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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.”
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In this episode of On with Kara Swisher, Swisher interviews actor and comedian Jeff Hiller, who reflects on his late-career breakthrough, his Emmy-winning role on Somebody Somewhere, and his current roles in Pluribus and Widow’s Bay. The conversation explores the challenges of being a character actor, the impact of industry consolidation and AI on Hollywood, and the emotional resonance of authentic representation in storytelling.
Gina Raimondo, former U.S. Secretary of Commerce and Governor of Rhode Island, expresses deep concern about the U.S. unpreparedness for AI-driven workforce disruption, rating her worry at a 9 out of 10. While bullish on AI’s potential to accelerate innovation and economic growth, she warns of massive job displacement—especially among white-collar, clerical, and middle-aged workers—and calls for urgent policy innovation, corporate accountability, and a national strategy centered on worker transition, not just retraining.
Ben Wikler argues that American democracy is under existential threat from concentrated wealth and power, particularly from figures like Elon Musk, and that the only way to save it is through a permanent, grassroots-driven campaign to unrig the political system at every level. The 2025 Wisconsin Supreme Court race, where Musk-backed Brad Schimmel lost despite massive spending, proved that democracy can withstand even the most extreme financial assaults when people organize locally and authentically. The key is not just winning elections, but building durable infrastructure that listens to voters, earns trust, and focuses on structural reforms—like abolishing the filibuster and enacting the National Popular Vote—that can break the cycle of instability and deliver real change.
The Democratic Party is undergoing a profound generational and ideological transformation, driven by a wave of progressive, anti-establishment candidates who are channeling deep voter frustration with the status quo—on issues ranging from Gaza and policing to housing, child care, and economic insecurity. While the party’s old guard often responds by attacking the left, the real threat isn’t ideological diversity but the failure to listen to its base, especially young voters and people of color. The energy behind insurgent candidates like those backed by the Democratic Socialists of America (DSA) and figures like Zohran Mamdani offers a path to durable power—if Democrats can balance authenticity with electability, avoid top-down kingmaking, and stop treating their own voters as the enemy. The upcoming Michigan Senate primary between Haley Stevens and Abdul El-Sayed will be a critical test of whether progressive energy can translate into general election success in a purple state.
The convergence of AI and cybersecurity is creating an unprecedented threat landscape where nation-state-level hacking capabilities are becoming democratized, enabling even low-tier adversaries like North Korea to conduct sophisticated cyber operations. The erosion of U.S. cybersecurity infrastructure and politicization of agencies like CISA further compound the risk.
Donald Trump's second term, as chronicled in Maggie Haberman and Jonathan Swan's book Regime Change, is portrayed as a presidency unmoored from historical norms, marked by extreme centralization of power, rampant corruption, and the full embrace of tech and business leaders who once resisted him. The administration operates with near-total impunity, enabled by a loyalist Justice Department, a cowed Republican Congress, and a Supreme Court immunity ruling, while Trump leverages his authority to enrich himself and his family.
Non-consensual deepfake pornography has evolved from a niche threat targeting celebrities to a widespread epidemic affecting ordinary people, especially young women and teens. Enabled by increasingly accessible AI tools and lax platform enforcement, these synthetic images and videos are being weaponized for harassment, abuse, and profit — often with devastating psychological consequences for victims. Despite emerging laws like the Take It Down Act and growing public awareness, enforcement remains weak, platforms evade accountability, and creators of deepfake content face little to no legal repercussions.
The internet increasingly feels artificial and manipulated, not because every piece is fake, but because synthetic content—AI-generated text, music, video, and bot-driven engagement—now dominates platforms, creating a pervasive sense of paranoia and disorientation. This shift isn't just technological; it's philosophical, challenging our sense of agency, reality, and what it means to be human online.
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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.”
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