Sam takes us through the development of "Roxanne," an AI chatbot created with Housing Court Answers and New York Law School to help NYC tenants understand their rights. It's a perfect full-circle moment from his early days in Australia where a weekend project to help people navigate unfair laws led to actual legal reform and later inspired Josef's mission.
We love how Sam cuts through the hype around legal AI. His team tested Roxanne with 100 housing attorneys trying to "break" the tool before launch – highlighting their practical, responsible approach. When we pushd him on the risks, Sam reframes that for most people seeking legal help, the alternative is "Google or nothing."
The conversation gets delightfully philosophical at times, especially when Sam challenges us on how people interact with AI interfaces. His approach of limiting chatbots to single-question interactions rather than ongoing dialogues sparked a fascinating tangent about human-AI relationships and expectations.
We particularly appreciate how Sam's pro bono work informs Josef's commercial products, creating a virtuous cycle of innovation that benefits both vulnerable communities and enterprise clients.
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