The Enshitification of Big Tech: A Conversation with Cory Doctorow

Dave and Matt talk to author and activist Cory Doctorow about the utopian roots of Silicon Valley, where it all went wrong, and how we can fix it.

(image via Gregory Katsoulis)

Welcome to the podcast Organized Money. You can listen to today’s episode with author Cory Doctorow on Apple, on Spotify, or wherever you get your podcasts.

Occupy Wall Street once held a tribute to the the death of Steve Jobs. In that movement and others in the 2010s, like the Arab Spring, there was a belief in the revolutionary power of technology to connect social movements and change the world. We look back on that with not a little embarrassment.

How did Silicon Valley’s ideology go from utopian dreams to self-serving power grabs? David and Matt dive into the power dynamics of Big Tech with author, activist, and anti-monopoly advocate Cory Doctorow. They explore how Silicon Valley’s early ideals of openness and innovation gave way to corporate dominance, leading to what Doctorow calls “enshitification”—the systematic decay of platforms as they prioritize profits over users.

The conversation unpacks the monopolistic strategies of giants like Amazon and Google, the erosion of competition through regulatory capture, and the role of interoperability in breaking Big Tech’s grip. Check out more of Cory's writing here and pick up his new book Picks and Shovels, about the early days of personal computing, here.

Listen via Apple:

Or Spotify, or wherever you get your podcasts.

Another thing we’re doing this year is providing transcripts and video for every episode. Here is the video for our conversation with Cory, it’s a more unedited version of the podcast. The transcript is here.

Thank you so much for listening. If there’s a monopoly you’d like us to explore this year, or if you have anything else to tell us, please let us know by leaving a comment or by responding directly to this email.