『SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips』のカバーアート

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

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

著者： Airbnb Superhost Jason Muth + Rory Gill
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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!

Airbnb Superhost Jason Muth + Rory Gill 個人ファイナンス 経済学
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  • My Airbnb Ops Were Complete Chaos... Until I Did THIS | Michael Dinwiddie

    My Airbnb Ops Were Complete Chaos... Until I Did THIS | Michael Dinwiddie
    2025/09/09
    What if one tool could organize your entire short-term rental business—and actually give you your time back? In this episode, we sit down with hospitality veteran turned systems expert Michael Dinwiddie to talk about the real-world challenges of managing short-term rentals and how the right systems can transform your operation from chaos to calm. Michael shares how he uses Notion as a “second brain” to streamline everything from SOPs to onboarding, and why even single-property hosts can benefit from getting organized early. The conversation dives into practical strategies for empowering virtual assistants, leveraging AI, and building a business that runs smoothly—even when you’re not around. Whether you’re just starting out or scaling up, this episode is packed with insights and inspiration to help you get out of the weeds and take control of your business.Things we discussed in this episode:The importance of systematizing short-term rental operations to reduce chaos and anxiety.Using Notion as a “second brain” to organize property information, SOPs, and tasks.The benefits of documenting processes for scalability and team empowerment.Leveraging Notion’s AI features to summarize SOPs and answer operational questions.Onboarding and training new team members, including local operations managers and virtual assistants.The transition from handling everything personally to delegating guest communications and tasks.Building recurring task systems for proactive property maintenance.The value of empowering and trusting your team to deliver excellent service.Personal stories about business growth, work-life balance, and learning from experience.Michael Dinwiddie’s journey in hospitality, business expansion, and creating training resources for others.Get in touch with Michael:Instagram - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/cometogethere/⁠Facebook - ⁠https://www.facebook.com/togetherevacationrentals⁠Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://togetherevacationrentals.com/⁠#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals AirbnbHost #PropertyManagement #Notion #BusinessSystems #VacationRental #Automation #TeamBuilding #HospitalityIndustry #ProductivityHacksFollow 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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
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    37 分
  • Why I Stopped Trusting Airbnb Alone for Last-Minute Bookings (and did THIS) | Alex Alioto

    Why I Stopped Trusting Airbnb Alone for Last-Minute Bookings (and did THIS) | Alex Alioto
    2025/09/02
    Can Last-Minute Bookings Actually Boost Your STR Revenue? Last-minute bookings aren’t just a backup plan anymore—they’re becoming a key revenue strategy for short-term rental hosts. In this episode, we sit down with Alex Alioto, co-founder of Whimstay, about how shifting traveler behavior—especially among Gen Z and millennials—is reshaping the way hosts think about occupancy, pricing, and calendar gaps.Alex shares how Whimstay helps property owners capture value from expiring inventory, extend the shoulder season, and stay ahead of modern travel trends. The conversation dives into how hosts can adapt their strategies to meet rising demand for flexibility, while still delivering standout guest experiences.Whether you’re a seasoned host or just exploring the STR space, this episode offers fresh insight into the future of vacation rental booking behavior—and how to make it work in your favor.Things we discussed in this episode:The strategy and benefits of filling last-minute gaps in vacation rental calendars.How Gen Z and millennial travelers are driving the trend toward shorter booking windows.The founding story and unique value proposition of Whimstay as a last-minute rental marketplace.The importance of a diverse distribution strategy for property owners.Differences in traveler behavior and expectations across generations.The impact of remote work on travel patterns and booking flexibility.Operational challenges, such as integration with property management systems and avoiding double bookings.Pricing strategies, including last-minute discounts and dynamic pricing tools.The potential to extend the shoulder season and increase off-season bookings.The role of guest experience and local touches in attracting modern travelers.Get in touch with Alex:Instagram - ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/whimstay/LinkedIn - ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/18786646/admin/dashboard/Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.whimstay.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #VacationRentals #LastMinuteBookings #TravelTrends #Whimstay #GenZTravel #MillennialTravel #PropertyManagement #DynamicPricing #GuestExperienceFollow 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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
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    32 分
  • Quitting My Job for Short-Term Rentals (Everything I Learned) | Jake Martin

    Quitting My Job for Short-Term Rentals (Everything I Learned) | Jake Martin
    2025/08/26
    What does it really take to break free from the 9-to-5 and build a thriving short-term rental business?In this episode, We sit down with Jake Martin, a former corporate professional who left the security of his W2 job to chase a different kind of success—one built on freedom, flexibility, and financial independence.Jake opens up about the real story behind his transition: the fears, the failures, and the big wins. From learning the ropes of vacation rental investing in San Diego to managing multiple properties and navigating tough decisions, Jake shares hard-earned lessons and no-fluff advice for anyone dreaming of a similar leap.Whether you're exploring co-hosting, thinking about your first property, or simply craving a raw and honest take on entrepreneurship, this episode delivers both inspiration and actionable insights.🎧 Tune in and get ready to rethink what’s possible.Things we discussed in this episode:Jake Martin’s decision to leave his corporate job and pursue real estate investing.The impact of corporate layoffs and lack of loyalty on career choices.Early investments in syndication deals and short-term rentals.The process and challenges of renovating and managing properties during COVID.Transitioning personal residences into income-generating short-term rentals.The financial strategy of covering mortgages through rental income.Building and growing a co-hosting business (Lodge and Leisure) in San Diego.Methods for finding and acquiring new property management clients.Common issues faced by property owners, such as maintenance, design, and guest experience.Advice for aspiring entrepreneurs and real estate investors, emphasizing adaptability and problem-solving.Get in touch with Jake:Email - ⁠⁠⁠⁠⁠⁠info@lodgeandleisure.comLinkedIn - ⁠⁠⁠⁠⁠https://www.linkedin.com/in/jacob-r-martinWebsite - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.lodgeandleisure.com/#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Entrepreneurship #VacationRentals #PropertyManagement #CoHosting #FinancialFreedom #BusinessGrowth #AirbnbHost #InvestSmartFollow 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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
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    36 分
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