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The Gray Area with Sean Illing

It’s time to get weird

The Gray Area with Sean Illing

Vox Media Podcast Network

Society & Culture, News, Politics, News Commentary, Philosophy

4.610.8K Ratings

🗓️ 4 August 2025

⏱️ 62 minutes

🧾️ Download transcript

Summary

The internet was supposed to set us free. But somewhere along the way, it became a tool for surveillance, extraction, and control. What happened? And is there still time to reclaim the weird, untapped potential of the digital world? This week, Sean is joined by Douglas Rushkoff. He’s a media theorist, author of Survival of the Richest and Team Human, and host of the Team Human podcast. They trace the arc of the internet from its utopian beginnings to its corporate capture, and explore what it would take to build something different. Along the way, they talk about the loss of weirdness, the logic of capitalism, the dangers of scale, and the difference between systems thinking and systems feeling. They also reflect on whether it’s still possible to use technology to foster a more connected and communal life. Host: Sean Illing (@SeanIlling) Guest: Douglas Rushkoff, media theorist and host of Team Human We’d love to hear from you. Email us at [email protected] or leave a voicemail at 1-800-214-5749. Your questions and feedback help us make a better show. Watch full episodes of The Gray Area on YouTube. Listen ad-free by becoming a Vox Member: vox.com/members Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

Click on a timestamp to play from that location

0:00.0

Support for this episode comes exclusively from Upwork,

0:05.0

the world's largest human and AI-powered freelance marketplace helping businesses reimagine how work gets done.

0:11.0

Later in the show, we'll hear from a real-life Upwork customer,

0:15.0

a business owner who says that his company would not be what it is today without the professionals he hired using Upwork. You can see how Upwork is helping to reinvent work in the AI era at Upwork.com slash updates.

0:31.3

Not long ago, I watched a talk by Douglas Rushkoff called Weirding the Digital.

0:38.3

It was a eulogy for the early internet and the idea that it was going to make the world

0:43.5

smarter, more open, more connected.

0:47.8

I invited Douglas onto the show to chat about this talk and about how the chaos of the

0:53.9

early web was commodified and normified.

0:58.0

That's the conversation I wanted to have.

1:02.0

But what I got was so much more.

1:06.0

More expansive, more intense, more provocative, and more fun, really.

1:14.9

I'm Sean Elling, and this is the gray area.

1:21.6

Doug's a media theorist, author, and host of the excellent podcast Teen Human.

1:26.9

But more than that, he's a keen observer of the moment with a real gift for dissecting the system that shaped society.

1:35.5

It turns out his talk about weirding the digital wasn't just a eulogy.

1:41.8

It was more like a call to arms.

1:44.3

By weirding, he means rethink from top to bottom.

1:48.9

And by the digital, he really means everything.

1:53.3

And this conversation reflects that.

1:56.2

It is all over the place in the best sense possible.

2:00.9

And I'm excited for you to hear it.

...

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