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 fully align themselves with President Trump, Nvidia become the first $5 trillion company, and Elon Musk’s popularity tank, thanks to his DOGE antics (and yet he could still become the world’s first trillionaire).  Kara breaks down the biggest tech stories of 2025 with four journalists: Bill Cohan, a longtime financial journalist, author, and Puck co-founder who covers Wall Street; Casey Newton, founder and editor of the tech newsletter Platformer and host of The New York Times podcast “Hard Fork”; Joanna Stern, senior personal technology columnist for The Wall Street Journal and author of a forthcoming book about how she surrendered her life to A.I. for a year; and Charlie Warzel, staff writer at The Atlantic and host of the tech and culture podcast “Galaxy Brain.”  (Please note, this conversation was recorded before news broke that TikTok had signed a deal to spin off its U.S. business to a group of American investors, the Justice Department released a trove of documents tied to investigations into Jeffrey Epstein, and Waymo halted service in San Francisco because of power outages in the area.)  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

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 autonomous vehicles and sidewalk robots that deliver food. It has partnered with more than 20 autonomous vehicle manufacturers, and it’s moving aggressively into robotaxis. And although it may take many decades, Khosrowshahi believes society may eventually decide humans aren’t safe enough to be trusted behind the wheel. Kara and Dara discuss what this all means for jobs, congestion, climate and Uber’s business model.  This conversation was recorded live at the Johns Hopkins University Bloomberg Center as part of its Discovery Series on artificial intelligence.   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

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 MAGA’s authoritarian-style of politics — one it has benefited from considerably over the last year. Author and neuroscientist Sam Harris has been using his podcast, “Making Sense,” to talk about the ways tech moguls are corroding our politics, and although he used to be close with some of them, he’s become a vocal critic of their support for Trump. Kara and Sam talk about why he thinks the left is to blame for the tech billionaires’ shift to the right, why all of us are bad at sorting through the glut of information we find online, and the potential risks that come with the Trump administration’s hands-off approach to A.I. They also talk about what possible tech regulation could look like, and whether everyday people stand a chance against tech oligarchs and their platforms.  (Please note: This interview was recorded before President Trump signed an executive order to block states from passing A.I. regulation.) 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

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," unravels how the incarceration of more than 100,000 Japanese Americans and Japanese immigrants during WWII was planned and carried out. Shockingly, the full story behind one of the 20th century’s worst American human-rights abuses might never have come to light if not for the relentless work of a hobbyist researcher — who had been incarcerated herself. Kara and Rachel dig into the story and explore the parallels to President Trump’s mass-deportation policies. They also discuss the recent boat strikes on alleged drug traffickers, the escalating drama around the competing bids for Warner Bros. Discovery and what it signals for the future of the news business, and MSNBC’s evolution into MS NOW. Please note: This episode was taped on Tuesday, before President Trump said it was “imperative that CNN be sold." 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

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, children's books, essays, short stories — and often defy neat categorization. Now, at 86, Atwood has written her first memoir. At roughly 600 pages, it’s an intimate look at the ways her personal life inspired and shaped her writing.  Kara and Atwood talk about her lifelong passion for the outdoors, how she decided to become a poet when she was just a teenager, and her reputation for having an eerie prescience about major world events. They also talk about Atwood’s fears about the Trump administration’s use of power, and why she still considers herself to be a hopeful person despite her predilection for dark stories.  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

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 reporters who have written about the opposite sides of the MAGA coin to talk about the role of social media in fueling enragement, why tech billionaires and poor Americans are coalescing around issues like education, the press and more; and how to bridge the political divide. Her guests are: Beth Macy, a newspaper reporter for three decades and the author of five non-fiction books, including her most recent: Paper Girl: A Memoir of Home and Family in a Fractured America. Jacob Silverman, an independent journalist with a focus on tech, political corruption and illicit finance. He’s written three books, including his most recent: Gilded Rage: Elon Musk and the Radicalization of Silicon Valley.  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

