Season 7 of the No Cap podcast continues with Sammy Greenwall, co-founder and CEO of Henry AI.
Henry helps commercial real estate professionals create offering memorandums, BOVs, investment memos, and loan packages in a fraction of the time traditionally required. But the conversation quickly expanded into entrepreneurship, brokerage margins, data infrastructure, and where commercial real estate is heading as firms rethink how work gets done.
Conversation Highlights
Alex: Give us some of your background.
Sammy Greenwall: I grew up in the Bay Area around technology and small-scale real estate investing. After college, I joined Toll Brothers, where I spent an enormous amount of time building presentations for apartment and condo joint ventures.
I was as an analyst spending 70% of my time pushing things into PowerPoint and formatting.
Jack: So every day you’re having to put together a new deck. It’s almost the same thing, just a different deal.
Sammy: We were working on huge deals, but most of my day was spent formatting PowerPoint decks. That frustration stayed with me for years.
Alex: You don’t come from a technical background, right?
Sammy: I studied computer science classes in school, but I’m not technical relative to my co-founder Adam. After Toll Brothers, I got exposure to venture investing and proptech. We were investing in venture funds and technology companies, and I became fascinated by what these founders were building. I always knew I wanted to start a company myself.
Alex: What led to Lev?
Sammy: My sister connected me with Yakov Novik, and we ended up starting Lev together. The early days were chaotic, but we eventually scaled the company and raised significant capital.
There were literally two paychecks left.
Sammy: We got through that period, raised more capital, and eventually scaled the business. We raised a $30M Series A and later a $70M Series B. Looking back, it was a lot of hustle, a lot of luck, and a lot of learning on the fly.
The conversation then shifted from Sammy’s startup journey to the problem that eventually became Henry AI.
Alex: At what point did the idea for Henry get born?
Sammy: After leaving Lev, I kept coming back to the presentation problem I experienced earlier in my career. I realized technology could solve most of the workflow if humans handled the final layer.
Alex: What’s the bigger vision?
Sammy: We help brokers create institutional-quality OMs and BOVs in hours instead of weeks. But the bigger opportunity is helping brokerages operate more efficiently.
Jack: If someone can use Claude or ChatGPT, why do they need Henry?
Sammy: That’s the question every prospect asks. There’s a complete difference between generating a few slides and producing an institutional-quality deck that helps somebody win business. We pull in comparable transactions, company branding, market data, historical deals, and all the details that actually matter. Our average contract size is about $25,000 annually. There’s a reason customers are paying that instead of paying for a generic presentation tool. Software in itself will not be able to replace the entire services industry. But if you can build something using software that acts like a service, you can really build something big.
Later in the conversation, the discussion moved from brokerage workflows to what Sammy believes is the industry’s most valuable asset: data.
Alex: What are you seeing on the data side?
Sammy: Most brokerages already have valuable data. The challenge is that it’s trapped across emails, spreadsheets, PDFs, and internal systems.
Jack: So where does Henry fit into that?
Sammy: Long term, we want Henry to become the operating system that helps brokers win business and make better decisions.
Alex: What excites you most right now?
Sammy: The productivity gains are incredible. Tasks that used to take hours can now be completed in minutes.
The episode wrapped up with a broader discussion on entrepreneurship, productivity, and why the next generation of commercial real estate software may look very different from the tools firms use today.
Sammy: Someone has to build the rails between what these horizontal tools can do and how commercial real estate firms actually operate. We want to be that company.
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