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Real estate is one of the largest and more operationally complex sectors of the economy. And yet, for all its scale and sophistication, it has lagged behind other industries in adopting AI, particularly in the parts of the business that matter most. While operators have modernized back-office systems like rent collection and maintenance, the core revenue driver – leasing and renewals – remains largely manual or handled by first-gen AI chatbots. These processes are often supported today by CRUD software that manages data and “keep the trains running” but lack the modern AI-enabled tools to enable operators to truly thrive.
That gap is costly. Vacancy loss alone erases more than $500B in asset value, draining value from even the best-managed portfolios, and the competition among operators for tenants can be fierce in even the smallest regional markets.
We believe Grotto brings applied AI to the front lines of leasing. Using conversational intelligence and predictive modeling, Grotto helps teams uplevel how they engage with prospects and residents, enabling a shift from reactive, ad hoc decision-making to proactive, data-driven planning. The result isn’t automation for its own sake; it’s better human decisions, powered with smarter data.
This approach is rooted in a simple but powerful insight. When Grotto analyzed millions of leasing conversations, the data showed that the highest-converting interactions aren't the ones that can be scripted or automated. They're the ones where a human builds genuine rapport. Grotto is built around this understanding: that the path to top-line growth runs through empowering leasing teams, not replacing them.
Today, we’re proud to announce our partnership with Grotto by leading their Seed round, and to support founders Nick Deveau and Ben Epstein, two builders whose clarity, technical depth, and conviction have already set a high bar for what an early-stage team can achieve.
In our view, Grotto’s focus is clear: solving one of the most fundamental and overlooked challenges in real estate. By helping operators better manage and anticipate vacancy, the company is helping turn an age-old operational problem into a new source of measurable performance improvement. At the heart of this effort is Guidance, Grotto’s leasing copilot, built to equip real estate professionals with the data and insight that help enhance their performance. Its AI learns which tactics separate a firm’s top-performing team members from the rest and then supports scaling that behavior across the entire team through real-time nudges, helping convert prospects more effectively, reduce turnover, and optimize portfolio performance.
That approach is delivering results. Grotto is already live with institutional operators including Weidner Apartment Homes, one of the largest apartment owners in the US. At Weidner, Grotto helped drive an 80% increase in lead-to-tour conversions, even with a highly trained team.
Our conviction in Grotto starts with its founders. Nick and Ben met while building large-scale AI systems at EvolutionIQ, an ICONIQ portfolio company, where they developed machine learning and language models for highly regulated, data-rich industries and helped lead the company to a $730 million acquisition in 2024, one of the earliest major vertical AI SaaS exits.
That experience shaped a shared belief: some of the most meaningful applications of AI happen close to the user, not to replace them, but to empower them. In our view, this belief is particularly important in real estate, where ample consumer choice means that the operators who focus on providing residents with a tailored, fundamentally human experience – one elevated beyond chatbot-based communications – tend to excel. We also believe that Grotto’s approach, melding AI-driven support with an altogether human “last mile,” drives positive externalities at a time when the potential impact of AI on employment looms large.
We believe Nick and Ben exhibit in spades the same combination of technical excellence, curiosity, grit, relentless execution, and leadership capacity that have characterized the successful founders in our portfolio.
Real estate is resilient, complex, and deeply human. We believe Grotto has the potential to make it more intelligent, efficient, and responsive, without losing sight of what makes it personal.
Published:
February 19, 2026