How do you grieve the impending death of a lifelong friend when you are a multi-hyphenate comedian, actor, director and producer? If you are Tig Notaro, you produce a film about their life and work — as she has done for the late spoken word poet Andrea Gibson with the documentary Come See Me In The Good Light. Best known for her dry-witted stand up comedy, Tig is also a podcaster (Handsome), actor (Star Trek: Discovery, The Morning Show), director (Am I Ok?) and producer for film and television. Kara and Tig discuss the documentary, Gibson’s life and relationship with their wife Meg Falley after they were diagnosed with incurable cancer, how Andrea’s death opened her up to experiencing grief in a new way, and how it all relates to Tig's own 2012 cancer diagnosis, which she shared on stage in a genre-breaking set. Plus: how the comedy world is shifting under Trump and Tig’s plans for an all-lesbian action film. 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

In the mid-2010s, television journalist and former chief White House correspondent Jessica Yellin left her job at CNN to go independent. A few years later, she founded News Not Noise, a multi-platform news outlet that publishes all across the internet  (mainly on Substack, Instagram and YouTube). It made Yellin one of the first journalists to ditch mainstream media for social media, and it’s given her a unique perspective on the challenges and opportunities facing independent journalists, newsfluencers, and content creators in a crowded media environment.   In a live interview hosted by the Center for Journalism Ethics at the University of Wisconsin–Madison, earlier this fall, Kara and Jessica talk about what it takes to be a successful online news creator, the effects President Trump’s attacks on fact-based journalism have had on the news business as a whole, and how news creators can adapt to changing social media algorithms and AI. They also talk about solutions that could help the entire news industry in an era of waning public trust.  Please note: This conversation was recorded before X rolled out a new transparency location feature, revealing some prominent pro-MAGA accounts are not based in the U.S. despite claims on their profiles.  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

In the year since President Trump won re-election — thanks in part to capitalizing on sitdowns on friendly podcasts — Democrats have been looking for their own answer to the so-called “manosphere.” One of the top contenders has emerged from an unlikely place: bright red Oklahoma. That’s where Jennifer Welch and Angie “Pumps” Sullivan started their hit podcast, “I’ve Had It.” They’ve interviewed some of the biggest names on the left side of the political spectrum, like former President Obama, New York Mayor-elect Zohran Mamdani, and Vermont Independent Sen. Bernie Sanders. Welch in particular has gone viral for testy exchanges with former Chicago Mayor Rahm Emanuel and New Jersey Sen. Cory Booker.  Kara and Jennifer talk about what it's like to be a liberal atheist in the Bible Belt, why Jennifer finds centrist Democrats so frustrating, and why she’s skeptical about Georgia Republican Rep. Marjorie Taylor Greene’s recent break with Trump. They also talk about what Democrats get wrong about red states, and what she thinks the party needs to do to appeal to voters outside the coasts and big cities.  Please note: The original interview for this episode was taped Friday morning, before Greene announced her decision to resign from Congress and Mamdani met with Trump. We taped a second interview on Saturday morning to get Jennifer’s reaction to the news.  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

Political commentator Scott Jennings has been called the “conservative explaining Red America to CNN viewers.” As the in-house Republican on CNN’s NewsNight With Abby Phillips debate panels, he often acts as a de facto Trump spokesman at the table. Jennings has been in Republican politics for more than two decades. In the mid-aughts he worked as a Special Assistant to President George W. Bush, and later advised Kentucky Senator Mitch McConnell in multiple campaigns. Jennings was openly critical of President Trump before and during his first term, especially after the January 6th attacks. But in his new book, A Revolution of Common Sense: How Donald Trump Stormed Washington and Fought for Western Civilization, Jennings argues that Donald Trump’s second term is not just a political comeback, but a transformation of the presidency itself. Kara and Scott spar about the Epstein files, discuss what they mean for the MAGA movement, and whether Trump’s policies are really “common sense.” Plus, how Scott turned into a MAGA man and why he likes being the odd-Republican-out at CNN. Note to listeners: This is an extended version of the episode that was originally published on Thursday, November 20th. 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