He Left Tech Sales to Run Airbnbs (and Undercoat Cars?) Morgan Steir

Ever wondered what it takes to leave a tech career and build a thriving short-term rental business? In this episode, Morgan Steir joins me to share his journey from tech sales to managing a successful lakeside cabin in New Hampshire. Hear his honest insights on self-managing rentals, launching a home services franchise, and mastering everything from guest experience to vendor challenges. A must-listen for anyone looking to grow as a host and entrepreneur. Things we discussed in this episode: Morgan Steir’s transition from tech sales to launching a short-term rental business. The importance and challenges of self-managing a rental property. Guest experience, feedback, and adapting operations to improve reviews. The financial benefits and realities of owning a vacation rental. Launching “Undercover Undercoatings,” a vehicle services franchise. Dealing with platform policy changes and power dynamics (e.g., Airbnb). Managing and maintaining amenities like hot tubs and handling related guest claims. Handling property damage, insurance policies, and navigating claims. Building strong vendor relationships and paying for quality service. The value of coaching from Smart Stay to fast-track rental success and avoid common pitfalls. Get in touch with Morgan: Instagram - ⁠ Facebook - ⁠ Website - ⁠

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He Left Tech Sales to Run Airbnbs (and Undercoat Cars?) Morgan Steir is an episode from The Real Estate Law Podcast by Airbnb Superhost Jason Muth + Rory Gill.

This episode is 00:42:26 long.

This episode was published on Oct 28, 2025.

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