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!

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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

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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!

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!

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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

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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 makes a short-term rental truly unforgettable? In this episode of SmartStayShow, we uncover the secrets behind top-performing vacation rentals with Mark Lumpkin, sales director at STRCRIBS. From bachelorette-themed escapes in Nashville to hidden speakeasies and glow-in-the-dark mini-golf, Mark shares expert tips on designing spaces that attract guests—and boost revenue.

We dive into bold colors, eye-catching murals, and Instagrammable moments that make listings pop. Whether you're a new host or a seasoned investor, this episode is packed with game-changing insights to help you stand out.

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Linkedin - https://www.linkedin.com/in/mark-lumpkin-84b173142

Facebook - https://www.facebook.com/strcribs

Instagram - https://www.instagram.com/strcribs_/

Website - https://strcribs.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbHosting #STRCribs #VacationRentals #RentalProperty #AirbnbDesign #PassiveIncome #PropertyManagement #TravelExperience

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!

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!

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Linkedin - https://www.linkedin.com/in/ericdingler/

Facebook - https://www.facebook.com/coastalcitycreative

Instagram - https://www.instagram.com/intransitstudios/

Website - https://intransitstudios.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #Airbnb #AirbnbGuests #GuestExperience #HostCommunication #LocalCommunities #HousingImpact #FunctionalSpaces #RatingSystem #EntrepreneurialSpirit #DigitalNomads

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!

Can You Build a Thriving Short-Term Rental Business While Working Full-Time?

In this episode, we sit down with Jim McGowan, a seasoned sales professional who has successfully built a profitable short-term rental portfolio—all while maintaining his full-time job!

Jim takes us through his journey, from an early misstep in fractional ownership to fully owning and managing two stunning vacation rentals in Bartlett, New Hampshire: Summit Vista, a condo with breathtaking views, and Lift House, a sought-after ski-in/ski-out property.

How did Jim make it happen? He breaks down his financing strategy, including how he leveraged a home equity line of credit (HELOC) to secure a prime property with a quick cash offer. He also shares the advantages and flexibility of this approach for aspiring investors.

Tune in now to learn how you can start or grow your own short-term rental business without quitting your day job!

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Facebook - https://www.facebook.com/summitvistanh

Instagram - https://www.instagram.com/summitvistanh/

Airbnb - https://www.airbnb.com/rooms/893469325980802315

https://www.airbnb.com/rooms/1039058125690946596

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #Airbnb #Vrbo #HardMoneyLending #BurrMethod #DebtServiceCoverageRatio #AirDNAData #EquityTapping #MarketDifferentiation #GuestExperience #ShortTermRentalManagement #RentalIncomeOptimization

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!

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..

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 #FutureOfSTR

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!

Can hard money lending and short-term rentals be the ultimate power duo?

In this episode of The Smart Stay Show, We sit down with David Little, co-founder of Crown Capital Resources, to explore how savvy investors are using short-term rentals as a game-changing exit strategy.

We dig into DSCR loans, the Burr method for vacation rentals, and how tools like AirDNA are influencing lending decisions. David shares insider tips on leveraging your property’s equity and why guest experience is more critical than ever in competitive markets like Austin.

Plus, we discuss the opportunities—and challenges—of hard money lending for short-term rental hosts. Whether you're looking to refinance, scale, or simply understand the numbers, this episode is packed with actionable advice.

Email - [email protected]

Website - https://crowncapitalresources.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #HardMoneyLending #BRRRRMethod #DebtServiceCoverageRatio #AirDNAData #EquityTapping #MarketDifferentiation #GuestExperience #ShortTermRentalManagement #RentalIncomeOptimization

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!

How did one property cover an entire mortgage—and spark a 30-property empire?

In this episode of the Smart Stay Show, We sit down with Islam Elgarhi, a short-term rental investor and entrepreneur, to uncover how he turned a chance discovery into a thriving business.

From scaling his portfolio with smart systems to creating an AI tool that helps hosts tackle unfair reviews, Islam shares his secrets for success. Plus, we explore how his martial arts background has shaped his mindset for resilience and growth in the fast-paced world of Airbnb hosting.

If you’re ready to learn how innovation and discipline can transform your short-term rental game, this episode is packed with inspiration and actionable insights!

Linkedin - https://www.linkedin.com/in/islam-elgarhi/

Instagram - https://www.instagram.com/islamelgarhi/

Website - https://modernstayconsulting.com/

Website - https://www.reviewlawyer.ai/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #Airbnb #Entrepreneurship #SystemsDevelopment #VirtualAssistants #ArtificialIntelligence #ReviewManagement #MartialArts #FocusAndDiscipline #InnovationInRealEstate

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!

Ever wonder why some hosts seem to always get glowing reviews while others struggle?

In this episode of the Smart Stay Show, I’m joined by my business partners Alex Steeg and Kory Himmer to dive into the game-changing power of proactive communication in short-term rental hosting.

We break down how setting clear expectations upfront can prevent negative reviews and enhance guest satisfaction. From booking confirmations to review requests, we share a 5-step strategy to keep your guests informed and your business running smoothly. Plus, we discuss the latest tech tools to streamline communication and make your life easier.

If you’re ready to take your hosting to the next level, this episode is a must-listen!

Facebook - https://www.facebook.com/kory.himmer

Instagram - https://www.instagram.com/603bnb/

Website - https://603bnb.com/ / https://www.smartstaycoaching.com/

Facebook - https://www.facebook.com/alex.steeg86

Instagram - https://www.instagram.com/alexsteeg/

Website - https://www.shorewaymgmt.com/ / https://www.smartstaycoaching.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #GuestCommunication #ProactiveHosting #AirbnbHosting #VRBOHosting #GuestExperience #AutomatedMessages #AIResponses #HostingTips #STRSuccess

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!

Ever Dealt With a Water Damaged Rental Property? This Could Save You Thousands.

As short-term rental owners, Rory and I have seen it all - from the good, the bad, to the downright disastrous. One fateful night, we got that dreaded 2am call about a water damaged property, and let me tell you, it was a nightmare. 

But what happened next is the real story. In this episode, we sit down with Darren Pettyjohn, the co-founder of Proper Insurance, to unpack why short-term rental insurance is so crucial - and how their specialized coverage saved our bacon when disaster struck.

Darren pulls back the curtain on the unique challenges facing vacation rental owners, the sneaky tricks some insurance companies use, and the innovative solutions Proper has pioneered. If you own a short-term rental property, or are thinking about getting into the game, you won't want to miss this. 

It could be the difference between a minor headache and a total nightmare. Click play and find out how Proper Insurance can give you the peace of mind to focus on being a 5-star host.

Facebook - https://www.facebook.com/propervacationrentalinsurance

Instagram - https://www.instagram.com/properinsurance/

Website - https://www.proper.insure/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #ShortTermRentalInsurance #PropertyProtection #ClaimsManagement #VacationRentalOwners #RiskManagement #PropertyManagerInsurance #GuestDamageProtection #EntrepreneurialInsights #InsuranceInnovation #PeaceOfMind

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!

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!