!Things we discussed in this episode: Jayla’s Unexpected Start in STRs – How a vacation rental stay led to her first property purchase. Scaling a Short-Term Rental Business – Growing from a single property to managing multiple across states. Challenges of Remote Property Management – How she successfully operates rentals from across the country. Building a Strong Local Team – The importance of having reliable "boots on the ground." Overcoming Imposter Syndrome – Transitioning from a different industry and establishing credibility in STRs. The Role of Systems and Technology – Using tools like Breezeway and OwnerRez to streamline operations. Expense & Maintenance Management – The hidden complexities of managing costs and upkeep, especially in snowy climates. Co-Hosting and Owner Relations – How she convinces owners to trust a remote management model. Real Estate Investment & Market Strategy – Why she chose Vermont and California for her properties. Future Plans & Expansion – Her podcast Seed Money and plans to develop properties on her Vermont land. . Get in touch with Jayla: Facebook - https://www.facebook.com/jayla.siciliano.akersInstagram - https://www.instagram.com/atlasvacations/Website - https://www.atlas-vacations.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #VacationRentals #AirbnbHost #Entrepreneurship #PassiveIncome #RemotePropertyManagement #CoHosting #STRBusiness #FinancialFreedomFollow 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 LinkedInHospitality.FMSmartStay 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! | — | ||||||
| 3/11/25 | ![]() Turn Your Airbnb into a Money-Making Machine with These Upgrades | Mark Lumpkin | What makes a short-term rental truly unforgettable? In this episode of SmartStayShow, we uncover the secrets behind top-performing vacation rentals with Mark Lumpkin, sales director at STRCRIBS. From bachelorette-themed escapes in Nashville to hidden speakeasies and glow-in-the-dark mini-golf, Mark shares expert tips on designing spaces that attract guests—and boost revenue. We dive into bold colors, eye-catching murals, and Instagrammable moments that make listings pop. Whether you're a new host or a seasoned investor, this episode is packed with game-changing insights to help you stand out.Things we discussed in this episode: Evolving Guest Expectations – How short-term rental guests expect more than they did 10 years ago, making amenities and design essential for success. Defining Your Guest Avatar – Understanding your ideal guest (families, couples, bachelor/bachelorette groups) and tailoring the rental experience accordingly. Themed Rentals & Market-Specific Design – Examples like bachelorette-themed homes in Nashville, Disney-themed rentals in Orlando, and ski-lodge aesthetics in Colorado. High-Impact Amenities – Features that increase bookings, such as hot tubs, barrel saunas, coffee bars, and even pickleball courts. Balancing Niche vs. Broad Appeal – The risk of hyper-themed rentals (like college football houses) and finding the right level of specialization. Bold Design & Color Psychology – How vibrant colors, murals, and statement pieces help listings stand out in crowded markets. Photography & Staging Strategies – Using professional photos, lifestyle images, and seasonal shots to capture attention and increase bookings. Budget-Friendly Upgrades – Small investments like blackout curtains, high-quality bedding, and unique wall art that enhance guest experience. Financing for Rental Upgrades – STR Cribs' 0% financing option to help hosts afford high-impact improvements without upfront costs. Innovative & Unique Amenities – Creative installations like speakeasies, indoor mini-golf, and hidden game rooms to create unforgettable stays. . Get in touch with Mark: Linkedin - https://www.linkedin.com/in/mark-lumpkin-84b173142Facebook - https://www.facebook.com/strcribsInstagram - https://www.instagram.com/strcribs_/Website - https://strcribs.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbHosting #STRCribs #VacationRentals #RentalProperty #AirbnbDesign #PassiveIncome #PropertyManagement #TravelExperienceFollow 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 LinkedInHospitality.FMSmartStay 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! | — | ||||||
| 3/4/25 | ![]() They’ve Stayed in 33 Airbnbs – Here’s What Hosts Get RIGHT! | Marissa + Eric Dingler | Ever wondered what it’s like to live as a digital nomad, staying in over 30 short-term rentals around the world? In this exciting episode of the Smart Stay Show, we sit down with Eric and Marissa Dingler, a family that sold most of their possessions and turned their home into a life of adventure. From Costa Rica to Liverpool, the Dinglers share their incredible journey and insights into the world of short-term rentals.As experienced guests, they dive into what makes a great host, the importance of functional spaces, and how to create an unforgettable guest experience. They also explore the impact of short-term rentals on local communities and how hosts can attract the growing digital nomad market.Plus, Eric offers free consultations for property owners looking to improve their listings!Don’t miss this captivating conversation packed with valuable tips and real-world insights!Things we discussed in this episode: Eric and Marissa Dingler's transition to a nomadic lifestyle, selling 95% of their possessions. The Dinglers' preferences for short-term rentals, including the need for 5 bedrooms, multiple bathrooms, and a washer/dryer. The importance of functional spaces, especially in the kitchen and bathroom, from the guest perspective. The significance of clear communication and responsiveness between hosts and long-term guests. The Dinglers' philosophy on providing honest, fair ratings based on the host-guest relationship. The impact of providing multiple keys for long-term guests and the host's responsiveness to requests. The nuanced view on the effect of short-term rentals on local housing markets and communities. The Dinglers' approach to integrating into local communities and being good neighbors as digital nomads. Eric's digital marketing agency and the offer of free consultations for property owners. The Dinglers' future plans to potentially become short-term rental hosts themselves. . Get in touch with Eric and Marissa: Linkedin - https://www.linkedin.com/in/ericdingler/Facebook - https://www.facebook.com/coastalcitycreativeInstagram - https://www.instagram.com/intransitstudios/Website - https://intransitstudios.