Otto Zastrow

Otto Zastrow, who also goes by Otto von Zastrow, is co-founder and CEO of Midpage, a New York legal research platform for litigators with case law, statutes, regulations, a citator, and AI search tools. He came to law from robotics, not from a law firm.

Lawn Robots and Language Models

Zastrow's first startup, Navstack AI, built AI-powered lawn robots, and his deep learning work there was about helping a robot see where it was allowed to drive, he told The Geek in Review podcast in June 2025. He noticed that language models were improving faster than vision models and that consumer robotics was hard to bring to market.

At ETH Zurich his master's thesis applied language models to legal documents, the hosts noted. “I had a bunch of friends at law school or starting their first jobs,” he said, “and so I was acutely aware of the things that they get confronted with every day.”

A Kangaroo Court for Product Testing

Midpage runs a monthly internal “kangaroo court,” in which every employee, whatever their role, has to do real legal research with Midpage or traditional tools, he explained on the podcast. The goal is to make engineers and designers feel a litigator's pain points firsthand.

Owning the Data

In June 2025 Midpage raised a $4 million seed round, bringing total funding to $6.2 million, and launched Proposition Search, LawSites reported. Zastrow has stressed building Midpage's own case law dataset so the company is not beholden to incumbents, and Midpage's company page lists Perplexity, Litera, and BriefCatch among the companies that use its legal data.