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

By: Airbnb Superhost Jason Muth + Rory Gill
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  • Summary

  • Welcome to the SmartStay Show, your go-to podcast for mastering Short-Term Rentals on Airbnb, Vrbo, and beyond. For more Airbnb tips, visit smartstayshow.com and smartstaycoaching.com. Hosted by 30-time Airbnb Superhost Jason Muth and Real Estate Attorney Rory Gill, we equip you with the tools to launch, manage, and optimize your vacation rental like a pro. Unlike other shows, we specifically cater to owners of small-but-mighty portfolios who self-manage their properties. Each episode delivers expert insights, legal tips, and proven strategies from successful hosts across the U.S. Whether you’re buying your first property, improving your listing, or looking to stay ahead of the competition, we offer actionable advice and real-life stories to help you thrive. From pricing strategies to guest communication, we provide the playbook to turn your property into a top-performing rental. Subscribe now and unlock your rental’s full potential with the SmartStay Show!
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Episodes
  • The Tax Strategy Airbnb Hosts Can’t Afford to Ignore | Sean Graham

    The Tax Strategy Airbnb Hosts Can’t Afford to Ignore | Sean Graham
    May 6 2025
    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!
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    41 mins
  • Avoid the Biggest Mistakes in Airbnb Investing | John Bianchi

    Avoid the Biggest Mistakes in Airbnb Investing | John Bianchi
    Apr 29 2025
    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!
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    49 mins
  • Confident Hosts Do This Differently - Boostly's Founder Mark Simpson Explains

    Confident Hosts Do This Differently - Boostly's Founder Mark Simpson Explains
    Apr 22 2025
    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 #TechForHosts Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    43 mins

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