On with Kara Swisher

• The Revenge Presidency with Maggie Haberman

  As the One Big Beautiful Bill Act lumbers through Congress, President Trump lobs threats at Russian President Vladimir Putin on Truth Social, and the administration continues its war against Harvard, we’re bringing back New York Times reporter and de facto Trump chronicler Maggie Haberman to weigh in on the president’s state of mind.  Kara and Maggie talk about the startling scale of disinformation coming out of the White House, Trump’s ambivalent relationship to Supreme Court rulings and democratic norms, and his ever-widening campaign of retribution against institutions and individuals, (including pop stars like Maggie’s favorite, Bruce Springsteen). They also revisit Haberman’s prescient analysis from earlier this year that Stephen Miller is wielding immense power within the administration and discuss whether Elon’s power is shrinking or he’s simply slipping out of public view.  This episode was taped on the afternoon of Tuesday, May 27th, before Elon Musk spoke out against the omnibus bill and Russia proposed to hold peace talks with Ukraine. Questions? Comments? Email us at [email protected] or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Can Smaller Startups Compete in the AI Race?

  Last year, AI and machine learning startups raked in about half of all VC funding in North America. And so far this year, AI is still leading the pack. But a huge chunk of the money in the Q1 — $40 billion — went to one player: OpenAI. So is there still room for smaller, more focused startups in the AI gold rush? Or will it be a case of “winner takes all?” In this live conversation at the Johns Hopkins University Bloomberg Center's inaugural Discovery Series, Kara speaks with Gary Rivlin, author of “AI Valley: Microsoft, Google and the Trillion-Dollar Race to Cash In on Artificial Intelligence,” and Christy Wyskiel, senior advisor to the president of Johns Hopkins University for innovation and entrepreneurship and the executive director of Johns Hopkins Technology Ventures. The three discuss the impact of government cuts on AI research, how small AI startups can compete with the tech giants, and how AI could revolutionize health care.  This interview was recorded on April 28, 2025. Questions? Comments? Email us at [email protected] or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Sam Altman, OpenAI and the Future of Artificial (General) Intelligence

  Few technological advances have made the kind of splash –– and had the potential long-term impact –– that ChatGPT did in November 2022. It made a nonprofit called OpenAI and its CEO, Sam Altman, household names around the world. Today, ChatGPT is still the world’s most popular AI Chatbot; OpenAI recently closed a $40 billion funding deal, the largest private tech deal on record. But who is Sam Altman? And was it inevitable that OpenAI would become such a huge player in the AI space? Kara speaks to two fellow tech reporters who have tackled these questions in their latest books: Keach Hagey is a reporter at The Wall Street Journal. Her book is called “The Optimist: Sam Altman, OpenAI and the Race to Reinvent the Future.” Karen Hao writes for publications including The Atlantic and leads the Pulitzer Center’s AI Spotlight Series. Her book is called “Empire of AI: Dreams and Nightmares in Sam Altman’s OpenAI.” They speak to Kara about Altman’s background, his short firing/rehiring in 2023 known as “The Blip”, how Altman used OpenAI’s nonprofit status to recruit AI researchers and get Elon Musk on board, and whether OpenAI’s mission is still to reach AGI, artificial general intelligence. Questions? Comments? Email us at [email protected] or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Barry Diller Unfiltered: on Family, Fortune, Elon, Trump & AI

  Barry Diller’s fingerprints are all over pop culture. From inventing the Movie of the Week and pioneering the television mini-series to launching the FOX broadcast network, redefining home shopping channels, and popularizing dating apps — Diller has had a hand in shaping the American experience for decades.  His memoir, Who Knew, takes readers from his difficult childhood through his meteoric rise in Hollywood and finally, his reinvention as a groundbreaking internet entrepreneur.  And although much of the press around the book has focused on Diller’s sexuality and his relationship to his wife, Diane von Furstenburg, nothing in his personal life is anywhere near as fascinating as his singular career. Kara and Barry discuss his life, his family, his approach to business, and his take on Trump and how to beat him. Questions? Comments? Email us at [email protected] or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• The Daily Show's Jordan Klepper Takes on Next-Gen MAGA and the Manosphere

  Few people have as much knowledge of the MAGAsphere as Jordan Klepper, co-host and correspondent for The Daily Show. Klepper has been covering President Trump and his supporters since the 2016 presidential campaign, from rallies across the country to the steps of the Capitol building on January 6, 2021. One difference that he — and others — have noted between Trump 1.0 and 2.0 is the growing number of young people, especially young men, who are now in the Republican fold. Kara talks to Klepper about his upcoming special, The Daily Show Presents: Jordan Klepper Fingers the Pulse: MAGA: The Next Generation, and what he learned about young conservatives on his tour of college campuses, UFC events, and Spring Break beaches. They discuss "manosphere" influencers such as Charlie Kirk, Andrew Tate, and Joe Rogan, which progressive voices (like Hasan Piker) might break through, and whether Hollywood and comedy are veering to the right. Questions? Comments? Email us at [email protected] or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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