Introducing Besty: The AI Super App for Short-Term Rentals
By: Tim Streit
In the ever-evolving and rapidly growing world of short-term rentals (STR), property managers are increasingly seeking innovative ways to streamline operations, enhance guest experiences, and drive profitability. Enter Besty, an AI-powered platform designed to revolutionize how property managers handle guest communications, optimize pricing, and automate day-to-day tasks. With its unique combination of AI technology and hands-on industry experience, Besty is setting a new standard for the STR market.
Besty’s platform automates essential tasks such as guest messaging, upselling opportunities, and operational workflows within Property Management Systems (PMS). Its AI system optimizes revenue through dynamic pricing adjustments, simplifies booking management, and generates powerful reports to help property managers maximize their profits while improving efficiency.
The Latest Platform Updates
Most recently, Besty announced a new suite of features aimed at better integrating with PMS providers, further enhancing its capabilities in the short-term rental space. These updates include:
- Automated Guest Messaging: Besty’s automated messaging reduces costs and response times. It offers customizable response delays and a review responder that generates personalized replies in the guest’s language, which can be auto-published or saved for approval.
- Upselling Opportunities: Besty enables dynamic gap night upselling, sentiment scoring, and instant translations. Its hybrid booking widget combines AI and human input to enhance conversions and streamline upselling, boosting revenue without extra complexity.
- Operational Automation: Besty automates tasks like review management, sentiment analysis, and conversation summaries, integrating with platforms like Guesty for a unified inbox. This frees property managers to focus on growth, not administrative tasks.
The key distinction lies in the business model: hotels operate as standardized, professionally managed businesses, while STRs are more decentralized, often involving independent owners and dynamic pricing strategies.
Why It Matters
We can all relate to inbox fatigue—the feeling that we’ll never catch up with the constant wave of incoming messages, especially in the AI era, when customers can send them more easily than ever. Years ago, I managed a short-term rental and remember exchanging dozens of messages with guests weekly, not to mention vendors and prospective customers. In the past, if you were committed to delivering excellent customer service, brute force was the only real solution.
That’s where AI comes in. Besty integrates seamlessly into PMS platforms, providing a unified inbox that automates messages to enhance and personalize the customer journey—essentially serving as “autopilot for the full customer journey.” In my opinion, this is AI’s greatest breakthrough. Rather than a one-size-fits-all approach, AI enables endless possibilities to create a tailored customer journey. We believe Besty can deliver this experience for the STR market.
Growing the Pie
In most industries, increasing revenue means taking market share away from competitors. However, in the world of short-term rentals, Besty empowers owners and property managers to expand the market. By offering new services like early check-ins, gap night bookings, and premium amenities, Besty helps property managers provide added value to guests while generating incremental revenue.
Just like Uber did for “passive fleets” of vehicles, leveraging other people’s unutilized assets to create profitable new sources of revenue is an exciting vision.
The Growing Market
The short-term rental market is both large and rapid-growing, driven by the rise of platforms like Airbnb and the shift toward remote work and flexible travel in the post-COVID world. As travelers increasingly seek immersive cultural experiences, short-term rentals provide a unique alternative to traditional hotels. However, with these enriched experiences come added complexities for property managers. Guests require clear guidance on entry and exit procedures, cleaning protocols, and various home-specific details such as internet, cable, and other amenities. While static instruction manuals offer basic support, a more dynamic, interactive approach to guest assistance can significantly enhance the overall experience.
Timing: Why Now?
We firmly believe that AI has transformed the tech landscape, especially in the past few quarters. Companies today fall into one of two categories: AI-strong startups—founded within the last 12 to 36 months—or established companies racing to integrate AI into existing platforms. While both have the potential to thrive, we are particularly focused on investing in AI-strong companies—those poised to shape the future of vertical AI within their respective industries.
A Truly AI-Native Team
I could have started with the team, but in this case, I saved the best for last. Besty was founded by Sam Dundas who conceived the idea for Besty after personally managing a portfolio of rentals. He joined forces with Aarlo Stone Fish, a true pioneer in AI with a passion for coding that started at age 12, blending technical genius with artistic talent. Together, they have crafted a platform that brings together the best of both worlds: real-world insights from property management and next-generation AI innovations.
The Besty team is a mix of engineers, AI pioneers, and real-world property managers, each bringing their unique expertise to the table. From All-State Band and Chorus members to University of Michigan, CMU, and Caltech engineers, this eclectic team is uniquely positioned to drive success in the AI space.With that, we’d like to offer an official Welcome Besty! We’re thrilled to work with you and excited for the great future you will build!
