Matthew Yglesias is a leading policy blogger and journalist, and has long pioneered what political media looks like on the internet. He has written about politics and public policy for a wide array of publications, including the American Prospect, the Atlantic, the Center for American Progress, and Slate. In 2014, Matt co-founded Vox with Ezra Klein and Melissa Bell, where he served as a senior correspondent. He left Vox in 2020 to start his own Substack, Slow Boring. Yglesias also released his third book in 2020, titled One Billion Americans: The Case for Thinking Bigger. More recently, Matt just launched his new podcast, ‘Bad Takes,’ which seeks to challenge extremely online political opinions. In our conversation, we seek to zoom out from the thrall of internet politics and look at Yglesias’ role in the current political media landscape. How does Matt use Twitter, and what does he think of its role in democratic discourse? What is the future of political media? What does the emergence of individualized media outlets, like Substack, suggest for that future? We transition briefly to some of the ideas that have arisen from our current political media landscape. In particular, how ‘real’ is the push for supply-side liberalism and the Abundance Agenda? Are online political pundits, bloggers, and analysts as responsible for its advent as it might seem? Finally, we ask Matt—a former college student—for his suggestions to current college students. How should they spend their time in school? And what careers should they look at afterward?