The story of how Chatty Patty was born from real frustration with rental inquiries, no-shows, and sleepless nights answering "Is this still available?"
It was 2:30 AM on a Tuesday when my phone buzzed for the 47th time that day:
"Is this still available?"
I had a 2BR in Somerville listed on Facebook Marketplace. By the end of that week, I'd received over 200 texts asking the same basic questions:
I had built a successful tech business before getting into real estate. I knew there had to be a better way.
That's when the idea hit me: What if I could create an AI assistant that could handle all these repetitive conversations, screen prospects automatically, and only send me qualified candidates ready to view the property?
I spent six months building the first version of what would become Chatty Patty. The goal was simple: create an AI that could have natural conversations with prospects, ask the right screening questions, and schedule showings with qualified candidates only.
The first test was on my own property. Instead of posting my personal number, I used Patty's number and watched the magic happen:
It worked. But more importantly, other landlords in my network started asking how they could use it too.
We believe property management should enhance your life, not consume it. Every hour you spend answering "Is this still available?" is an hour stolen from your family, your business, or your peace of mind.
Our team manages over 200 rental units across Massachusetts
15+ years building conversational AI and automation systems
Every feature is tested on our own properties first
Not a generic chatbot. Patty understands rental terminology, screening questions, and property management workflows.
Trained on MA rental regulations, fair housing laws, and Section 8 requirements.
Every feature is battle-tested on real properties before release.
Pay once per listing, not monthly. We only make money when you successfully fill vacancies.
Our support team includes active property managers who understand your challenges.
Patty learns from thousands of conversations to get better at screening and scheduling.
Chatty Patty is just the beginning. Our vision is to build a complete suite of AI-powered tools that help landlords manage their properties more efficiently:
Our commitment: Every new feature will be tested on our own properties first and designed to save you time, not create more complexity.
Ready to get your nights and weekends back? Join hundreds of Massachusetts landlords who've already discovered the power of Chatty Patty.
Built by landlords, for landlords. Money-back guarantee.