Sam Dundas learned the hard way that running vacation rentals means answering texts at 2 a.m. about broken air conditioners and fielding requests for early check-ins while you're trying to finish dinner. After years as an Airbnb superhost—and later as Senior Director of Partnerships at hospitality startup Planned—he'd seen enough midnight emergencies to wonder if there wasn't a better way.
His answer, it turns out, was building an AI that never needs sleep.
Dundas's company, Besty AI, disclosed this week that it closed a $3.75 million seed round led by Armory Square Ventures. The New York–based startup, which automates the unglamorous work of managing short-term rentals, says it now powers operations for more than 30,000 properties spread across 25 countries. Revenue, the company claims, has quadrupled year-over-year, though it declined to share hard numbers.
Ridge Ventures, Bungalow Capital, and Grand Ventures all participated. The funding—pieced together from a $1.5 million initial close in August 2024 and a final tranche recorded in March of this year—will bankroll the usual startup ambitions: more product features, bigger sales teams, sharper marketing.
The Middleware Play
What Armory Square saw in Besty was less about replacing the clunky property management systems that dominate short-term rentals and more about sitting on top of them. The firm laid out its thinking in a May investment thesis: Besty functions as an AI orchestration layer, plugging into platforms like Guesty, Hostaway, OwnerRez, Track, and Avantio without asking operators to rip out and replace their existing infrastructure.
That matters in an industry notoriously resistant to change. Property managers tend to be small operators, often running dozens or a few hundred units, and switching platforms is the kind of headache they'd rather avoid. Besty's pitch is simpler: keep what you have, let us handle the repetitive stuff.
Ridge Ventures participated in the initial August 2024 close and came back for this round. Grand Ventures climbed aboard in 2025, a detail that surfaced in the firm's year-end review last December. Ravi Belani, who runs the Alchemist Accelerator, participated in the initial $1.5 million seed round announced in August 2024.
What It Actually Does
Besty, founded in 2023 by Dundas and Aarlo Stone Fish—a Yale-educated computer scientist—bills itself as an "AI property manager," which is perhaps both accurate and underselling it. The platform handles guest messaging across SMS, email, WhatsApp, and the various OTA platforms where listings live. But the more interesting piece is what the company calls "agentic upselling."
Here's how it works: the AI spots a gap night between bookings and autonomously nudges the guest to extend their stay, or it offers add-ons like late checkout or early check-in. When the guest bites, Besty charges the card and updates the property management system—no human required. The company says its earliest customers generated around $35,000 in upsell revenue in the first month. By mid-2025, the company reports that figure had crossed $500,000.
Other features include smart lock integration, housekeeping workflows, a unified inbox, and a direct booking widget. The roadmap hints at voice AI and more detailed owner reporting down the line.
Growing Fast, If Not Quietly
Besty reported serving more than 300 customers as of this month, up from roughly 200 when it announced the first seed close in August 2024. The team expanded from 8 to 22 employees over the past year. The company recently moved into a 6,400-square-foot headquarters in SoHo—a signal, perhaps, that the scrappy startup phase is ending—and opened an office in Toronto while expanding its European team.
Named customers include Host & Stay, BeachBox Vacation Rentals, and KRAIN Luxury Real Estate in Costa Rica. That last one, the company reported in a June LinkedIn update, has generated $70,000 in upsell revenue since October.
CB Insights pegged Besty's revenue at $1 million in 2025, though that figure is now outdated given the company's claimed 4x growth trajectory and should probably be taken with a grain of salt given how quickly these numbers can shift.
A Crowded Lane
Besty isn't alone in trying to automate the short-term rental business. Incumbents like Guesty, Hostaway, and Hospitable have all rolled out AI-powered guest communication tools in recent months. Competitors like Dimora AI and HostAI are chasing similar integrations across multiple property management ecosystems.
The company's bet is that property managers will prefer specialized AI tools that work with their existing systems rather than trusting the PMS vendors to build best-in-class AI themselves. Whether that bet pays off depends on execution—and whether the underlying platforms decide to squeeze out third-party layers altogether.
Still, the timing could be worse. Investor sentiment around short-term rentals has thawed after a rough patch. AirDNA's outlook for this year, published late last year, described conditions as the most favorable for STR investment since 2021. Stabilizing supply-demand dynamics and event-driven demand spikes—like the World Cup host cities where Airbnb bookings reportedly surged as much as 118% year-over-year in May—have made the market look attractive again.
Besty plans to plow the new capital into product development and customer acquisition, focusing on North America and Europe. Whether the AI can truly replace the human touch that hospitality has always demanded remains an open question. But for property managers fielding 2 a.m. texts about broken AC units, the appeal is obvious enough.
