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Vox Media

It's on. Twice a week, award-winning journalist Kara Swisher gets to the heart of the story through no-holds-barred interviews with power players across business, tech, media, politics and beyond. So why do her guests show up? “Smart people,” says Kara, “like difficult questions.”
Mondays and Thursdays from New York Magazine and the Vox Media Podcast Network.

On with Kara Swisher

From an early age, writer, director, and producer Judd Apatow has been obsessed with comedy. What started as a quest to interview comedians for his high school radio station ultimately evolved into one of the most prolific careers in Hollywood today, with hits like “The 40 Year Old Virgin,” “Knocked Up,” and “Anchorman.” Now, Apatow is looking backwards. His new book, “Comedy Nerd,” is a visual memoir of his decades in the business, working with a who's who of the biggest names in comedy. 

Kara and Judd talk about how he reimagined the genre of raunchy, R-rated comedies about stunted adolescence; what he got right about American masculinity in the mid-and-late 2000s; and his recent pivot to making documentaries about some of the greatest comedians of the modern era. They also discuss whether AI can be funny and the ways politics is shaping comedy right now. 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.
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Judd Apatow on Meme Politics, Being Funny in 2025 & the Comedy Biz

When the Department of Justice has to investigate politically sensitive matters, those investigations are typically handled by outside prosecutors known as Special Counsels: independent investigators given the freedom to unearth the dirtiest dirt against executive branch officials, including the president. 

Kara speaks with CNN senior legal analyst, former prosecutor, and best-selling author Elie Honig about his latest book, When You Come at the King: Inside DOJ’s Pursuit of the President, from Nixon to Trump. They discuss the history of the DOJ’s independent investigations, the Trump administration’s current (and mostly successful) attempts to weaponize the DOJ, the Supreme Court’s presidential immunity ruling, and recommendations for fixing the system. 

Want to see Kara and Scott Galloway live during the Pivot Tour November 8th-14th? There are still limited tickets available. Go to PivotTour.com for details.

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.
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Inside Trump’s DOJ Power Play & the Future of Special Counsels

In the wake of President Trump’s return to the White House, independent Vermont Sen. Bernie Sanders spent months crisscrossing the nation rallying huge crowds in red and blue states during his Fighting Oligarchy tour. His new book, “Fight Oligarchy,” is an extension of those rallies and also serves as a blueprint for how everyday Americans can push back against the deep-pocketed forces shaping politics today. But at 84 years old, the two-time presidential candidate is also looking to the future of the progressive movement he helped build. 

Kara and Sen. Sanders talk about his headline speech at this weekend’s No King’s rally in Washington, D.C.; the corrosive effects he thinks billionaire donors have on the Democratic Party; and the ongoing government shutdown. They also chat about how he’s getting involved early in next year’s midterm elections to help boost progressive candidates — both Democrats and independents like him — in races across the country. 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.
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Bernie Sanders on Beating Authoritarianism, Billionaires & AOC

Will artificial intelligence be a job creator or a job destroyer? Who will be most affected — and how long will the AI revolution in employment take? 

Futurist Martin Ford and economist Betsey Stevenson join Kara to unpack the realities behind the AI hype. They explore the impact of artificial intelligence on the future of work, from the fate of blue-collar jobs amid advancing robotics to the government’s role in helping workers navigate this new era. They also dive into ideas like universal basic income and a digital dividend, and examine how AI could redefine our economy, society, and the role work plays in a meaningful life.

Martin Ford is the founder of a software development firm and the author of four books, including the New York Times bestselling Rise of the Robots: Technology and the Threat of a Jobless Future.

Betsey Stevenson was the chief economist of the US Department of Labor from 2010 to 2011, and then served on the Council of Economic Advisors from 2013 to 2015. She's a professor of Public Policy and Economics at the University of Michigan and serves on the executive committee of the American Economic Association.

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Want to see Kara and Scott Galloway live during the Pivot Tour November 8th-14th? Get tickets and details at PivotTour.com. 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.
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How AI Will Impact the Future of Work

Former Vice President Kamala Harris joined Kara to talk about her new book, “107 Days,” in front of a packed house at the Warner Theatre in Washington, D.C. They discussed President Trump’s weaponization of the Justice Department, the tech industry’s rightward shift, and how to combat Trump’s march toward autocracy in an age of disinformation, blatant power plays, and political exhaustion.

Want to see Kara and Scott Galloway live during the Pivot Tour November 8th-14th? Get tickets and details at PivotTour.com. 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.
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Kamala Harris on Trump, Tech’s Power Grab, and the Fight for Democracy

Acclaimed researcher, podcaster and best-selling author Brené Brown joins Kara to unpack her vision of leadership, as outlined in her latest book, "Strong Ground." They discuss the dangers of "power over" leadership, why courage and vulnerability are essential traits for real leadership, and how turbulent times can pave the way for bad leadership. They also explore the impact of AI on human connection and the challenges faced by leaders in navigating a world of uncertainty and paradox. Brown shares her research on the self-conscious effects of shame and humiliation, and both she and Kara reflect on the qualities of effective and ethical leadership.

Want to see Kara and Scott Galloway live during the Pivot Tour November 8th-14th? Get tickets and details at PivotTour.com. 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.
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Brené Brown on the State of Leadership in America Today

In the late 80s and early 90s, makeup artist Bobbi Brown made a name for herself by pioneering a more natural look long before it became the dominant trend. She eventually turned her side hustle selling lipstick out of her house in suburban New Jersey into a billion-dollar eponymous makeup brand that changed the beauty industry. But her unceremonious exit from parent company Esteé Lauder, with approximately four years left on a 25-year noncompete clause, stripped her of the company she had built over decades and sidelined her from the industry. 

