AI deal-assistant for commercial real estate brokers — an OM/BOV/underwriting copilot that ingests brokers' own files and, longer term, aggregates that unstructured deal flow into a proprietary CRE data layer. The wedge is the workflow the incumbents ignored: CoStar sells data to owners and researchers; Henry sells time back to the broker who actually closes the deal. Insight from the founder: you cannot remove the broker from the transaction, so build for them and let the data compound.
Serial-founder team — Sammy Greenwall previously co-founded Lev and scaled it from 0 to Series B, $200M+ raised and $10M+ run rate; CTO Adam Pratt spent six years as an Engineering Manager at Zocdoc and previously sold Halligan for a low-seven-figure exit (source: 2024-09-17 note, rec6OeRkkg3uvo0ZK). At the time of the SH check the company had $115K ARR across seven paying customers and was in YC S24; the round was "basically closed" and StoryHouse was let in for a $100K allocation on the $4M / $19M-cap SAFE. SH committed $100K via StoryHouse Fund I at a $19M cap, alongside Susa Ventures and 1Sharpe Ventures (co-leads), plus YC.
The addressable stack is the CRE software market, but the sharper frame is the broker segment — the smallest slice by revenue and the fastest-growing (analysts peg the agent/broker sub-segment at >12% CAGR) because it has historically been the most under-tooled. Generative AI collapses the OM/BOV/underwriting workflow from weeks to minutes, which is precisely what Henry sells. The timing question is not demand — it is whether the incumbent stack (CoStar, ARGUS, Buildout) or a startup wins the AI-native rewrite.
| Player | Positioning | Funding / Stage | Edge vs. them |
|---|---|---|---|
| Henry AI | AI copilot for CRE brokers: OMs, BOVs, comps, underwriting from drag-and-drop files Internal | Seed $4M @ $19M cap; Series A $85M post Internal | — |
| CoStar Group | Dominant CRE data/listings platform; acquired Matterport (Feb 2025, $1.6B) to add 3D + AI Web | Public, ~$30B+ mkt cap | Broker-first workflow vs. data-vendor mindset; ships product weekly |
| CompStak | Crowd-sourced CRE lease/sale comps for brokers, appraisers, researchers Web | Growth-stage private | Data-only vs. Henry's deck/underwriting output |
| Reonomy | Property intelligence, ownership graph, off-market discovery Web | Private, growth stage | Prospecting layer vs. deal-execution layer |
| Buildout / ARGUS | Marketing/CRM (Buildout) and cash-flow modeling (ARGUS) — legacy tools brokers already own Web | Private, mature | Single AI surface replaces multi-tool stitching |
Moat: the flywheel the founder is explicit about — every deck ingested is proprietary CRE data that brokers willingly hand over; over time that data layer is defensible in a way the workflow features are not.
Natural acquirers are the CRE data/platform incumbents rebuilding on AI: CoStar (which just paid $1.6B for Matterport Web), Altus Group (owns ARGUS + Reonomy), MRI Software, or a public brokerage (CBRE / JLL / Colliers) buying broker-productivity IP. PropTech M&A ran to 163 announced deals YTD through Nov 2025 with $6.8B in disclosed value, so the exit window is active Web. Return math: at a $19M entry cap, a mid-9-figure strategic exit lands in the 20–40x fund-returner range, which is why a $100K allocation was worth taking.
First call with Sammy after LinkedIn / Sales Nav cold outreach. Round already led by Susa and 1Sharpe at $19M cap and effectively closed, but Sammy offered SH a $50–100K allocation.
Intro / intel source: LinkedIn Sales Nav + cold outreach.
Deal status: In Conversation.
Next steps: Discuss in IC. Round is basically closed but said they would let us write a $100K check if we wanted to, but wouldn't accept any more.
Summary of call: Great call with Sammy. Have been trying to get ahold of him since his time at Lev. Very strong founders in a massive market. $4M round led by Susa Ventures and 1Sharpe at $19M cap.
Team & founders — Sammy: Did one year at Pomona junior year via the transfer program; Swarthmore College 2018 grad. Former intern at Tuesday Capital. Worked a capital-markets role at Toll Brothers. Previously founded Lev; over 5 years took them from 0 to Series B, raised $200M+, hit $10M+ run rate.
Team & founders — Adam Pratt (CTO): 6 years as Engineering Manager at Zocdoc. Previously sold his startup Halligan for a low-seven-figure exit.
Company: Gen-AI for commercial real estate professionals — a deal assistant designed to help CRE brokers close deals. In the current YC batch. Brokers use Henry to generate OMs, BOVs, comps analysis, market summaries, cash-flow models, LinkedIn deal announcements. Henry extracts and labels unstructured real estate data; brokers just drag and drop files.
Insight / secret sauce: You cannot remove the broker, so build software for them. The long-term vision is a Bloomberg terminal for CRE data — the company ingests the deal files brokers willingly share and generates automated output, and over time uses that data to become a proprietary CRE dataset.
Market & competitors: Positioned against CoStar.
Traction: $115K of ARR across 7 paying customers.
Round dynamics: Raised $4M from Susa and 1Sharpe at $19M cap. Have stopped accepting commitments but would take a $50–100K check from SH.
Lead investors: Susa Ventures and 1Sharpe Ventures. Round terms: $4M on $19M cap.