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!
    © 2024 SmartStay Show
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Episodes
  • Cracking the Code to Profitable Midterm Rentals | Mike Stone

    Cracking the Code to Profitable Midterm Rentals | Mike Stone
    Nov 5 2024
    Have you ever wondered if the skills you’ve developed in your day job could translate into a thriving business? Meet Mike Stone—a former corporate attorney who transformed his career, channeling his expertise into building a successful short- and medium-term rental empire. Mike’s journey began with an ambitious leap from the legal world into vacation rentals, and his success speaks to the power of leveraging industry insights in new ways. In this episode, Mike opens up about his pivot from attorney to rental entrepreneur, sharing how he secures high-yield, mid-term bookings by targeting insurance companies rather than traditional vacation renters. He provides insider tips on navigating the rental space, detailing his experience with Airbnb arbitrage—a venture that proved costly but ultimately led him to a co-hosting model he’s convinced is far more sustainable and profitable. Tune in as Mike reveals essential strategies for building credibility, tapping into your network, and finding unique opportunities in the rental industry, including landing a $12,000/month contract for a 12,000-square-foot property. Whether you’re curious about the transition into real estate or looking to expand your rental business, Mike’s story offers invaluable lessons and inspiration! Things we discussed in this episode: Mike Stone's transition from corporate attorney to short-term rental entrepreneur His experience with Airbnb arbitrage, including a costly failed deal The benefits of co-hosting over arbitrage, including equity, appreciation, and tax advantages Pro tips for mitigating risk in arbitrage deals The importance of leveraging group reputation to secure initial co-hosting opportunities Mike's recent success in securing a $12,000/month contract for a 12,000 sq ft home The process of building relationships with insurance companies for medium-term rentals The negotiation dynamics when working with insurance companies vs. individual renters Strategies for targeting medium-term rentals during short-term rental slow seasons The value of asking for higher prices and not accepting lower offers from individual renters Get in touch with Mike: Website -https://www.strignite.com / https://allstr.com Linkedin - https://www.linkedin.com/in/mike-stone-5a303b31/ Facebook - https://www.facebook.com/mstone219/about #SmartStayShow #realestate #realestateinvesting #realestateinvestor #realestatelaw #realestateagent #socialmedia #realestatemarketing #ShortTermRentals #MediumTermRentals #Airbnb #RealEstateInvesting #PropertyManagement #CareerChange #PersonalDevelopment #InsuranceCompanies #Masterminds #EntrepreneurLife ***** Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for another 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 SmartStay Coaching Website and on Instagram Straightforward Short-Term Rentals Website Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn ***** This podcast and these show notes are not legal advice, but we hope you find both entertaining and informative. 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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    20 mins
  • Secrets to Managing Large Rentals (Stay Booked Method) | Andrew Rodriguez

    Secrets to Managing Large Rentals (Stay Booked Method) | Andrew Rodriguez
    Oct 31 2024
    Today, we're thrilled to welcome Andrew Rodriguez, the co-owner of Stay Booked, a full-service short-term rental management company. Andrew and his wife, Lindsay, have built an impressive portfolio of larger, unique vacation homes in sought-after destinations like the Poconos. What sets Andrew and his team apart is their unwavering commitment to quality over quantity. From the moment a guest lays eyes on one of their properties to the second they check out, Andrew and his crew strive to deliver an exceptional experience. With a background in sales and a keen eye for detail, Andrew has developed a unique approach to short-term rental management that has earned him a loyal following. He's here today to share his insights on building a successful STR business, navigating the challenges of managing larger properties, and fostering a strong sense of community within the industry. So, let's dive in and learn from Andrew's wealth of knowledge and experience. Things we discussed in this episode: Andrew Rodriguez's emphasis on "quality over quantity" in his short-term rental business The story of how Andrew and his wife Lindsay got into the short-term rental industry Their use of FHA and second home loans to acquire properties, including a 6-bedroom cabin in the Poconos The importance of professional design and attention to detail in their properties The challenges of managing larger short-term rental properties, including the need for a trusted "runner" Strategies for handling guest feedback, both positive and negative The evolving expectations of short-term rental guests and the value of empathy The role of community and networking within the short-term rental industry Andrew's belief that anyone can achieve their short-term rental dreams with dedication The meetup group Andrew and a fellow mastermind member started in New York City Get in touch with Andrew: Facebook - https://www.facebook.com/profile.php?id=61552248421123 Linkedin - https://www.instagram.com/yourstaybooked/ Website - https://www.stay-booked.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #VacationRentals #GuestExperience #PropertyManagement #EntrepreneurLife #CommunityBuilding #HospitalityIndustry #SuccessStories 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
  • The Secret to 80% Direct Bookings & Happy Guests! | Rose Tipka

    The Secret to 80% Direct Bookings & Happy Guests! | Rose Tipka
    Oct 29 2024
    In today’s episode, I’m excited to introduce you to a truly inspiring figure in the vacation rental industry, Rose Tipka. Rose isn't just a successful short-term rental host; she's a homeschooling mom of six who's managed to build a multi-million-dollar portfolio while maintaining an admirable work-life balance. Her journey into vacation rentals started unexpectedly when her husband purchased their first property just a day before she gave birth to their fifth child! Instead of seeing this as a challenge, Rose embraced the opportunity with incredible determination. With 80% of her bookings coming directly through her website and 60% of her guests being repeat customers, Rose's approach to hospitality is clearly working. In this conversation, we’ll explore how she’s built her brand, diversified her booking sources, and balanced entrepreneurship with motherhood. Whether you're a seasoned host or new to the game, Rose’s insights offer a fresh, inspiring perspective on thriving in the vacation rental world. Let’s dive in! Things we discussed in this episode: Rose Tipka's background as a homeschooling mom of six and how that has shaped her entrepreneurial drive. The unexpected start of her vacation rental business when her husband purchased their first property without her initial knowledge. The importance of maintaining a work-life balance and being present for her family while growing a successful business. Rose's strategic decision to focus on high-end vacation rentals with average daily rates between $600-$1000. The power of branding and how Rose has built a cohesive brand experience across her properties, marketing, and customer interactions. Rose's use of "magic phrases" to reinforce her brand values, such as friendliness and hospitality. The personalized customer service tactics Rose employs, including video greetings, handwritten thank-you notes, and branded fridge magnets. The significance of diversifying booking sources beyond third-party platforms like Airbnb and Vrbo to build a sustainable business. The challenges of unpredictability and account suspensions on OTA platforms, and the importance of having a standalone business. The lessons Rose has learned in balancing entrepreneurship and parenthood, and the "ferocity" that comes with being a mom in business. Get in touch with Rose: Website - https://yourfamilysplace.com/ Email - rose@yourfamilysplace.com Facebook - https://www.facebook.com/yourfamilysplace YouTube - https://www.youtube.com/channel/UCP79fgBZ2vzH2dGUuLavY6A Instagram - https://www.instagram.com/yourfamilysplace_/ #SmartStayShow #realestate #realestateinvesting #realestateinvestor #realestatelaw #realestateagent #RealEstateNegotiation #ShortTermRentals #VacationRentalMarketing #VacationRentalBranding #VacationRentalHospitality #VacationRentalManagement #VacationRentalSEO #VacationRentalInfluencers #WorkLifeBalanceEntrepreneur #RemotePropertyManagement #VacationRentalCustomerService #WomenInBusiness ***** Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for another episode of SmartStay Show! ***** SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn SmartStay Coaching Website and on Instagram Straightforward Short-Term Rentals Website Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn ***** This podcast and these show notes are not legal advice, but we hope you find both entertaining and informative. 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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    27 mins

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