The Billionaire Who Took America Online

The Billionaire Who Took America Online

Kara and Steve Case go back — way back, to the 1990s. She was a young Washington Post reporter covering a new thing called “the Internet” … and he was a co-founder of the company that became AOL. In this conversation, they take a walk back through time to look at how far the world has come and where tech companies have stumbled or fallen flat. They discuss Case’s new book, “Rise of the Rest,” which offers an optimistic future for the expansion of entrepreneurship and innovation beyond a handful of places like Silicon Valley, Boston and New York City. They also discuss whether a more equitable distribution of economic growth is possible, given some of the nation’s political divides — and potential solutions for bridging those divides. Before the interview, Kara and Nayeema talk about the newsmakers of the day, including Theranos founder, Elizabeth Holmes, who is seeking a new trial, and the deep pockets of “anti-woke” investors in Silicon Valley including, of course, Peter Thiel. As always, Kara offers unsolicited advice. Do you want some (solicited) advice from Kara? Call 1-888-KARA-PLZ and leave a message. You can find Kara and Nayeema on Twitter @karaswisher and @nayeema. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Driverless Semi-Trucks Are Here & Coming to a Highway Near You

Driverless Semi-Trucks Are Here & Coming to a Highway Near You

Kara sits down with Chris Urmson, CEO and co-founder of the autonomous trucking company Aurora, and Johnathon Ehsani, a professor of public health at Johns Hopkins University and leading road safety r...

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The Long Game with Jake Sullivan and John Finer

The Long Game with Jake Sullivan and John Finer

Happy Holidays from the On with Kara Swisher team! To celebrate, we’re gifting you a recent episode of a new national security podcast from the Vox Media Podcast Network. “The Long Game” is hosted by ...

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Winners, Losers & WTF Moments: A Look Back at 2025’s Top Tech Stories

Winners, Losers & WTF Moments: A Look Back at 2025’s Top Tech Stories

From an unenforced TikTok ban and a chatbot calling itself MechaHitler to mounting fears that we’re in an AI bubble, 2025 was another messy year for the tech industry. We watched billionaire CEOs full...

22 Dec 20251h 3min

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The End of Human Driving? with Uber CEO Dara Khosrowshahi

Kara sits down with Uber CEO Dara Khosrowshahi to dig into how applied artificial intelligence works at scale.  At Uber, AI powers everything from pricing, routing, and customer service to autonomo...

18 Dec 202547min

Sam Harris on Silicon Valley’s Slide into Techno-Authoritarianism

Sam Harris on Silicon Valley’s Slide into Techno-Authoritarianism

One of 2025’s most memorable images was of Silicon Valley’s billionaire CEOs lined up in the front rows at President Donald Trump’s inauguration. It was visual proof of the tech industry’s embrace of ...

15 Dec 20251h 3min

Rachel Maddow on Japanese Incarceration During WWII, Mass Deportation & Media Chaos

Rachel Maddow on Japanese Incarceration During WWII, Mass Deportation & Media Chaos

Rachel Maddow is an author, podcast host and producer, documentary producer, and, of course, the anchor of her eponymous show on MS NOW. Her newest podcast, "Rachel Maddow Presents: Burn Order," unrav...

11 Dec 202556min

Beyond ‘The Handmaid’s Tale’: Margaret Atwood on Memoir, Grudges, & Getting Older

Beyond ‘The Handmaid’s Tale’: Margaret Atwood on Memoir, Grudges, & Getting Older

Margaret Atwood is one of the most famous and prolific authors of the modern era. Though best known for her 1985 hit “The Handmaid’s Tale,” her dozens of works span literary genres — poetry, novels, c...

8 Dec 20251h 9min

Tech Billionaires & the Rural Poor: Two Sides of Trump’s MAGA Populism

Tech Billionaires & the Rural Poor: Two Sides of Trump’s MAGA Populism

The tech billionaires of Silicon Valley and the Midwestern rural poor wouldn’t seem to have much in common. But somehow many of them have united under the MAGA umbrella. Kara brings together two repor...

4 Dec 20251h 5min

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