On with Kara Swisher

• Makeup Mogul Bobbi Brown on Reinventing Herself in Her 60s

  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 [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Free Speech, Colleges & Trump with Princeton President Chris Eisgruber

  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 [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Sen. Smith on the Shutdown, Democrats’ Future, and Retiring Early

  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 [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Did ChatGPT Encourage a Teen Suicide? The Parents Suing OpenAI Say Yes

  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 [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Pete Buttigieg on Biden, Trump, Gaza, and His 2028 Presidential Plans

  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 [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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