Shava Nerad is the former Executive Director of the Tor Project, open source software that helps users protect their online privacy. She is currently CEO of Oddfellow Studios, and a frequent writer through Quora (where I met her) and on her Patreon site.

Today, we talk about her early days as the youngest female Chief Software Engineer at DEC and IT manager at MIT, how to manage and relate to very different people, how she won an argument with Richard Stallman, and how and why Tor came to be one of the most praised and reviled pieces of software in the world (often by the same people). Shava knows when to follow the rules and when to break them, and that turns out to be very valuable.