The Short Term Show How HelloHost AI Levels Up Your Hosting with Annie Li
Sep 24, 2025
In this conversation, Annie Lee, co-founder of Hello Host and a seasoned short-term rental operator, explains how their AI platform automates guest communications seamlessly. She shares insights on how the AI learns from past interactions, makes judgment calls on guest issues, and emphasizes the importance of maintaining a human touch in hosting. Annie also discusses the future of AI in the industry, practical tips for evaluating AI vendors, and her journey in the tech startup world, providing valuable advice for hosts looking to enhance their guest experience.
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Founder Story That Sparked Hello Host
- Annie Lee started hosting in 2014 and bought a lakeside multi-unit retreat in 2022 which exposed operational gaps.
- Losing her GM forced her into guest comms and inspired building Hello Host to automate that burden.
Autopilot Messaging, Not Drafts
- Hello Host connects to a PMS and fully automates guest messaging on autopilot without drafts.
- The company accepts responsibility for outgoing messages and prioritizes high quality and accuracy.
Train AI With History And Permissions
- Use past conversation history and listing data to train the AI and set explicit permissions for actions.
- Give feedback to refine responses and define whether AI can promise services or must escalate.
