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Most AI agent demos start with the model. We ended up spending far more time thinking about what gets put around the model. I run 23 holiday lets and have been building AI agents into the day-to-day operation. Guest messaging sounds like one of the easier problems: Guest sends a message. Give the message to an LLM. Send back the answer. That works brilliantly right up until the guest asks: Can I park a second car?
I run short lets. Twenty three of them. About eighteen months ago I started replacing the parts of that job that were eating my evenings, mostly answering the same question about parking for the fortieth time, with AI agents. They work. They also taught me that almost everything I first believed about shipping autonomous agents was wrong. This is not a post about prompt engineering.
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