We’re pleased to announce that we led the Series Seed-2 round in Besty AI, an AI-native operating system reimagining how short-term rental (STR) and extended-stay property managers run their businesses.

On paper, managing an STR portfolio sounds simple: take the booking, message the guest, hand off the keys, clean the unit, repeat. In practice, every step splinters across a different vendor. The property management system (PMS) tracks reservations. A separate inbox handles guest communication, while another platform runs upsells. Smart locks live in their own portal. Cleaners are coordinated through ops software, or informally over text and WhatsApp. Owner reporting might happen in a fifth system. Somewhere in the middle, a staff member is fighting fires at 11pm on a Saturday when a guest can’t get into the unit.

The legacy PMS players that own the system of record have responded by bolting AI features onto pre-LLM architectures, but their roadmaps have to serve every other module too. Meanwhile, a newer wave of AI-native PMS challengers proposes the opposite: rip out the system of record entirely and re-platform onto a modern stack. For any operator with real revenue at stake, that migration is a non-starter.

The result is an industry where automation has been promised for years, but real autonomy (e.g. guest questions auto-resolved, gap nights proactively sold, exceptions routed to the right person) has remained out of reach.

Besty is built to change that, owing in large part to the highly differentiated skillsets of its two cofounders.

Sam Dundas lived the pain firsthand as an Airbnb super host who managed dozens of properties before joining Planned, a Series B hospitality startup, as Senior Director of Partnerships, where he led strategic integrations across the industry. He brings the operator’s instinct for what actually breaks at scale, paired with the go-to-market rigor to build a repeatable sales motion around it.

Aarlo Stone Fish is a Yale-educated serial entrepreneur and full-stack engineer with nearly two decades of experience scaling software ventures. He has been twice mentored through Alchemist Accelerator and is regarded as one of the strongest technologists to come through the program. His high bar for engineering talent is a meaningful reason Besty has shipped so much with so small a team.

Why We Invested

Besty’s wedge is structural. Rather than competing for the system of record, the platform integrates on top of the PMS landscape (think platforms like Guesty, Hostaway, Streamline, TravelNet Solutions (TRACK), Hostfully, and a growing roster of others) and acts as the AI brain that orchestrates everything operators actually do day-to-day. This includes guest communication across SMS, email, WhatsApp, and OTAs; automated upsells for early check-ins, late checkouts, and gap nights; smart-lock and IoT management; not to mention an ever-expanding roadmap reaching into housekeeping, maintenance, voice AI, and owner reporting.

This “Switzerland” posture is a strategic must given the fragmented nature of the PMS market, where no platform holds a dominant share and steep migration costs keep operators locked into whichever system they’re already on. What has historically been the industry’s biggest problem is precisely what makes Besty’s distribution model work: each PMS marketplace is its own captive demand pool, and every integration becomes both a technical pipe and an inbound channel. Today, integration partners already drive a meaningful share of new business.

Underneath the integration layer, an AI flywheel compounds. Every guest interaction, upsell outcome, and property-specific quirk feeds the platform’s knowledge base. Models get better at resolving multi-part inquiries, pricing gap nights, and routing exceptions to the appropriate person. The longer a customer runs on Besty, the harder it is to leave, not because of any contractual lock-in, but because the system has learned their properties so well that it becomes a truly invaluable assistant.

What we heard from customers consistently was that Besty becomes mission-critical infrastructure within weeks of going live: handling the majority of inbound guest messages, generating real incremental revenue through its upselling engine, and consolidating several point solutions into a single platform. This is exactly the sort of stickiness we look for in vertical AI solutions competing in crowded markets.

The short-term rental market is enormous, growing faster than GDP, and structurally underserved by software that was built before LLMs were viable. Sam and Aarlo are a true power duo, bringing the rare combination of an operator who has lived the problem and a technologist who can build the solution, while executing with the kind of speed that lets a small company define a category before the incumbents catch up. We are thrilled to be partnering with our co-investors at Grand Ventures, Ridge Ventures, and Bungalow Capital in backing this dynamic team.