SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips

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!

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 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 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!

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 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!

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!

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!

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!

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!

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!

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!