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 -
/ jarrett.chouinard - Instagram -
/ jarrettchouinard - Website - https://www.stellaretreats.com/
➢ Subscribe: 
/ @smartstayshow
- 00:00:00 Jared's Journey Transition into short-term rentals.
- 00:03:30 Navigating Arbitrage Challenges of the model.
- 00:07:45 Adapting to Guests Differences in demographics.
- 00:11:15 Selective Clients Importance of saying no.
- 00:15:00 Leveraging Tech Systems used to manage.
- 00:20:00 Building a Team Value of a reliable team.
- 00:24:15 Expansion & New Ventures Growth plans and ideas.
- 00:28:00 Lessons Learned Insights Jared wishes he had.
- 00:31:00 Trial & Error Learning from mistakes.
- 00:34:00 Building Community Hosting a local meetup.
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