FREE SPEECH FRIDAY 

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For the first time in fifteen years, there’s a real shot at ending billionaire control of American politics. 

A groundbreaking legal effort spearheaded by Harvard law professor Lawrence Lessig, backed by an unlikely coalition of billionaires like Mark Cuban and Reid Hoffman, is taking direct aim at the legal foundation that created Super PACs. 

I'm going to be covering this legal fight closely. Larry Lessig joined me on this week's Free Speech Friday to break down his legal fight, where things stand, and what needs to happen next in order to win this fight. 

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Over the past two decades, Taylor Swift has dominated the pop charts and risen to the pinnacle of mainstream fame. She has amassed a $2 billion fortune, won 14 Grammy Awards, sold more than 100 million albums worldwide, headlined the highest-grossing concert tour in history, and built a vast real-estate and music catalog empire.

But lately, the backlash to Swift is growing louder. She has been criticized for her silence on major political issues, for palling around with Trump supporters, her carbon footprint, and many are calling her latest album a flop. 

All of this raises the question, has Taylor Swift peaked, not just in popularity, but in cultural authority? Or is this just another cynical reinvention that she'll use to amass even more money and power? Journalist and Swiftie Kat Tenbarge joined me to discuss it all. 

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FREE SPEECH FRIDAY 

Last weekend, popular cosplay Twitch streamer Emiru was assaulted at a meet-and-greet during Twitchcon. A man cut across several meet and greet lines and attempted to grab her for a kiss. The incident was obviously a catastrophic failure when it comes to keeping women creators safe

But, after the Emiru incident, tons of big content creators began piling on on Twitter, pushing out of context clips attempting to show lax security at the event and calling for Dan Clancy's resignation. They began weaponizing the attack on a woman creator to push their own reactionary agendas. 

Kat Tenbarge has been covering gender-based violence for nearly a decade and she joined me this week to break down what exactly went down at Twitchcon, why more security doesn't exactly lead to more safety for women, and what the true issue at the heart of all of this is. These attacks on women creators silence women and prevent them from speaking and expressing themselves freely. 

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As live-streaming becomes an increasingly dominant form of entertainment, Twitch is at a crossroads. Dan Clancy is the CEO of Twitch, and I sat down with him this weekend at Twitchcon to discuss how Twitch is evolving, its broader role in the creator economy over the next 10 years, competition from Hollywood, AI, and how he thinks about balancing streamers' creative freedom with safety concerns. Here's our interview.

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Welcome back to Free Speech Friday!

Recently, Trump signed a little-noticed national security directive identifying a slew of views like “anti-Christian” and “anti-American” beliefs as indicators of "radical left violence" and terrorism. The directive is called NSPM-7. 

NSPM-7carries serious implications for freedom of speech and opens the door to dangerous levels of censorship. In NSPM-7, Trump directs the Justice Department, the FBI, and other national security agencies to fight his version of political violence, retooling a network of Joint Terrorism Task Forces to focus on “leftist” political violence in America. 

Ken Klippenstein has been covering all this. He joined me today to break down NSPM-7 and what it means for speech in America. Under the new directive, anyone expressing views that could be construed as any of the following, could be classified by the government as a terrorist:

• anti-Americanism,

• anti-capitalism,

• anti-Christianity,

• support for the overthrow of the United States Government,

• extremism on migration,

• extremism on race,

• extremism on gender

• hostility towards those who hold traditional American views on family,

• hostility towards those who hold traditional American views on religion, and

• hostility towards those who hold traditional American views on morality.

Ken's story: https://www.kenklippenstein.com/p/trumps-nspm-7-labels-common-beliefs

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Hasan Piker has never abused his dog, but you'd never know that from the video clips spreading all over the internet. The backlash that Piker is facing shows the consequences of a world where everyone is constantly being recorded and our internet is built to reward outrage and controversy. 

In this episode, I dive into the recent viral conspiracy and false claims about Piker and Kaya, unpacking how a single, out-of-context clip spiraled into a full-blown harassment campaign, fueled by bad actors and politically motivated smear tactics. 

I unpack how the Hasan Piker dog collar incident is a warning sign of a dystopian future where 24/7 video surveillance merges with online outrage farming. As AI and algorithmic amplification make it easier to manipulate and weaponize video, the problems influencers face today will soon affect us all.

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We're facing a tsunami of AI-generated music that is rapidly transforming the digital soundscape and expanding far beyond Spotify. It's already beginning to dominate platforms like YouTube, SoundCloud, and other major streaming services. Generative tools are able to produce entire songs complete with realistic vocals, melodies, and high production quality. AI artists are flooding recommendation algorithms and trending charts.

Kieran Press Reynolds is a writer at Pitchfork, and he's been covering all of this. He joined me to talk about the rise of AI music and what deepfake vocals, manufactured sounds and this flood of AI generated content means for the future of the music industry and the role music plays in our culture. 

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ICE is preparing to deploy a sweeping new surveillance system that would allow it to monitor the real-time movements and online activity of millions of people. Internal documents. The two key tools, Tangles and WebLoc, were originally designed by the Israeli intelligence firm Cobwebs.  Together, they enable ICE analysts to fuse billions of mobile location points with data scraped from platforms like Facebook, TikTok, and Reddit to build detailed digital dossiers on anyone. 

This expansion of ICE’s data surveillance efforts comes amid broader federal initiatives to monitor social media and suppress dissent. Reports indicate ICE will contract private analysts to continuously scan major platforms for “anti-American” or “anti-Christian” speech under the Trump administration’s new NSPM-7 directive. This is yet another dangerous escalation of mass surveillance and political targeting, undermining First and Fourth Amendment protections. 

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Nearly a decade ago, Ross Ulbricht, the founder of the Silk Road dark web marketplace was sentenced to a double life sentence in prison. Now, he's out and has become a powerful influencer and political figure in the MAGA movement.

Ryan Mac at the New York Times has been covering Ulbricht for over a decade. He joined me to dive deep into Ulbrict's' past, how the Silk Road transformed the web, and how this crazy alliance between bitcoin billionaires, libertarians, and MAGA die-hards has skyrocketed Ulbricht to fame and set him up for a major role in politics.  

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READ RYAN'S FANTASTIC NYT STORY: https://www.nytimes.com/2025/09/07/technology/ross-ulbricht-silk-road-comeback.html

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A VPN hides your IP address, making it harder for hackers, corporations and the government to track your activity. Most people know VPNs as a way to get around geogating (like if content is banned in one country you can use a VPN to get around the ban).

But as authoritarian governments in places like America and the UK seek to crack down on online speech, VPNs are under attack. It's getting harder and harder to use them effectively, and recently there's even been talk of an outright ban. 

Lia Holland is an activist at Fight for the Future, a civil liberties group fighting to protect VPN access. She joined me to dig into the political campaign against VPNs and talk about how to fight back. 

PS: A lot of VPNs are owned by Israel!! Or they trap you into subscription plans. Be careful before downloading one, here's a guide from the EFF on VPNs: https://ssd.eff.org/module/choosing-vpn-thats-right-you

Fight For the Future's Defend VPNs campaign: https://www.defendvpns.com 

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