How The World Works Mike Masnick
May 28, 2025
Kevin D. Williamson chats with Mike Masnick, founder and editor of Techdirt, who specializes in technology and civil liberties. They tackle the complexities of content moderation, weighing safety against freedom in diverse online spaces. Mike reflects on the internet's evolution from decentralized beginnings to its current state, emphasizing responsible technology use. They also highlight the Streisand Effect, showing how censorship attempts can backfire dramatically, and discuss using AI to boost writing productivity, showcasing its potential in creative workflows.
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Educator At The Tech-Law Crossroads
- Mike Masnick frames his work as educating people about the intersection of technology, law, and civil liberties.
- He uses writing, podcasts, papers, events, and games to make complex topics accessible.
Games To Teach Complex Policy
- Mike describes creating both boxed and in-person games to teach tech policy topics.
- He simulates large-group scenarios like elections to surface real-world tradeoffs.
Role-Play Breaks Ideological Blindspots
- Role-playing in games reduces preconceived notions and forces empathy with difficult operational decisions.
- That openness reveals why real trust-and-safety choices are more nuanced than public debates suggest.