Now in her 60s, Brown has started over with a new makeup line called Jones Road, and she’s telling her story in a memoir, “Still Bobbi: A Master Class in Resilience and Reinvention.” 

Kara and Brown talk about how she changed the makeup industry and founded a second successful company, plus where she sees the beauty industry headed in the era of influencers and social media. 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.

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Makeup Mogul Bobbi Brown on Reinventing Herself in Her 60s

Universities have been in the crosshairs of the White House since President Trump took office — and Princeton University president Christopher Eisgruber is one of a handful of college administrators who have spoken out against it. 

Kara speaks to the Eisgruber about his new book, Terms of Respect: How Colleges Get Free Speech Right, and right-wing attacks on universities that come under the guise of free speech, including from the late conservative activist Charlie Kirk and his organization Turning Point USA. They discuss why some campus leaders have fought against (and others have complied) with the Trump administration’s investigations into allegations of antisemitism and demands to overhaul diversity programs in college admissions and hiring. And they talk about the long-term impacts of losing academic freedom on the reputation and success of US higher education, the economy and society as a whole. 

Please note: this interview was recorded on Monday September 29th, before President Trump said his administration was nearing a deal with Harvard while it also began a process called debarment that could allow it to bar the university from future federal grants. 

Want to see Kara (and Scott Galloway) live on the Pivot Tour November 8th - 14th? Find tickets and details at PivotTour.com. 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.

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Free Speech, Colleges & Trump with Princeton President Chris Eisgruber

At age 67, Sen. Tina Smith (D, MN) is doing something that’s still rather rare for senators: retiring at a relatively young age, after just one full term in office. Smith’s open Senate seat is one of five Democrats will have to defend in next year’s midterm elections, in what’s shaping up to be a tough cycle. But with a little more than a year left in office, she still has to work on the big problems facing the Democratic Party, and the nation more broadly, including a rise in political violence and this week’s looming government shutdown. 

In a live conversation recorded Saturday at the annual MinnPost Festival in downtown Minneapolis, Kara and Smith talk about why she thinks Democrats shouldn’t cave to Republican demands to keep the government open; how more of her colleagues should opt to retire instead of run for re-election; and what Democrats need to do to come out ahead in next year’s midterm elections. Smith also reflects on the recent spate of political violence, including the assasination of her friend and fellow Minnesota Democrat, Melissa Hortman, in June. (The gunman reportedly included the senator on his hit list.) 

Thank you to MinnPost for hosting this conversation. 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.
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Sen. Smith on the Shutdown, Democrats’ Future, and Retiring Early

Matt and Maria Raine say their son, 16-year-old Adam Raine, started using ChatGPT-4o in September 2024 to help with his homework. After Adam died by suicide this past April, his parents realized that ChatGPT was also lending an ear to Adam’s suicidal ideations and giving him advice on techniques. In a lawsuit filed against OpenAI and its CEO Sam Altman, the Raines allege that the chatbot actively isolated Adam from family and friends. They say ChatGPT not only didn’t stop Adam from taking his own life — it actually helped him do it.

Kara speaks to Matt and Maria, as well as their attorney, Jay Edelson of Edelson PC, about Adam’s final months, why they believe OpenAI and CEO Sam Altman should be held responsible for Adam’s suffering and death, and what kind of safety features are needed for AI companions. 

In response to a request for comment, an OpenAI spokesperson said: “Our deepest sympathies are with the Raine family for their unthinkable loss. Teen well-being is a top priority for us - minors deserve strong protections, especially in sensitive moments. We have safeguards in place today, such as surfacing crisis hotlines, guiding how our models respond to sensitive requests, and nudging for breaks during long sessions, and we’re continuing to strengthen them. We will soon roll out parental controls, developed with expert input, so families can decide what works best in their homes, and we’re building toward a long-term age-prediction system to help tailor experiences appropriately.”

This episode discusses the death by suicide of a teenager in significant detail. If you are struggling, please reach out for help. In the US and Canada you can call or text the National Suicide Prevention Lifeline at 988 anytime for immediate support. 

This episode version has been updated with a revised introduction.

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.
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Did ChatGPT Encourage a Teen Suicide? The Parents Suing OpenAI Say Yes

“Not my type” is what President Donald Trump said about writer and former advice columnist E. Jean Carroll after she accused him of sexually assaulting her in a dressing room at Bergdorf Goodman. Despite his denials, in 2023, a jury found Trump liable for assault and defamation and awarded Carroll $5 million. After he continued to defame her — leading his supporters to launch an avalanche of threats against her — a second jury in 2024 awarded Carroll $83.3 million in damages. 

Kara talks to Carroll and her lead attorney, civil rights lawyer Roberta Kaplan, about the two civil lawsuits Carroll details in her new memoir, “Not My Type: One Woman vs. a President.” They discuss potential evidence left out of the trial, including connections to Jeffrey Epstein, where Trump’s appeals stand, what chance he might have of bringing the cases to the Supreme Court and what impact his attempts to silence lawyers could have on our legal system.

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, and Bluesky @onwithkaraswisher.
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Making Trump Pay with E. Jean Carroll and Roberta Kaplan

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