On this week’s episode of Short Term Rental Management, Luke Carl sits down with Sam and Jay, the founders of HostBuddy AI, to break down how their property management journey led them to build an AI tool that automates guest communication. They share how scaling to 30–40 units exposed the nonstop demands of messaging, late-night guest issues, and operational burnout—ultimately pushing them to create a solution that handles 85–90% of guest communication automatically. The conversation dives into how AI can replace VAs, improve response times and reviews, personalize guest messaging, and help operators scale without sacrificing their time or sanity, while still emphasizing the importance of strong SOPs and human oversight.

How to connect with Jay and Sam

https://www.hostbuddy.ai/

@sam_mayes

@jay_ullrich_

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

Short Term Shop Plus - stsplus.com

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For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon