• 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
    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
    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
  • I Wish I Knew These Airbnb Tax Hacks Before We Bought | Anne Gannon
    Apr 15 2025
    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=100095441858241 Instagram - https://www.youtube.com/@AcceleratorMethod Linkedin - https://www.linkedin.com/in/anne-gannon-529107148/ Website - https://www.thelargogroup.com/About https://www.accelerator-method.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #TaxStrategy #PassiveIncome #TaxPlanning #RealEstateWealth #InvestmentTips #PropertyInvestment #FinancialFreedom #STRTaxBenefits Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    40 mins
  • Luxury STR Hosts Are Using This Exclusive Booking Model! | Kevin Duran
    Apr 8 2025
    "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/JKWVacation Website - https://jkwvacationclub.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #LuxuryTravel #VacationClub #TravelExperiences #PropertyInvestment #HospitalityInnovation #AIinTravel #ConciergeService #TravelTech #STRBusiness Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!
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    30 mins
  • Why Making Your Airbnb ACCESSIBLE is a Smart Business Move! | Mrs. Schneider
    Apr 1 2025
    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=61567628681216 Instagram - 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 #TravelInclusion 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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    40 mins
  • Betting on Yourself + Leaving a Lucrative Career for STRs (WAS IT WORTH IT?) | Payton Cummings
    Mar 25 2025
    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.7 Instagram - https://www.instagram.com/staymodernproperties/ Website - https://staymodernproperties.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #AirbnbHost #EntrepreneurLife #STRBusiness #SideHustleSuccess #PropertyManagement #BusinessGrowth #WomenInBusiness #DigitalNomadLife 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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    35 mins
  • Want to Scale Your Airbnb Portfolio? Stop Doing Everything Yourself! | Jayla Siciliano
    Mar 18 2025
    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.akers Instagram - https://www.instagram.com/atlasvacations/ Website - https://www.atlas-vacations.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #VacationRentals #AirbnbHost #Entrepreneurship #PassiveIncome #RemotePropertyManagement #CoHosting #STRBusiness #FinancialFreedom 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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    35 mins