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The Gray Area with Sean Illing

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The Gray Area with Sean Illing
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  • America is losing big on sports betting
    Almost every tech platform is designed to grab and hold your attention, to keep you clicking, scrolling, and buying for as long as possible. Sports gambling has become one of the clearest examples of this. The industry has created frictionless apps on your phone that let you bet on everything from March Madness to a pregame coin toss to who wins a minor league British dart tournament. While betting has become easier — and arguably fun — the cost of these apps is much higher than the money that is won and lost on them. Today’s guest is Jonathan D. Cohen, author of Losing Big: America's Reckless Bet on Sports Gambling. He and Sean discuss the rise of sports betting, why the industry targets young men in their advertising, the social costs of frictionless sports gambling, and how the industry could be improved. Host: Sean Illing (@SeanIlling) Guest: Jonathan D. Cohen, writer and author of Losing Big: America's Reckless Bet on Sports Gambling We would love to hear from you. To tell us what we thought of this episode, email us at [email protected] or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of ⁠The Gray Area on YouTube⁠. Listen to The Gray Area ad-free by becoming a Vox Member: ⁠vox.com/members⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  • It’s time to get weird
    The internet was supposed to set us free. But somewhere along the way, it became a tool for surveillance, extraction, and control. What happened? And is there still time to reclaim the weird, untapped potential of the digital world? This week, Sean is joined by Douglas Rushkoff. He’s a media theorist, author of Survival of the Richest and Team Human, and host of the Team Human podcast. They trace the arc of the internet from its utopian beginnings to its corporate capture, and explore what it would take to build something different. Along the way, they talk about the loss of weirdness, the logic of capitalism, the dangers of scale, and the difference between systems thinking and systems feeling. They also reflect on whether it’s still possible to use technology to foster a more connected and communal life. Host: Sean Illing (@SeanIlling) Guest: Douglas Rushkoff, media theorist and host of Team Human We’d love to hear from you. Email us at [email protected] or leave a voicemail at 1-800-214-5749. Your questions and feedback help us make a better show. Watch full episodes of The Gray Area on YouTube. Listen ad-free by becoming a Vox Member: vox.com/members Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  • What if humans went extinct next Friday?
    What comes after the human? We’re living through multiple crises — ecological, technological, political. But beneath all of that is something even deeper: a crisis of the self. Who are we, really? How did we come to see ourselves as separate from the world, from each other, from the systems that sustain us? And what if that way of thinking is what got us into this mess? Today’s guest is Mark C. Taylor, philosopher, cultural critic, and author of After the Human. Mark and Sean discuss the philosophical roots of climate change, the dangers of individualism, the false promise of techno-utopianism, and what it might mean to shift from seeing ourselves as isolated egos to members of a vast, interdependent web. They talk about AI, death, Hegel, Descartes, hope, and why ideas matter. Host: Sean Illing (@SeanIlling) Guest: Mark C. Taylor, philosopher and author of After the Human: A Philosophy for the Future. We would love to hear from you. To tell us what we thought of this episode, email us at [email protected] or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  • Can college survive Trump?
    American higher education is under attack. Project 2025 laid out the battle plan pretty clearly: Get rid of the Department of Education, shut off federal funding, take control of the accreditation system, and take down diversity, equity, and inclusion programs. And in the end, change what students are encouraged to study and what professors are allowed to teach. The questions we’re left with is why? And is it working? Today’s guest is Michael Roth, president of Wesleyan University. He’s a vocal defender of higher education. But he’s also honest about where things have gone wrong and what needs to change. Michael and Sean discuss the Trump administration’s efforts to change universities and colleges, the potential societal effects of that effort, political biases on campus, the dangers of ideological conformity, and the value of a college education (what is even the point of going to college any more?). Host: Sean Illing (@SeanIlling)Guest: Michael Roth, president of Wesleyan University and author of numerous books including Beyond the University: Why Liberal Education Matters and The Student: A Short History. Mentioned in this episode: Host Sean Illing’s interview with reporter James Walsh about AI on campuses. We would love to hear from you. To tell us what we thought of this episode, email us at [email protected] or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members And you can watch new episodes of The Gray Area on YouTube. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  • Hopeful pessimism
    We live in a culture obsessed with hope. We are trained to believe that being hopeful is the key to success. Stay positive. The sun will come out tomorrow. Keep the faith. But maintaining that kind of blind hope is hard. When our hopes are dashed, we often feel defeated. In a world that’s filled with lots of dark clouds and very few silver linings, perhaps we need a better way to balance our hope and our pessimism. In today’s episode, Sean interviews philosopher Mara van der Lugt about her new book Hopeful Pessimism. The two talk about how to sustain hope when you’re feeling pessimistic, the pitfalls of blind hope, and what the climate movement can teach us about staying motivated when success is unlikely. Host: Sean Illing (@SeanIlling)Guest: Mara van der Lugt, lecturer in philosophy at the University of St Andrews and author of Hopeful Pessimism. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members Learn more about your ad choices. Visit podcastchoices.com/adchoices
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About The Gray Area with Sean Illing

The Gray Area with Sean Illing takes a philosophy-minded look at culture, technology, politics, and the world of ideas. Each week, we invite a guest to explore a question or topic that matters. From the the state of democracy, to the struggle with depression and anxiety, to the nature of identity in the digital age, each episode looks for nuance and honesty in the most important conversations of our time. New episodes drop every Monday. From the Vox Media Podcast Network.
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