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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

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

Former U.S. Secretary of Transportation Pete Buttigieg is on the shortlist of Democrats expected to make a run for the White House in 2028. Six years ago, the then-mayor of South Bend, Indiana, burst onto the national political scene as the first openly gay major presidential candidate. His centrist appeal and platform of good governance helped him win the Iowa Caucuses, edging out independent Vermont Senator Bernie Sanders and then-former Vice President Joe Biden. But should Buttigieg choose to run again, he’ll face a much more fractured Democratic electorate that’s still divided over Gaza, the 2024 election, and the best strategy to counter the MAGA movement.

 

In a live conversation recorded at the University of Michigan’s Rackham Auditorium, Kara and Pete talk about his concerns over how the Trump administration is using the assassination of conservative commentator Charlie Kirk to crack down on free speech; why he and other Democrats struggle to speak clearly about the war in Gaza; and his vision for a post-Trump America. Buttigieg also weighs in on whether he is, in fact, planning to run for president again in 2028. Thanks to the Gerald R. Ford School of Public Policy 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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Pete Buttigieg on Biden, Trump, Gaza, and His 2028 Presidential Plans

For years, Senator Joe Manchin of West Virginia was a Democrat with a habit of voting against the party line. Not surprisingly, that was something many Democrats despised and Republicans relished. His resistance cost Democrats big legislative wins, including President Biden’s $1.75 trillion Build Back Better Act in 2021. After being called a DINO (Democrat in Name Only) for years, Manchin flirted with a presidential run on the No Labels ticket and officially dropped the “D” to become an independent in 2024, shortly before leaving office.

Kara talks to Manchin about his new memoir, Dead Center: In Defense of Common Sense, his reasoning for occasionally siding with the other side of the aisle, his defense of the filibuster, and why he thinks independents might have a better chance in 2028. 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube (full episodes available now!) Instagram, TikTok, and Bluesky @onwithkaraswisher.
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Joe Manchin on Trump, the Dems & the Filibuster

As more companies push AI in their workplaces, the technology is rapidly reshaping the way many of us do our jobs. But a lot of people — from entry-level employees to the C-Suite — are still in the dark about the limits of AI, its best uses, and how to make it work for them. 

We called in a panel of AI experts to answer some our listeners’ burning questions about how to use it at work: Sayash Kapoor, co-author of the book AI Snake Oil: What Artificial Can Do, What it Can’t, and How to Tell the Difference and the Substack AI as Normal Technology; Rajeev Kapur, CEO of 1105 Media and author of the book AI Made Simple: A Beginner's Guide to Generative Intelligence; and futurist and author Amy Webb, founder and CEO of the consulting firm Future Today Strategy Group.

Kara, Sayash, Rajeev and Amy break down everything from how vibe coding works to thornier questions around privacy and regulation. They talk about how young people can prepare themselves to enter the workforce, and how all of us can develop skills to stay relevant. And, of course, they weigh in on the question so many of us are asking right now: Is AI coming for my job? 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, and Bluesky @onwithkaraswisher.
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How To AI: A Practical Business Q&A With Three Experts

AI video generators are making storytelling more affordable — and one day, the tools may allow anyone with enough creativity to become a filmmaker. But the same technology can power convincing deepfakes that undermine our shared reality and destabilize our politics. 

Cristobal Valenzuela, the co-founder and CEO of Runway AI, joins Kara to discuss how its tools are disrupting the advertising and film industries, and why Hollywood studios might not want to admit how much they are using them. 

They also talk about how Runway is holding its own against (and warding off takeover advances from) much bigger tech players, and the AI video industry's responsibility in preventing deepfakes and political manipulation. Plus: Kara becomes a Top Gun pilot! Watch the video on the On With Kara Swisher YouTube page. 

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

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Is AI Hollywood’s Newest Star? Runway AI’s Vision for the Future of Film

In her latest book, We the People, the historian, New Yorker staff writer, and Harvard University professor Jill Lepore turns her attention to the history of the U.S. Constitution. Specifically, she focuses on all the ways our government’s foundational text has changed throughout its nearly 250 year history. Lepore calls Article V, which lays out the Constitution’s amendment mechanism, by far its most “radical innovation.” But she says the Constitution has become unamendable in the modern era — it hasn’t been meaningfully updated in more than a half-century, corroding our politics and government. 

Kara and Jill break down why the Framers included a way to make changes to the Constitution, how we’re still grappling with Article V’s bad compromises, and why the now dominant judicial philosophy of originalism contradicts the Framers’ intent. Lepore also digs into whether the Constitution can withstand PresidentTrump’s constant attacks.

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, and Bluesky @onwithkaraswishe
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How A ‘Brittle’ Constitution Broke U.S. Politics with Historian Jill Lepore

While media pioneer John Malone may not be a household name, he’s had a hand in shaping how all of us watch TV. Malone built Denver-based Tele-Communications Inc. into the largest cable company in the country, and then carved out Liberty Media from TCI. Liberty, along with various spinoff companies, have owned controlling stakes in companies like Discovery, SiriusXM, the Atlanta Braves, and Formula 1. Now, at 84, Malone has a new book out, “Born to Be Wired,” about his career and the fellow media titans he met along the way. 

Kara and Malone talk about how he transformed from the Ivy League-educated engineer to one of the “cable cowboys” who helped bring cable television into the homes of millions of Americans, how he squares his libertarian politics with President Donald Trump’s policies and the MAGA Republican Party, and why he thinks Big Tech needs major regulation. He also expands on some of his recent critiques of CNN and supposed left-wing bias in the media. 

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, and Bluesky @onwithkaraswisher.
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Liberal Media Bias, Trump & Taming Big Tech with Cable Impresario John Malone

Today, we’re re-airing one of Blakeney Schick’s favorite episodes: an interview with her former yoga student, comedian and writer, Mike Birbiglia. Aging, parenting by mortality and dying alone or kinless: these are just some of the uplifting topics Kara and Nayeema tackle before the interview. 

When we originally published this episode, Mike was deep in his latest Broadway show, “The Old Man and the Pool.” (The show completed its Broadway run in January, and will open for a limited run in London next month.) In it, Birbiglia doesn’t shy away from such heavy topics either. Birbiglia and Kara discuss mortality, parenthood, their last words and finding comedy in all of life — even the sad bits. 

Questions? Comments? Email us at on@voxmedia.com or find us on Instagram. We’re @karaswisher and @nayeemaraza.

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Aging, Death and other Uplifting Topics with Mike Birbiglia

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