How to Handle Airbnb Guests + Issues Without Being On-Site | Jarrett Chouinard

In this episode, I’m joined by Jarrett Chouinard, the founder of Stellar Retreats, who shares his inspiring journey into the short-term rental world. Starting with just one arbitrage unit in Connecticut, Jarrett has grown his business into a thriving operation spanning multiple properties in New York, Rhode Island, and beyond. We’ll dive into his experiences with the challenges of the arbitrage model, how he navigates working with landlords, and the lessons he’s learned about guest demographics and client relationships. Jarrett also shares his approach to technology, systems, and building a team that supports growth. And as if that’s not enough, we’ll also talk about Jarrett's ambitious plans for the future and his entrepreneurial ideas that go beyond short-term rentals. This is a must-listen for anyone looking to learn, grow, and succeed in the short-term rental industry. Let’s get started!  Things we discussed in this episode: Jarrett's transition from media and advertising into short-term rentals and real estate. The challenges and risks of the Airbnb arbitrage model, including dealing with landlords. The differences in guest demographics and communication styles across Jarrett's properties in different locations. Jarrett's approach to saying no to potential clients who don't fit his standards and the importance of working with the right partners. The technology and systems Jarrett uses, including smart locks, cameras, property management software, and supply delivery. Jarrett's plans to expand Stellar Retreats to 15 clients by the end of the year and his interest in other entrepreneurial ventures. The value of building a reliable ground team and the challenges of managing properties remotely. The benefits of hosting a short-term rental meetup in New York City to build a local network and community. The lessons Jarrett wishes he had known when starting, including the importance of not being intimidated by challenges. The role of trial and error, making mistakes, and learning in growing a successful short-term rental business. Get in touch with Jarrett: Facebook - https://www.facebook.com/jarrett.chouinard Instagram - https://www.instagram.com/jarrettchouinard/ Website - https://www.stellaretreats.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #AirbnbArbitrage #PropertyManagement #EntrepreneurialMindset #HospitalityTechnology #RemoteTeamBuilding #CommunityBuilding #GuestExperience #ScalingSTRBusiness #HospitalityInsights 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!