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #Airbnb #AirbnbGuests #GuestExperience #HostCommunication #LocalCommunities #HousingImpact #FunctionalSpaces #RatingSystem #EntrepreneurialSpirit #DigitalNomadsFollow 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 LinkedInHospitality.FMSmartStay 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! | — | ||||||
| 2/25/25 | ![]() His HELOC Strategy Made STR Investing Easy (Smart Money Move!) | Jim McGowan | Can You Build a Thriving Short-Term Rental Business While Working Full-Time? In this episode, we sit down with Jim McGowan, a seasoned sales professional who has successfully built a profitable short-term rental portfolio—all while maintaining his full-time job!Jim takes us through his journey, from an early misstep in fractional ownership to fully owning and managing two stunning vacation rentals in Bartlett, New Hampshire: Summit Vista, a condo with breathtaking views, and Lift House, a sought-after ski-in/ski-out property.How did Jim make it happen? He breaks down his financing strategy, including how he leveraged a home equity line of credit (HELOC) to secure a prime property with a quick cash offer. He also shares the advantages and flexibility of this approach for aspiring investors.Tune in now to learn how you can start or grow your own short-term rental business without quitting your day job!Things we discussed in this episode: Jim's experience with fractional ownership and the limitations it presented. The decision to transition to full property ownership and the benefits it provided. The purchase of Summit Vista and the importance of the property's unique selling point (best view in New Hampshire). The acquisition of Lift House, a ski-in/ski-out property, and the use of a HELOC to finance it. The advantages of a HELOC, including the ability to make cash offers, flexible rates, and the opportunity to pay down the principal. The importance of providing excellent customer service and being responsive to guests. The strategy of focusing on what makes a property stand out in a competitive market. The impact of the COVID-19 pandemic on Jim's primary sales job and the role of the short-term rental income. The benefits of sharing the properties with friends and family, while still maintaining profitability. Jim's advice for new and aspiring short-term rental hosts, emphasizing the need to do the right thing and create a memorable experience for guests. . Get in touch with Jim: Facebook - https://www.facebook.com/summitvistanhInstagram - https://www.instagram.com/summitvistanh/Airbnb - https://www.airbnb.com/rooms/893469325980802315 https://www.airbnb.com/rooms/1039058125690946596#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #Airbnb #Vrbo #HardMoneyLending #BurrMethod #DebtServiceCoverageRatio #AirDNAData #EquityTapping #MarketDifferentiation #GuestExperience #ShortTermRentalManagement #RentalIncomeOptimizationFollow 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 LinkedInHospitality.FMSmartStay 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! | — | ||||||
| 2/18/25 | ![]() Airbnb Hosts: This Simple AI Tool Saves You HOURS Every Week! | Jay Ullrich | Can AI Handle Guest Communication Better Than You? In this episode of The Smart Stay Show, we sit down with Jay Ulrich, CEO and co-founder of HostBuddy.ai, to explore how AI is revolutionizing short-term rental management.Jay, a former civil engineer turned short-term rental host, shares his journey from scaling Select Stays to 40 units to developing an AI-powered platform that learns your style, responds like you (yes, even with emojis! 😎), and frees up your time.Hosts with 1-10 listings get affordable, 24/7 automated guest communication, while larger operators save thousands by replacing virtual assistants. But how does Host Buddy handle tricky guest questions? What’s the future of AI in STRs?Join Me and Rory as we dive into the impact of AI on hosting and the future of guest communication..Things we discussed in this episode: Introduction to Host Buddy and its potential to transform host operations Jay Ulrich's background as a short-term rental host and the development of Host Buddy The need for automated guest communications that led to the creation of Host Buddy Host Buddy's evolution from an external chatbot to a full-blown software platform Benefits of Host Buddy for smaller hosts with 1-10 properties and larger hosts with 50-70 units How Host Buddy frees up virtual assistants to focus on revenue-generating activities The importance of AI learning from past conversations to sound like the host Challenges of handling situational questions and decision-making with AI Host Buddy's ability to detect guest sentiment and generate action items The predicted widespread adoption of AI-powered guest communication in the short-term rental industry Get in touch with Jay: Instagram - https://www.instagram.com/hostbuddy_ai/#Website - https://www.hostbuddy.ai/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #ArtificialIntelligence #GuestCommunication #AutomationInSTR #HostBuddy #STROperations #VirtualAssistants #GuestExperience #IndustryTrends #FutureOfSTRFollow 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 LinkedInHospitality.FMSmartStay 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! | — | ||||||
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