Turning Vacancy into Value: Announcing Our Investment in Grotto AI

In the U.S. alone, billions of dollars are lost each year as apartments sit vacant, renters struggle to find homes, and owners struggle to find renters. Vacancy loss remains one of, if not the, top operational challenges for multifamily owners - and by extension, one of the top vectors for cash flow improvement. Yet the tools that exist today are either too narrow in scope or too focused on automation at the expense of the human relationships that ultimately drive leasing decisions.

What if, instead of replacing people, we used AI to amplify what great leasing professionals already do best: build rapport, understand nuance and close thoughtfully? Early customer data points to meaningful improvements in both engagement and conversion, reinforcing a simple truth: the right blend of AI and human judgment unlocks value in a massive market. High-performing agents convert leads at rates up to 10x better than their peers - not because they work harder, but because they excel at the critical human-to-human moments that matter most. Imagine a world where every leasing agent has access to the insights and behaviors of a top performer. 

That is the promise of Grotto AI. 

Today, we’re proud to announce our investment in Grotto AI, an AI-powered platform reinventing how multifamily operators reduce vacancy loss by supercharging their leasing teams. The software works alongside agents, helping them engage prospects more effectively, anticipate turnover, and convert more leads into leases. 

The team has analyzed millions of leasing interactions to uncover what truly drives conversion. The single strongest predictor that a call converts into a tour? An agent laughing with the prospect. The second strongest? Asking open-ended questions about the prospect’s life. In other words, human connection matters profoundly. 

Grotto recognized early that relationship-building is mission-critical to revenue performance. Rather than automating away those moments, it built technology designed to elevate them. At the core of the platform is a real-time coaching and guidance layer that analyzes leasing interactions, identifies the behaviors correlated with success and delivers actionable guidance during calls and tours. The result: leasing teams that improve performance faster with clear, quantifiable impacts on occupancy, revenue and NOI. 

Looking ahead, Grotto’s path is compelling. First, continue delivering measurable reductions in vacancy loss. Second, expand into renewals and broader lifecycle management tools. And ultimately, build the foundational AI layer that helps multifamily operators run more intelligently across investment, development, marketing and operations. With a deep understanding of what top performance looks like in real estate operations and equally deep insight into renter behavior and preferences, Grotto is well-positioned to become a system of intelligence for the multifamily ecosystem.

Grotto was co-founded by Nick Deveau and Ben Epstein, who previously worked together at EvolutionIQ (EIQ), where they built core AI platforms used across regulated insurance industries. At EIQ, Nick led the medical intelligence team, and Ben built the internal LLM development platform; together, they bring both technical depth and a remarkably grounded approach to applying AI to real-world problems. As a Series A investor in EvolutionIQ (acquired by NASDAQ: CCC), we at Asymmetric saw firsthand the principles that defined their success: relentless customer focus, clear ROI and agentic workflows that empower operators rather than replace them. We are excited to see Nick and Ben bring that same playbook to real estate.

We are pleased to partner alongside ICONIQ and industry veterans like Avi Dorfman (Co-founder of Compass Real Estate) and Caren Maio (Co-Founder of Funnel Leasing & Get100) to back Grotto AI as part of their $10 million seed round. Nick, Ben and the entire team (they're hiring!) are redefining a category by solving a real, enormous and quantifiable problem with AI that respects - and empowers - the humans on the front lines. This is a space where the combination of domain expertise, technical rigor and a human-forward philosophy will win, and we’re excited to support them as they scale this vision. 

Learn more about Grotto AI and their funding announcement here: 

Axios: Grotto Raises $10M to Cut Rental Vacancies

Businesswire: Grotto Raises $10M Seed Round to Supercharge Leasing Agents with AI

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Image credits: Grotto AI

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